15 Winchester Area Live Music Hot-Spots

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Flickr image by Richele Cole (embedded), taken at the Bright Box Theater

It took a few months of living here (probably because I have two little kids in my house) to start to grasp the depth of the live music scene in the Winchester area.  With all of the hyper-talented SU Conservatory students floating about our community, I figured there were live performances going on all over the place.  Now, after devoting some serious time to find out about more and more cool spots to catch some live tunes, I decided it might be nice to try and put it all down in one place.  As always, if I missed something here, don’t hesitate to let me know.  And get out there and enjoy!



Backseat Bar and Grill

Image from Backseat Bar & Grill’s Facebook page

Country, blues and acoustic fill much (but not all) of the regular live music bill at this local favorite eatery. 104 Full House Dr, Winchester, VA 22603; (540) 665-9033. Click here for a schedule of upcoming shows.


Blue Fox Billiards

Flickr image by PhyllisLynn (embedded)

Local, regional and national acts including country, metal, bluegrass and more. 1160 Millwood Pike, Winchester, VA 22602; (540) 665-2114. Click here for a schedule of upcoming shows.


The Bright Box

Blue Heaven
Flickr image by Tyler Priola (embedded)

Local, regional and national acts of every kind located in the heart of Old Town Winchester. 15 N Loudoun St, Winchester, VA 22601; (540) 665-2878. Click here for a schedule of upcoming shows.


Escutcheon Brewing Co

Image from Escutcheon’s Facebook page

Winchester’s original craft brewery features regular acoustic shows in their tasting room area. 142 W Commercial St, Winchester, VA 22601; (540) 773-3042. Click here for a schedule of upcoming shows.


Hopscotch Coffee & Records

Live Music at Hopscotch Coffee and Records

Image of Fletcher C. Johnson performing from Hopscotch Coffee & Records Facebook Page

One of our popular local coffee spots, patronized regularly by nearby Shenandoah University students. Occasional acoustic live music on tap in this eclectic coffee/record shop with outstanding locally roasted beans; (540) 514-5356. Click here for a schedule of upcoming shows.



Image of Engine No. 9 from Mimosa’s Facebook Page

This local Asian fusion restaurant offers an open mic every Thursday, as well as regular local original artists from country to jazz to electronic dance music (EDM). 202 Grocery Ave # 101, Winchester, VA 22602; (540) 545-8482.  Click here for a schedule of upcoming shows.


Nana’s Irish Pub & Restaurant

Image of Rick Harris from Nana’s Irish Pub’s Facebook Page

Live Irish, bluegrass, and rock music is performed weekly at this hidden gem of great Irish fare and live music right in the middle of Middletown, just steps from the new Gingerwolf Distillery. 7843 Main St, Middletown, VA 22645; (540) 868-9877. Click here for a schedule of upcoming shows.


Shenandoah University

Conservatory Presents 2014 Holiday Gala Concert
Flickr image by Shenandoah University (embedded)

The world-class SU Conservatory turns out regular musical offerings year-round, from free, open rehearsals to nationally known conductors to their ever-popular Summer Music Theatre program.  620 Millwood Ave, Winchester, VA; (540) 665-4569.  Click here for a schedule of upcoming shows.


Sweet NOLA’s Restaurant

Image from Sweet NOLA’s Facebook page

Live music, nationally recognized bands, and crazy-good Southern New Orleans-style food (“Food so good you need a safe word” according to their bumper sticker) in an intimate, funky cool setting.  688 N Loudoun St, Winchester, VA; (540) 667-6652.  Click here for a schedule of upcoming shows.



~Old Town Walking Mall Restaurants~


147 North

Image from 147 North’s Facebook page

An energetic blend of open mic nights, acoustic bands, and even EDM fill 147’s busy weekend music calendar.  147 N Loudoun St, Winchester, VA; (540) 313-4804.  Click here for a schedule of upcoming shows.


Brewbaker’s Restaurant

Image from Brewbaker’s Facebook page

Local and regional live music, many times in conjunction with Shenandoah University.  168 N Loudoun St, Winchester, VA; (540) 535-0111.  Click here for a schedule of upcoming shows.


Piccadilly Public House

Weekly piano bar on Wednesday and Thursday is juxtaposed with lively regional cover bands of every type acoustic performances on weekends.  125 E Piccadilly St, Winchester, VA; (540) 535-1899.  Click here for a schedule of upcoming shows.


Java Kava Bar

Live music at Java Kava Winchester from Facebook
Image from Java Kava’s Facebook page

Sip fresh kava or coffee here at Virginia’s first kava bar while enjoying local young talent performing live (sometimes scheduled, sometimes not!). 16 S Loudoun St, Winchester, VA; (540) 313-7199.  Click here for a schedule of upcoming shows.




James Charles Winery

Someone To Ride The River With

Flickr image by Coy Ferrell (embedded)

Live music every Friday and Saturday evening throughout the year, featuring a range of local, acoustic and SU conservatory performers and beautiful mountain views. 4063 Middle Rd, Winchester, VA; (540) 931-4386. Click here for a schedule of upcoming shows.


Valerie Hill Vineyard & Winery

Image from Valerie Hill’s Facebook page

Enjoy regular acoustic shows on weekends throughout the year in a historic, intimate setting.  1687 Marlboro Rd, Stephens City, VA; (540) 869-9567.  Click here for a schedule of upcoming shows.


The 2019 Guide to Halloween in Winchester

Excited for Halloween, but not sure what to do? Don’t freak out! Instead, let out a sigh of relief because we’ve got you covered. Here is a guide compiling some of Winchester’s Halloween happenings all throughout the month.

Blog post by Winchester-Frederick County Tourism intern, Paige Bridgeforth

Hill High Farm Presents: Haunted Nightmares and Other Events

Prepare to face your greatest fears at Hill High Farm’s Haunted Nightmares haunted house attraction. The house will be open through November 1st, 2019. For younger guests, they will be open during daylight hours on Saturdays and Sundays with a less-intense show. If you are eager for more scares, also check out The Last Ride. This is a “buried alive” simulator where you can lay in a casket to see what it’s like while still being able to get out afterwards. If spooky isn’t your cup of tea, they will also be hosting a slew of other activities such as escape rooms, a moonlit hayride, and a corn maze. For more information on these activities and their hours of operations for the haunted house, visit the Hill High Farm website. 933 Barley Lane, Winchester, VA 22602 Hill High Farm

Easely Created 

In the spirit of the season, Easely Created will be hosting a slew of Halloween-themed nights all throughout the month of October – and each night offers a different finished product. A sample of classes include: Hocus Pocus Door Hanger Paint Class, Hocus Pocus Sign DIY Workshop Class, and All Ages ‘The Great Pumpkin’ Paint Day 16×20 Canvas. New to painting? That’s okay! These classes are intended for anyone interested in painting and for all levels! For more information on specific classes and dates, check out their website. 47 W Boscawen St, Winchester, VA 22601

Courtesy of Easely Created’s Facebook Page

Worlds Away Escape: Redstar Sanatorium

Grab a few of your friends and head downtown to check out the latest escape room by Worlds Away Escape. The recommended number of players is 4-6 with 8 being max capacity. This room is horror-themed and features loud audio/music with strobe/flashing lights. Think you can solve the way out? For more information on this room, their other offered rooms, and for booking, check out their website. 9 N Loudoun Street, Suite 105, Winchester, VA 22601

Courtesy of Worlds Away Escape Website

October Happy Hour Run/Halloween Scavenger Hunt

Grab your sneakers because its time for Runner in Training‘s monthly happy hour run, but this time is different! This run will be in conjunction with their 3rd annual Halloween Scavenger Hunt. On October 18th, 2019 from 6pm-9pm, teams will have exactly one hour to race across Winchester finding the items needed and taking photos. Return back to Escutcheon Brewery to see which team ends up with the most points. Whether you win or lose, everyone can finish the evening off with a fresh pint. 141 W Commercial St, Winchester, VA 22601

Courtesy of Runner in Training’s Facebook Page

1st Annual Spooktacular Ball

Double, double toil and trouble! Come grab a Witches’ Brew or a Bloody Mary at this year’s Spooktacular Halloween Ball.  The Youth Development Center‘s first annual ball will be on October 19th, 2019 from 6pm-10pm. With your brew in hand, dance away the night to music performed by Meisha Herron Band. Take part in the costume contest by wearing your most hauntingly spooky costume. Also, expect to see a silent auction, door prizes, a dance competition, a cash bar, and more to be announced. Tickets can be purchased ahead of time on their website. The YDC said it best with, “It’s going to be a howling good time!” 3 Battaile Drive, Winchester, VA 22601

Halloween Trunk-or-Treat and Costume Contest

So great, it’s happening twice! The Family Drive-In will be hosting their annual Trunk-or-Treat and Costume Contest on Saturday, October 19th and Saturday, October 26th, 2019 from 5pm-7pm. As you go from trunk to trunk, make sure to catch the magic shows being performed by Kevin Owens, the face painting station, and an assortment of games. Don’t forget your best costume because there will be a costume contest with categories for children, teens, adults, and pets. The show is only beginning once trunk-or-treating is over! Screen 1 will show new releases Maleficent: Mistress of Evil and The Addams Family (2019) and over on screen 2 will be Zombieland: Double Tap and Joker. Keep checking their website or their Facebook page for when tickets go on sale. 5890 Valley Pike, Stephens City, VA 22655

Olde Towne Halloween Faire

Things are about to get a little bit spooky along the Loudoun Street Mall. This year, don’t just expect the usual trick-or-treating. The Olde Towne Halloween Faire will take place on Saturday, October 26th, 2019 from 4pm-7pm. Along with trick-or-treating, look for all kinds of new games and activities from kids of all ages. As you stroll along admiring the decorated storefronts, each participating business will be hosting their own game or activity. Some of these games include: Polka Dot Pot will be having a “Witches’ Hat Ring Toss” and Murphy Beverage Company will host “Mummy Bowling.” Once the sun goes down, the faire doesn’t end there. Head over to the Taylor Pavilion for a viewing of a Halloween classic, “Hocus Pocus,” or go on the family-friendly Apparition Trail tour to get a glimpse at the haunted history surrounding the Old Town Mall. 136 S Loudoun St, Winchester, VA 22601

Adults-Only Halloween Bash

Ghosts, goblins, and ghouls! Oh, my! All creatures are welcome for this creepy evening at the winery. On Saturday, October 26th, 2019, James Charles Winery & Vineyard has got you covered for an Adults-only Halloween Bash from 8pm-Midnight. As the rhythmic beats of BKDJ Paramount keep the night going, try a glass of Witch’s Brew! A glass of brew is included with the ticket purchase and additional glasses are only $5. Sexi-Mexi will be on-site serving up a wonderful selection of food for the evening. But don’t leave before 10pm or risk missing the costume contest. Prizes will go out to the best female, best male, and best couples costume. Tickets can be purchased online in advanced on their website or at the door, but beware. If the event is sold out, door tickets will not be available. 4063 Middle Rd, Winchester, VA 22602

Courtesy of James Charles Winery & Vineyard Facebook Page

Haunted History Ghost Tours

Ever wondered where the spirits of Winchester lie? These guided tours give you an in depth look at the mysteries found in Winchester’s history. As you glide along the streets and through the buildings of Old Town, the expert guide will tell historic tales and true ghost stories. There are three chances to go on this tour, Saturday, October 26th, Wednesday, October 30th, and Thursday, October 31st, 2019, all starting at 6pm. The tour lasts approximately one hour. Tickets for the tour must be bought in advance at the Winchester-Frederick County Visitors Center (1400 S. Pleasant Valley Rd, Winchester, VA 22601). Tickets are $10 and can be purchased with cash or check only. Each tour has a limit of 25 participants. For more information, call (540)-542-1326. Be prepared to have this tour leave you with goosebumps! Tour meets on the intersection of Cork St. and Loudoun St. Mall

History and Hauntings 

On Saturday, October 26th and Thursday, October 31st, 2019, the history of Valerie Hill Winery’s Manor House comes alive. Their ever-popular event known as “History & Hauntings,” allows guests the opportunity to listen to stories of first-hand accounts of experiences with the residential ghosts – such as the famous woman in the cellar that calls for help, and the spirit of a boy perpetually locked in the attic. Tickets include dinner by Village Square Restaurant, a glass of wine of your choice, and a detailed tour of the Manor House which focuses on the history and documented paranormal activity. This event is for adults 21 and over. For information on the event, check out their website. 1687 Malboro Road, Stephens City, VA 22655

Photo Courtesy of Valerie Hill Winery’s Website

8 of Winchester’s Can’t-Be-Missed Fall Festivals of 2019

As summer comes to a close and schools are back in session, don’t expect there to be a shortage on things to do in the area. As we welcome in the time of breezy weather and leaf-covered grounds, make sure to keep an eye on these eight fall festivals. What better way to say goodbye to summer than by celebrating the approaching autumn.

Blog post by Winchester-Frederick County Tourism intern, Paige Bridgeforth

Shenandoah Valley Apple Harvest Festival

Start off autumn right with this local favorite! The Shenandoah Valley Apple Harvest Festival is a two-day event that takes place on Saturday, September 21, 2019 from 10am-5pm and Sunday, September 22, 2019 from 10am-5pm. With the attendance growing further into the thousands each year, you can expect all the fun fall elements that have made it such a huge hit – plus new activities that have not been done before! To get your apple fix, make sure to be there for the apple pie eating contest on Sunday at 3pm, the apple pie baking contest, or the on-site apple butter making station. For the kids, look for the newly added Bubbleball by Wonderfly Games on Sunday from 12pm-5pm or the kidszone area with inflatables. Pets are welcome at this festival too, so bring them along to enjoy the canine obstacle course on Saturday. All proceeds made at the Apple Harvest Festival are donated to local non-profits. Find a full list of all this festival has to offer here.

250 Fairground Rd, Clear Brook, VA 22624

Winchester Brew Works Fall Festival

Welcome in the new season with the release of Winchester Brew Works traditional German Oktoberfest lager. Winchester Brew Works will be hosting a fall festival October 5, 2019 from 12pm-6pm to unveil their new lager and to serve up local fall-style beers. If lagers aren’t your thing, don’t worry! There will also be IPAs, ciders, and wine to offer a wide selection. Pair your beer with great food. Crash-Test Yummies will be on site serving German-style food all day. Stop by for a relaxing, chill day full of pumpkin beer and German cuisine.

2504 N Frederick Pike, Winchester, VA 22601

Marker-Miller Orchards Farm Market Apple Harvest Festival

Join Marker-Miller Farm Market on Saturday, October 12, 2019 from 9am-5pm and Sunday, October 13, 2019 from 10am-5pm in welcoming the harvest into town. Everything under the sun to do with apples is going to be there including apple cobbler and apple cider slushees. With over 20 varieties of apples, you can walk the orchards while picking your own, or you can buy a bushel from the market. While enjoying all of the apple treats the market has to offer, listen to the live music that will be playing from 1-3pm. While you enjoy the music, kids can have fun with the cow train, playground, and wagon rides running all day long.

3035 Cedar Creek Grade, Winchester, VA 22602


Photo courtesy Old Town Winchester

A German invasion is happening in Old Town Winchester on Friday, October 11, 2019 from 5pm-11pm and Saturday, October 12, 2019 from 12pm-8pm. This annual festival brings alive the traditions of the Bavarian culture. While walking the Loudoun Street Mall, expect to see street performers, free caricature paintings, a free photo booth, and live music by the Continentals. New attractions to the festival this year are a keg tapping ceremony with Austrian horses and the first ever Bürgermeister crowning. Don’t forget your lederhosen or dirndl for the best dressed contest! General admission is free, but for tastings you must buy a package. The online advanced tasting package is $20 which includes six tastings and a 12 oz glass beer stein. The day-of tasting packages are $25 which also include six tastings and a 12 oz glass beer stein.

136 S Loudoun St, Winchester, VA, 22601

Peak Leaf Music & Brewers Festival

Photo Courtesy of Peak Leaf Music & Brewers Festival’s Facebook Page

Want to know what’s better than enjoying a craft beer with some live music? Enjoying that craft beer with live music to support a great cause. The Peak Leaf Music & Brewers Festival in Middletown, VA is a one day festival on October 19, 2019 that brings together live music, local brews, and food to help kids in this area. A portion of the proceeds go towards providing under-served students in the Frederick County area with school meals. Tickets can be purchased online for $35 and kids under 12 are free. Gates for parking open at 10:30am, but the gates are open to the public at 11am. The live music ends at 7pm, but the festival will close at 8pm. For a full list of musical acts and vendors in attendance, check out their website.

Corner of State Rt 634 and Rt 11, Middletown, VA, 22645

Richard’s Fruit Market Apple Festival

Richard’s Fruit Market of Middletown, VA will be hosting their yearly Apple Festival on Saturday, October 19, 2019 from 11am-4pm. This festival will have yard games, yummy farm to table concession stand, hay wagon rides, a petting zoo, and live bluegrass music playing from 12pm-3pm. It is free to get into the festival, however prices will vary on concession stand products or anything the market has to offer.

6410 Middle Rd, Middletown, VA 22645

West Oaks Farm Market’s Fall Festival

Join West Oaks Farm Market for their second annual Fall Festival, the best festival of the year! The festival will be held on October 19, 2019 from 9am-6pm, and is for all ages. Families welcome! Expect a wide variety of activities from a corn maze, a pumpkin patch, hayrides, an apple cannon, a bounce house, face painting, and much more. From 1pm-5pm, one of Winchester’s favorite local bands, Trainwreck, will perform.

4305 Middle Road, Winchester, VA, 22602

Ravenwood Faire

Calling all knights and maidens! Winchester, VA is getting their first ever renaissance fair at the Frederick County Fairgrounds on October 26 and 27, 2019 from 10am-7pm. This fair is jam packed with everything medieval including fire dancers, jousting knights, drum circles, Celtic dancers, theatrical shows, and live music by Merlin’s Beard. Crafters like Adventure Armoury and American Highlander Kilts will be present to help you dress the part. Local food vendors such as BroBears, Ambrosia Catering, and Creative Concessions will provide enough food for a hearty feast. Fill up your chalice with selections from locals like Winchester Brew Works, Alesatian Brewing, Escutcheon Brewery, Winchester CiderWorks, and Misty Mountain Meadworks.

250 Fairground Road, Clear Brook, VA 22624

10 Ice Cream, Custard and Cool Treat Hotspots around Winchester


Okay, let me begin by saying this area has a serious addiction to ice cream.  And let me be clear that this isn’t a criticism in any way.  In fact, pair this with the affinity for great coffee (see our local coffee shops post), and you’re pretty much set when you visit over the summer.

Now, I’ve occasionally had to make some tough sacrifices for this job, and one of them is the many ice cream cones I’ve had to eat in order to accurately write this blog.  You’re welcome.  Somebody had to do it.

Seriously, though, I sincerely hope you have a chance to check out at least one or two of the below listed shops the next time you’re in the Winchester area (by the way, don’t hesitate to let us know if I missed anything!).

Ice Cream

A&L Scoops and Swirls

Our southernmost sweet tooth haven, this small family-owned ice cream shop offers up soft serve, scoop ice cream and a full ice cream menu, with many delicious desserts to choose from.  Located just down the street from Lord Fairfax Community College, they’ve got that coveted outside patio seating to fully enjoy our beautiful, laid back warm summer evenings.  7597 Main St, Middletown, VA 22645

CD’s Coffee and Cream

Image by Winchester-Frederick County Tourism

Craig and Diana (the C and D of this establishment) have carved out a very busy little spot here on Rt 50 just a minute or two west of Valley Health Hospital. The best of both worlds, you can have your caffeine and sugar fix at the same time here. Featuring single origin volcanic soil coffee and locally made Garber’s ice cream, this is a must stop when exploring our beautiful countryside!  2953 Northwestern Turnpike, Winchester, VA 22602

Cooter’s Ice Cream

Owner Ken, a transplant from Georgia, is about as genuinely kind and Southerly as you can get.  Don’t go in a hurry; he makes every customer feel incredibly welcome and appreciated.  What else can we say – cold ice cream, warm smiles.  Features a rotating variety of Hershey’s ice cream, milk shakes and malts, and incredible banana splits.  **Temporarily closed with a new location hopefully coming soon**

New Town Creamery

Opened in early 2014, this husband and wife operation took the place of the former McCoy’s Dairy Bar.  This completely new ownership has made high quality, fun foods their focus.  In addition to regionally sourced ice cream, they have an array of quick summer foods like hot dogs, funnnel cakes and fries.  And be careful, they’ll deep fry just about anything.  Their Easter special?  Deep fried Cadbury eggs.  Their summer best seller?  Deep fried Oreo cookies…  320 Fairfax Pike, Stephens City, VA 22655

Red Fox Creamery & Country Store

Owners Kathy and Brian Lewis opened Middleburg Creamery in 1996, and relocated to the Old Town Winchester pedestrian mall in late 2010.  This is a true creamery that makes everything from scratch.  Kathy is the ice cream guru, whipping up many great classic and seasonal flavors.  Far from just a creamery, though, they have a scratch kitchen that turns out local favorites like chicken salad, rotisserie chicken, chili, soups, baked goods and more. 146 N Loudoun St, Winchester, VA 22601 

Frozen Custard

Pack’s Frozen Custard / Dairy Corner (4 locations)

Image by Winchester-Frederick County Tourism

Pack’s is a local institution – a regional chain started several decades ago by the one and only Mrs. Pack – where you’ll get a very similar but not identical experience at each of our four local remaining locations.  When Mrs. Pack retired a few years ago, we understand that the locations were bought by either close family or long-time employees.  Now, a word to the wise, if you’ve never had true custard before, take it easy Chief.  This is some seriously rich awesomeness in a cone.  And go prepared for a line, especially on Friday and Saturday evenings all summer.

1) 177 Dairy Corner Pl, Winchester, VA 22602 (the original location) – Facebook page link

2) 2021 N Frederick Pike (522 North), Winchester, VA 22603 – Facebook page link

3) 2580 Northwestern Pike (Hwy 50), Winchester, VA 22603 – Facebook page link

4) 380 Fairfax Pike, Stephens City, VA 22655

0-60 Energy Cafe – Valley Avenue

This one of two 0-60 Energy Cafe locations in the Winchester area, but the only one that serves up custard and Italian ice. Located in a former Rita’s Italian Ice building, the owners decided to keep on offering the very popular frozen custard, Italian ice, and “gelati” which is a layered version of these two frozen treats. Don’t worry, you can still get your outstanding coffee, breakfast sandwiches and grilled cheeses here, too. Best of all, they’re open year-round so you don’t have to wait until spring to get your custard fix! 2430 Valley Ave, Winchester, VA 22601


Disclaimer – no businesses paid us or gave us anything to be on this list – we just love sweet treats and our local businesses, as we hope you do when you visit!



15 Local Spots (29 total restaurants) for Dining alfresco around Winchester

On the right day, nothing beats a relaxed outdoor meal at a great restaurant.  When my wife and I are looking for a place to eat, outdoor dining is a huge plus because, well, we’ve got a little girl and a toddler and aside from a generally more laid back atmosphere, any noise our kids make just seems much quieter outside.

Fortunately for us, we’ve got an over-abundance of both perfect days here in the northern Shenandoah Valley as well as restaurants with outdoor dining for every budget and taste.  In fact, Old Town Winchester has the largest concentration of alfresco dining in the entire Shenandoah Valley!

B=Breakfast, SB=Sunday Brunch, L=Lunch, D=Dinner

50/50 Taphouse

Winchester/Old Town

If you want a burger and/or a beer, well, they’ve got 50 kinds of each here (hence their name).  They have a huge indoor space but you can also score a great seat in their enclosed, partially shaded outdoor seating area.  Located just steps from the Loudoun Street Mall and next to the Shenandoah Valley Discovery Museum.  L/D

Aroma Deli

Winchester/Old Town

Breakfast served most days until around 11am.  This local favorite has great rotisserie chicken with a Peruvian flair, burritos, and of course breakfast.  They’re located in a historic house about 2 blocks from the Loudoun Street Mall, and you can eat outside on their porch or patio.  Mature trees and umbrellas provide shade during the heat of the afternoon.  B/L/D

Backseat Bar and Grill


This casual diner staple is always busy turning out dishes to hungry customers, whether it be hearty breakfasts or great burgers and sandwiches for lunch or dinner.  They’ve added a pretty large outdoor seating area in the parking lot that lets you enjoy our cooler mornings and evenings most of the year.  B/L/D

Bonnie Blue Southern Market & Bakery


This fairly recent addition to the area’s family of restaurants has the feel that it’s been here for generations.  Very popular for their breakfast and barbecue, this great find has fresh coffee and great pastries as well.  Umbrella covered picnic style seating outside is more lively than intimate. B/L/(D on Fridays)

Creekside Town Center (multiple restaurants)


This outdoor shopping area has recently become a dining hotspot, with nearly all of their restaurants offering alfresco dining.  Located in Kernstown just minutes from the extremely popular Alamo Drafthouse, this upscale area is quite a find.  Below are the restaurants offering alfresco dining:

The Butcher Station – Local farm-to-fork hotspot with burgers and seasonal items. Also a stop on the Virginia Oyster Trail. L/D

The Chocolate Café – Creative sandwiches, fresh bakery goods, and covered patio dining. L

Firefly Café & Bakery – Fast casual, fresh sandwiches and bakery goods with a social mission.  SB/B/L

I J Cann’s American Grill – Casual, affordable upscale American cuisine.  SB/L/D

George’s Food and Spirits

Old Town Winchester

The attached upscale casual restaurant to the beautiful George Washington Hotel, this lower level dining experience boasts an intimate, relaxed atmosphere just a block from the Loudoun Street Mall.  And believe it or not, they were the first inland stop on the famous Virginia Oyster Trail.  Limited outdoor seating available.  B/L/D

Oak Stone Craft Pizza & Bar


This very popular craft pizza joint is located across the beautiful Handley High School, and offers a large brick patio seating area. They have a very creative menu offering outstanding pizzas but also a variety of sandwiches and dinner entrees.  SB/L/D

Nana’s Irish Pub


Traditional Irish fare with a creative flair and full bar with an authentic Irish atmosphere and live music on weekends.  The patio seating is located out back and provides a cozy, private setting with views west towards the mountains.  L/D

Old Town Walking Mall (multiple restaurants)

Winchester/Old Town

This is the biggest concentrated hub of alfresco dining options in the entire Shenandoah Valley.  Nearly every restaurant has taken advantage of the beautiful, recently renovated Loudoun Street Mall on Loudoun St.  We’ll just list out all of the ones with alfresco dining so you can relax and people watch any day of the week, year-round!

147 North – Creative American cuisine and full bar; live music on weekends. L/D

Awabi Sushi Bar – Extensive and creative sushi menu, beer, sake and wine. L/D

Brewbaker’s – Very popular local American style restaurant and bar; live entertainment. L/D

El Centro – Classic Mexican food and very popular margaritas. L/D

Espresso Bar & Café – Full espresso bar and some pastries; front and

Old Town Snow White Grill – Tiny, classic no-frills grill; no better place for a slider! L/D

Roma Wood-Fired Pizza – Local Italian in a cozy atmosphere; craft brewery located upstairs. L/D

Thai Winchester – Award-winning chef-created Thai food. L/D

Union Jack Pub & Restaurant – Famous fish & chips, creative pub fare, many beers on tap. L/D

Water Street Kitchen – Traditional Southern cuisine favorites in the heart of the walking mall. L/D

Village Square Restaurant – Upscale chef-inspired dining with an oyster bar.  L/D

Violino Ristorante Italiano – Upscale, family owned authentic Italian landmark restaurant. L/D

Piccadilly’s Public House

Winchester/Old Town

Popular for lunch but usually hopping for dinner and after, the large outdoor seating area here offers a peaceful afternoon meal spot or energetic evening scene with sports games often projected on the side of the adjacent building.  Burgers, sandwiches, wings, salads and a full pub menu promise something for every taste.  L/D

Region’s 117

Lake Frederick

This brand new addition to our family of unique local restaurants boasts lake-view dining with some outstanding locally-sourced menu items.  Casual visitors are encouraged to grab a cup of coffee or espresso from their separate grab and go counter and relax outside on the elevated deck on huge hanging sofas (they’re too nice to be called swings).  This is a great stop before or after a few hours kayaking or fishing on Lake Frederick.  SB/L/D

Roma Casual Italian & Greek Dining

Stephens City

A very popular local Mediterranean (Greek & Italian) restaurant.  The Stephens City location has a small but comfortable outdoor seating area.  See Old Town Winchester section for other location.  L/D

Shaffer’s BBQ & Market


This is the least fancy entry on our list, but it possibly offers the best views. This very popular and locally-focused BBQ market in a former gas station has a picnic shelter that overlooks the Cedar Creek & Belle Grove National Historic Park and the Appalachian Mountains. They also offer lots of locally sourced goodies, such as local beer, canned goods, cider, and more. Definitely worth a stop! B/L/D

Sweet NOLA’s


This is another newer addition to the Winchester area dining scene, and has rocketed to the top of most lists.  Authentic New Orleans style food, live jazz, and a funky, fun atmosphere have cemented this restaurant as a favorite for locals and visitors alike.  Limited outdoor seating available.  L/D

Umberto’s Pizza & Pasta

Winchester/Delco Plaza

Too hot or cold outside?  Well, you can still get your alfresco dining fix at Umberto’s.  Their outdoor dining patio is, well, inside.  They offer inside inside dining as well. Very popular Italian cuisine and pizzas keep the tables filled at this unexpected gem. L/D


As always, no business paid to be on this list – we just love dining outdoors and wanted to share a thorough list of the bounty of offerings we have.  Enjoy!


11 Tasty Cups of Coffee in Winchester

I must admit, when my wife and I first scouted out the Winchester area, we immediately went online to see if there were any good local coffee shops. They’re just one of those underlying indicators of a community’s style. Just about any town can have a Starbucks or Dunkin (and yes, the Winchester area has several of each). However, not all of them have enough ‘flavor’ for a successful purveyor of a great local cup of joe. I’ve been to, and enjoyed, all of these spots, so here’s what I found (in no particular order). I sincerely hope you have a chance to check out at least one or two of these the next time you’re in the Winchester area. ~Justin

Hopscotch Coffee

Hopscotch Coffee and Records in Winchester. Image by Winchester-Frederick County Tourism.

These guys know their coffee; in fact that’s what dominates their menu, addition to a few small pastry offerings. They offer their own special roasts of local award-winning roaster Lone Oak Coffee. Situated in what feels like an old garage, they’ve got a unique 2-story set up where you enter upstairs, then below is the seating, and live music area. And get this – they even have a record shop attached. Seriously cool. 250 Millwood Ave, Winchester, VA 22601 Free wifi.  

Bro Bears Drive-Thru Coffee

A friendly smile, free with every cup! Image courtesy Bro Bears Facebook page.

Great coffee, friendly smiles, quick service, teensy-tinsy workspace. Owned by a disabled veteran and his wife (and Michigan natives, to boot), this tiny shop just off I-81 at Exit 315 turns out high quality beverages and has quickly become a local favorite. They offer keto coffee, a full espresso menu, locally made mini donuts, and cold drinks as well. You can stop and walk up to the window if you like, but most of their business comes from their drive-through. Tucked down in the parking lot of the Harbor Freight shopping center. 1141 Berryville Ave, Winchester, VA 22601.


Steamy’s in Winchester. Image by Robert Harris for Winchester-Frederick County Tourism.

Want some fresh homemade bagels? Yes, Steamy’s makes their own unique craft bagels in-house in very small batches. Their coffee is also expertly crafted, and they have an intimate, eclectic space that is exactly what you envision a college town coffee shop to look like. This is a great place to warm up (or cool down, depending on the weather) and watch the city go by. Located just steps from the Old Town Winchester pedestrian mall, this is a must for visiting on a chilly or drizzly day. 38 E Piccadilly St, Winchester, VA 22601Free wifi.

0-60 Energy Café

0-60 Energy Cafe in Winchester. Image by Winchester-Frederick County Tourism.

One of the more unique settings for a coffee shop; but don’t let the race car enthusiast interior or strip mall location fool you – this is some outstanding, artisan coffee. Their specialty is cold drip coffee, but they’ve also got some fresh made breakfast and lunch menu items. Make sure to check out their full grilled cheese menu! 170-11 Delco Plaza, Winchester, VA 22602. Free wifi.

Espresso Bar & Café

Espresso Bar and Cafe in Old Town Winchester. Image by Winchester-Frederick County Tourism.

This modern coffee shop, ideally located right on the Old Town Winchester pedestrian mall, is reminiscent of some European coffee shops we’ve seen – clean but cozy, with local artwork adorning the walls. They’ve got a few breakfast items like a breakfast sandwich and, our favorite, the locally made and incredibly rich little Irish tea breads. Cuddle up and sneak out back to the secret garden (pictured above) to enjoy your cup of coffee, or sit out front and people watch on the mall. 165 N Loudoun St, Winchester, VA 22601. Free wifi.

JoGail’s Country Cookin’ Restaurant

Image by Winchester-Frederick County Tourism

We just had to get this on the list – just about the opposite setting of a college town coffee shop, this local favorite turns out a two kinds of coffee – small and large. But boy, is this place hopping at 7am on a weekday. Heavily favored by locals, you’ll feel right at home no matter where you’re visiting from. The smiles are just as warm as the coffee, and the setting offers a nice view of the mountains and valley. Located just 20 minutes (but a world away) from downtown Winchester on Rt 50. 5665 Northwestern Pike, Gore, VA 22637.

Firefly Café & Bakery

This made our list as, in addition to a great cup of coffee roasted by Orange County Roasters out of Orange, VA (drip as well as espresso drinks), their food is fresh and fantastic. Lots of specials, incredible homemade desserts, friendly and happy employees, and a California flair that somehow fits just right in our community. And for a little dose of philanthropy to sweeten your coffee, they’ve got a long and ingrained history of employing folks with disabilities and other barriers to employment. 3035 Valley Ave. #101, Winchester, VA 22601. Free wifi.

Tropical Island Coffee Café

Welcome to our very own Little Jamaica here in Winchester. Jamaican Blue Mountain coffee (the legit stuff; not the mixed down blends you see so often) is brewed up daily here. But this is a whole Jamaican cuisine experience – including an incredible jerk chicken, curry goat, beef ox-tails and even a variety of York Castle ice cream flavors. Just can’t do without your espresso? They’ve got a full espresso bar menu as well. Located right around the corner from the Old Town Winchester pedestrian mall, directly across from the beautiful Handley Library. 39 W Piccadilly St, Winchester, VA 22601Free wifi.

The Hideaway Café

Hideaway Cafe in Old Town Winchester. Image by Winchester-Frederick County Tourism.

This coffee shop originally truly earned it’s name. Why? Well, they started in the basement of the old post office building in Old Town, just across the street from Handley Library. In early 2018 they moved to a much more visible and accessible spot at the southern end of the Old Town Winchester pedestrian mall, very near the Shenandoah Valley Discovery Museum. They have become a fixture of local university students and evening shoppers and diners, and have begun offering sandwiches and other in-house baked goodies. 141 S Loudoun St, Winchester, VA 22601. Free Wifi.

Bonnie Blue Southern Market and Bakery

Bonnie Blue Cafe in Winchester. Image by Robert Harris for Winchester-Frederick County Tourism.

This local hot spot for tourists and locals alike offers up very hearty cups of French-press coffee all day. You can find a variety of additional offerings here, including daily homemade pastries and muffins, a full lunch menu, and even local goods like hickory syrup, local eggs, and local brews. If you look closely, you can see the faded word Hopscotch on a counter near the entrance – this is where one of our other popular shops got it’s start several years ago. 334 W Boscawen St, Winchester, VA 22601Free wifi.

CD’s Coffee and Cream

A chocolate covered cherry frozen coffee at CD’s Coffee and Cream in Winchester. Image by Winchester-Frederick County Tourism.

One of Winchester’s newest coffee shops is in a fairly unexpected location. Situated in a small storefront on U.S. 50 about 5 minutes west of Valley Health hospital, this unassuming little combination coffee shop and ice cream parlor stays very busy year-round. They brew up an exclusive single origin Laos volcanic ash-grown light or dark roast, which is also available in whole bean (they grind for free on-site). You can also find shaved ice here in the summer. And don’t let the name fool you – CD’s stands for owners Craig and Diana, not the disc 🙂 Tip: try the chocolate covered cherry frozen coffee. 2953 Northwestern Turnpike, Winchester, VA 22602. Free wifi.


* Disclaimer – no businesses paid us or gave us anything to be on this list – we just love coffee and our local businesses, as we hope you do when you visit!


12 Tempting Homemade Breakfast Spots Around Winchester

The good old greasy spoon breakfast is alive and well in Winchester and surrounding Frederick County. While we have our share of upscale dining in the area, often times nothing beats a hearty home-cooked breakfast. We’re very fortunate to have a wide array of spots located all through the region to satisfy your craving for eggs, bacon, pancakes, waffles and yes, most even have scrapple and grits. Here’s a list, in no particular order, of these great spots!

Papermill Place Restaurant

This is one of, if not the most crowded breakfast spots in the area. Locals and visitors of all walks of life pile in here every morning of the week year-round. The coffee is hot, the kitchen is quick, and the staff is brimming with southern hospitality. Kids will love the “Millie’s pancake,” which is shaped like their favorite cartoon mouse. (540) 667-1136. 2214 Papermill Rd, Winchester, VA 22601. Breakfast served all day. Facebook page.

Bonnie Blue Southern Market & Bakery

Bonnie Blue Cafe in Winchester. Image by Robert Harris for Winchester-Frederick County Tourism.

Located in a renovated Esso gas station, this very unique and exceptionally popular spot offers very large southern style breakfasts (try the homemade biscuits with locally cured bacon bits baked right in). You’ll also find a wide array of local products near the bakery case, including hickory syrup, farm raised eggs and local brews. (540) 686-7490. 334 W Boscawen St, Winchester, VA 22601. Breakfast served all day. Facebook page.


Steamy’s in Winchester. Image by Robert Harris for Winchester-Frederick County Tourism.

This coffee shop makes the list because of their extremely popular homemade bagels and the wide variety of breakfast bagel sandwiches and in-house baked goods that owner and guy-who-always-remembers-your-name Lenny Sweet creates on a daily basis. Open 7 days a week until around noon, this easy-access spot borders the north end of the Loudoun Street Pedestrian Mall in Old Town Winchester. 38 E Piccadilly St, Winchester, VA 22601. Breakfast served all day. Facebook page.

Lynette & Jerri’s Diner (Amherst Diner)

Lynette and Jerri’s Diner. Image by Winchester-Frederick County Tourism.

Located across the street from Bonnie Blue, this small traditional diner is very popular with locals, and offers counter and booth seating and quick service with a smile. Originally opened as the Amherst Diner in 1958, it was purchased by employees Lynette & Jerri in 2015 to keep the doors open and thriving. Interesting historic fact – famed polar explorer Rear Admiral Richard Byrd was raised next door (the original house is gone but a historical marker remains). (540) 504-7995. 334 Amherst St, Winchester, VA 22601. Breakfast served all day.

Sunnyside Café

A single hotcake at Sunnyside Cafe in Winchester. Image by Winchester-Frederick County Tourism.

This very small diner is easy to miss, but you definitely want to find this spot if you can! Owner Arlene is the greeter, waitress and chef at this tiny spot with about 5 tables, however she keeps your coffee cup hot and full and the plates are huge. Guests regularly recommend the biscuits and gravy, but supplies are limited! We recommend a single hotcake to start – wait and see how big it is before ordering more! (540) 678-1292. 1317 N Frederick Pike, Winchester, VA 22603. Breakfast served all day.

Granny’s Place

Want to have breakfast in one of Patsy Cline’s old haunts? Then this is the spot for you. Better known for their fried chicken dinners and evening live music, this rustic bar and grill surprisingly opens at 6am every morning for breakfast and is very kid-friendly with cartoons often playing on the flat screen TV’s during the early hours. Located on Rt 7 headed out of Winchester. (540) 313-4965. 2294 Berryville Pike, Winchester, VA 22603. Breakfast served all day. Facebook page.

Granny’s Pancake Cottage

Enjoying the same owners and similar menu as the Granny’s Place location on Rt 7, this smaller breakfast-focused location about 10 minutes south of Winchester in historic Stephens City is a go-to favorite for locals and visitors alike. Find all your home-cooked breakfast favorites on the menu here in a friendly, light atmosphere. Tip: you’ll usually find all you can eat pancake specials on Tuesday for about $5. (540) 508-2434. 5460 Main St, Stephens City, VA 22655. Breakfast served all day. Facebook page.

Piccadilly Grill Diner

Located just a few storefronts down from Steamy’s, this very intimate counter-service diner offers traditional breakfast favorites in a bustling setting right in Old Town Winchester. Street parking is available as well as garage parking across the street by the George Washington Hotel. (540) 722-7177. 46 E Piccadilly St, Winchester, VA 22601. Breakfast served all day. Facebook page.

Backseat Bar and Grill

Backseat Bar and Grill. Image by Winchester-Frederick County Tourism.

This is the go-to spot for all-day breakfast on the north end of Winchester. Serving up all sorts of diner classics (like burgers and fries) in addition to your favorite homemade breakfast dishes, this find is easily accessible from Hwy 37 just a minute or two from I-81. (540) 722-7177. 46 E Piccadilly St, Winchester, VA 22601. Breakfast served all day. Facebook page.

High Point Restaurant

High Point Diner in Stephens City. Image by Winchester-Frederick County Tourism.

Also located in the small historic town of Stephens City, this local diner pumps out plenty of breakfast comfort classics every morning. Tip: look nearby for a replica of ECTO 1 from the original Ghostbusters, which can occasionally be seen in the area! (540) 869-2469. 5106 Main St, Stephens City, VA 22655. Breakfast served all day. Facebook page.


Hayfield Family Restaurant

Breakfast at the Hayfield Family Restaurant. Image by Winchester-Frederick County Tourism.

This is a true country restaurant where you can rub elbows with the locals and meet some great folks. The menu is simple, the plates are as big as the smiles and the coffee is hot. Located about 10 minutes west of Winchester, this is a great spot to get a hot breakfast while exploring the countryside, visiting farm markets, or viewing foliage in the fall. (540) 877-1004. 5340 Northwestern Pike, Gore, VA 22637. Breakfast served until 11am.

JoGail’s Country Cookin’

Just up Hwy 50 from the Hayfield Family Restaurant is this very busy local favorite. Fast service, country smiles, and hearty servings are a benchmark here. This is yet another great spot to get a hot breakfast while exploring the countryside, visiting farm markets, or viewing foliage in the fall. (540) 877-1178. 5665 Northwestern Pike, Gore, VA 22637. Breakfast served all day. Facebook page.

New Year’s Eve Guide for the Winchester Area

Image from First Night Winchester Facebook page
Got kids? Got grandparents and family visiting? Maybe you’ve got a party spirit rearing to go. Or maybe you prefer to enjoy New Year’s Eve in a peaceful, quiet setting. No matter what, we’ve got you covered this New Year’s Eve in the Winchester and surrounding Frederick County area with some ideas on what to do from the day before to the day after.  Need help getting home safely?  We’ve got a number of cab companies and Uber!  Please note: Hours/events listed below have been checked before posting, however are subject to change.  Please double-check before making plans.

Kid and Family Friendly

30th Annual First Night Winchester

  • Saturday, December 31 – 10am-Midnight throughout the Old Town Winchester area, culminating with the Apple Drop at midnight on the walking mall.  Buttons $10 for adults, children under 10 are free.  Reserve buttons online here (with a $2 convenience fee), or purchase at these locations.

Museum of the Shenandoah Valley

  • Friday, December 30 – Open from 10am-4pm (regular admission prices).
  • Saturday, December 31 – Open from 10am-4pm as part of the part of First Night Winchester celebration (free admission with First Night Winchester botton).
  • Sunday, January 1 – Closed.

Shenandoah Valley Discovery Museum

  • Friday, December 30 – Open from 9am-5pm (regular admission prices).
  • Saturday, December 31 – Open from 12pm-4pm for the New Year’s at Noon event (regular admission prices), and later as part of First Night Winchester celebrations from 4pm-7pm (free admission with First Night Winchester botton).
  • Sunday, January 1 – Closed.

United Way/Rubbermaid Parking Lot Sale at the Apple Blossom Mall

  • Saturday, December 31 – Open from 8am-12pm – Very popular local event, with proceeds benefitting the Adult Care Center of the Northern Shenandoah Valley (free admission but show up early as the best items go fast!).

Walking in a Winter Wonderland

  • Friday, December 30 – Open from 5:30pm-9:30pm (regular non-peak admission prices).
  • Saturday, December 31 – Closed.
  • Sunday, January 1 – Open from 5:30pm-9:30pm – final day of the season (regular non-peak admission prices).

Winchester Model Railroad Club

  • Saturday, December 31 – Open from 6pm-10pm – part of First Night Winchester celebrations (free admission, First Night Winchester buttons not required, but donations accepted).

Party Spirit

Image from Sweet NOLA's Facebook Page Image of Sweet NOLA’s 2016 New Year’s Party from their Facebook Page

Alamo Drafthouse

  • Saturday, December 31 – 10pm-Midnight – “When Harry Met Sally” New Year’s Eve Party. Show starts at 10pm, special champagne toast at midnight.

Bright Box

  • Saturday, December 31 – 8pm-12:30am – “B105’s Boots Bourboun and Barbecue New Year’s Eve Bash” – live country music, dancing, fresh barbecue, and a bourboun toast at midnight.  $15 in advance or $20 at the door.  21+

Hideaway Cafe

  • Friday, December 30 – 8pm-10pm – Sashay Away 2016 Drag Show – admission $3

Sweet NOLA’s

  • Saturday, December 31 – 7:30pm-Midnight – New Orleans House of Blues circa 1940 New Year’s Eve Party with live music and 4 course buffet meal with incredible food.  $65 per person, reservations required.  21+

Winchester Brew Works

  • Saturday, December 31 – 8pm-Midnight – New Year’s Eve Brewery Bash with live music, dancing, light fare from eM, and beer.  $45 per person, reservations required. 21+

Winchester Beer Mile

  • Sunday, January 1 – 1pm-4pm – This national trend (as seen on CNN, ESPN, Jimmy Fallon, and more) is enjoying it’s second year in Winchester.  $20 registration, beer and root beer (non-alcoholic) categories. 21+

Valley Cat

  • Saturday, December 31 – 7:30pm-11pm – New Year’s Show & Afterparty featuring 5 live bands.  $10 cover, or $8 if you bring canned goods for donation to the Blue Ridge Area Food Bank.  All ages.

A Quiet Celebration

Just a sampling of local spots to enjoy on your own casual time with limited or no special events planned Image from Region’s 117 Facebook Page    

Belle Grove Plantation

  • Friday, December 30 – Open from 10am-8pm – final day of the season (regular admission prices).  Candlelight tours 6p-8p.

Escutcheon Brewing Co.

  • Friday, December 30 – Open from 2pm-10pm
  • Saturday, December 31 – Open from 12pm-6pm
  • Sunday, January 1 – Open from 12pm-8pm

James Charles Winery 

  • Friday, December 30 – Open from 12pm-8pm
  • Saturday, December 31 – Open from 12pm-4pm
  • Sunday, January 1 – Closed

Region’s 117 Restaurant

  • Friday, December 30 – Open from 11:30am-9pm (regular hours/menu)
  • Saturday, December 31 – Open from 11:30am-9pm (reservations only, special menu)
  • Sunday, January 1 – Open from 11am-3pm (brunch menu)

Valerie Hill Winery

  • Friday, December 30 – Open from 11am-9pm
  • Saturday, December 31 – Closed
  • Sunday, January 1 – Closed
  • Monday, January 2 – 11am-6pm New Year’s Party with live music by Jimmy Lee from 2-5

9 Ways to Pass a Rainy Day in Winchester

Rainy Day in Winchester by Aaron Riddle
Image courtesy Aaron Riddle Photography

We don’t get all of these beautiful natural surroundings for free here in the northern Shenandoah Valley – we must pay for them with the occasional rainy day. But don’t let that dampen your adventurous spirit or dash your hopes for a fulfilling visit. Here’s an inclement weather guide to help out the next time you’re in the Winchester area and the sun takes a day off…


1) Warm Up With a Cup of Coffee

Photo of Espresso Bar and Cafe by Winchester-Frederick Tourism

This can mark the beginning, middle or end of any day here in the area. Fortunately, we’ve got a pretty impressive array of local ‘joe’ hotspots that we’ve already listed out for you in our previous Coffee Hotspots blog. We even marked which ones have free wifi for you…


2) Discover a New Restaurant

Get your indoor al fresco dining fix at Umberto’s

We’ve got over 200 restaurants here in the Winchester & Frederick County area, so no excuses. Treat yourself to a fine dining experience somewhere like Joe’s SteakhouseGeorge’s Food & Spirits, Village Square, Violino Ristorante or Region’s 117 Lakefront Dining. Or maybe try one of our newer restaurants like Oak Stone Craft Pizza, Sclafani’s, Sweet NOLA’s, Paladin Bar & Grill or Smokey T’s Southern Kitchen.


3) Catch a Live Show

Image of the Bright Box from Facebook

Check out the calendars of Blue Fox, Brewbakers, the Bright Box, Stephen’s Jazz Café, SU Conservatory, Sweet NOLA’s, and the Winchester Little Theatre.


4) Catch a Canned Show (aka a Movie)

Image of the Alamo Drafthouse from their website

The Alamo Drafthouse is more than a top-notch, affordable movie theatre – they run a dizzying amount of special screenings, events and special programs. If you’ve got RainX on your windshield, the Family Drive-In is great on a rainy evening as you’ll avoid the crowds. And of course, we’ve got the AMC Theatre at the Apple Blossom Mall if you want to make an afternoon of it and wander around the mall.


5) Go Hiking

Image of small falls near Pinnacle Rock on the Tuscarora Trail by Winchester Tourism

Hiking on a drizzly day can be a transformative experience, as the earth comes alive in the rain and you’ll be at one with your surroundings. A couple of important caveats: a) thunder and lightning are a no-no, b) heavy rain can cause dangerous situations in the mountains, so be cautious and c) make sure you hit Mountain Trails outfitters in Old Town Winchester first to make sure you’ve got the gear, maps and local expertise to maximize your trip.


6) If You’ve Got Kids, Try These

Image of a brook trout at the Shenandoah Valley Discovery Museum by Winchester Tourism

The Alamo Drafthouse, the Shenandoah Valley Discovery Museum, the Apple Blossom Mall (has a kid’s play area), and the Museum of the Shenandoah Valley (check their site for current exhibits).


7) If Not, Have a Drink at One of These…

Image from Alesatian Brewing Co. Facebook page

…and be thankful for the rain as it’s growing more local grapes/hops/apples/grains that are used to make what you’re drinking. These are all on the brand new Shenandoah Spirits Trail, but we’ll break them down for you anyway. Breweries: Alesatian Brewing Co, Broken Window BrewingEscutcheon Brewing Co., Winchester Brew Works. Wineries: Briede Family Organic VineyardJames Charles Winery, Valerie Hill Winery. Cidery: Winchester Cider Works.


8) Finally Get to That Museum

Image of Abram’s Delight historic house by Winchester Tourism

Been looking for an excuse to get out to one of our great museums?  Now’s a perfect time.  Open year-round:  Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum, Old Court House Civil War Museum.  Open seasonally (check site for dates):  Abram’s Delight, Belle Grove Plantation, George Washington’s Office, Newtown History Museum (Stephens City), Patsy Cline House, Stonewall Jackson’s Headquarters Museum.


9) Or, the Default Rainy Day Activity: Go Shopping!

Image of shopping in Old Town Winchester by David Polivka

First, check out our Boutique Shopping Guide we created recently to get you around to all the cool, local boutique shops. But don’t stop there; our main shopping hotspots include:

And yes, if you insist, we even have a Costco 🙂


As always, no business paid to be on this list – we just wanted to help get you out of that nice hotel room and exploring, even if it is a bit rainy!

Top 10 Must-Do List for Fall Around Winchester

Fall starts in late September, and every year the localities throughout Virginia’s Shenandoah Valley gear up for the many travelers that come through from all over the region, nation and world.

Viewing our fall foliage is such an integral part of any trip here this time of year, we’ve just put an icon next to leaf-peeping related opportunities.

Our team has compiled a Top 10 list of Winchester area things you just can’t skip when visiting every year as the nights get cooler, the weather gets calmer, and our outdoor beauty comes into sharp focus.  Get out and enjoy!

#1 – Go to a farm market

Photo of Richard’s Fruit Market – source: Facebook

This season is their bread and butter, and for good reason.  You’ve got the big, ever-popular ones like Marker-MillerVirginia Farm Market, and West Oaks Farm Market and then some really unique and fun smaller finds like Hill High Farm, the Homestead Farm at Fruit Hill OrchardRichard’s Fruit Market, Rinker Orchards, and Shen Val Farm Market!

#2 – Turn off that GPS and go for a country drive 

Yes, I’m telling you to get lost (but seriously, in a friendly way) out on our local roads.  We’ve got fields, orchards, rolling hills and mountains all within about 20 minutes of Old Town Winchester.  Or if, like many of our fall visitors, you’re headed to the nearby Skyline Drive in the Shenandoah National Park, take a side road like 522 or 11 and enjoy the ride down and make a few discoveries along the way.

#3 – Roll up your sleeves and pick an apple 

Surprise, this is apple country.  I know you probably already knew that, but to really grasp the scale of it you’ve got to actually get into the trees at one of those orchards.  Marker-Miller and Rinker Orchards have pick-your-own operations, or just drive around the countryside and look for some “pick-your-own” signs.

#4 – Hike to a vista point, even if just for an hour or two 

The Tuscarora Trail is truly a hidden gem, but may not remain so once people realize there’s alternative for Old Rag to get beautiful valley vistas.  We’ll make it easy for you to get magnificent views of our fall foliage – get to Eagle Point overlook by clicking HERE and hiking about 1.75 miles northeast along the trail, or get to Pinnacle Rock (pictured) by clicking HERE and hiking less than 1 mile northwest along the access trial.  Need maps, gear, or just some local expertise?  Then Mountain Trails Outfitters on the Old Town Walking Mall is a necessary stop.

#5 – Enjoy a meal al fresco

This was our our lastest blog, but it was still a little warm when we posted it.  The evenings are perfect now – check out the list, choose at least one and enjoy!

#6 – Go on a horseback trail ride 

Photo of Rocking S Ranch – source: Facebook

Okay, we’ve got lots of options regionally for trail rides, and there’s a reason for that.  Our surrounding countryside in the Shenandoah Valley provides an incredible trail ride experience.  This is a must-do for young and old alike.  Check out our professional trail ride outfitters such as Bailey’s Walking After Midnight FarmMagic Mountain Farm, Raynor’s Hilltop Farm, the Rocking S Ranch (the #1 rated local attraction on Winchester’s TripAdvisor page), or the Wagon Wheel Ranch.

#7 – Have a local, seasonally brewed pint of beer or cider

Photo of Alesatian Brewing Co. – source: Facebook

In the very recent past, you couldn’t get a pint of locally crafted beer here.  Now we’ve got four different, unique and pretty awesome brewery options and an outstanding cidery.  Alesation Brewing Company, Broken Window BrewingWinchester Brew Works, Escutcheon Brewing Co. and Winchester Cider Works all have great fall offerings and on-site tastings.  These are all sites along the Shenandoah Spirits Trail, which pulls together every brewery, winery, cidery and distillery in the Northern Shenandoah Valley. Want traditional non-alcoholic apple cider?  You’ll find it at most local markets – Rinker’s apple cider is pretty famous.

#8 – Catch a show at the drive-in

Photo of Family Drive-In Theatre – source: Facebook

There are only seven drive-in theatres left in all of Virginia, so the Family Drive-In located just outside Stephens City is truly a special place.  Owner Jim Kopp has really captured the nostalgic allure of his theatre, and boy, does this place get busy. Open throughout the fall season (not just summer!) and offering special screenings of classic films.

#9 – Enjoy an annual fall festival

There are still many dedicated locals here who work hard during harvest season at our farms, orchards and vineyards.  To celebrate the end of harvest season, they like to blow of some steam and celebrate – fortunately, we’re all invited to many of these events!  Here’s a little sampling of the annual fall events in our area: Shenandoah Valley Apple Harvest Festival, Marker-Miller and Richard’s Apple Harvest Festivals, OctoBeer Fest, Pumpkin Festival, and Winchester Brew Works Oktoberfest.

#10 – Learn how to fly-fish (or at least tie a lure)

Photo of a free Winchester Trout Unlimited Barfly event at Escutcheon – source: Facebook

The local Winchester chapter of Trout Unlimited has regular “Bar Fly” social events that pair novice to experienced fly tying lessons with beer at local breweries, namely Escutcheon Brewing Co.  The good news is, if you snag your finger, it won’t hurt as much.  This is a great group to help guide visiting fisherman to the best trout spots in our area.  Want to go it alone?  Check out the interactive DGIF Virginia Trout Fishing map, which shows local stocked lakes & streams, cold water streams, and wild trout streams in our area.


As always, no business or individual paid to be on this list – it’s just a fun collection of some top fall activities that should keep you busy for this fall, and probably next fall as well!  Don’t be shy to let us know if we missed anything!.