14 Local Spots for Dining alfresco around Winchester

On the right day, nothing beats a relaxed outdoor meal at a great restaurant, especially during these times.  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

Image from 50/50 Taphouse Facebook Page

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

Image by Winchester-Frederick County Tourism

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


Image from Bonnie Blue Facebook Page

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)


Image from Creekside Facebook Page

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

Image courtesy George’s Food & Spirits

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


Image from Oakstone Pizza Instagram Page

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

Old Town Walking Mall (multiple restaurants)

Winchester/Old Town

Image by Winchester-Frederick County Tourism Office

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!

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

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

Espresso Bar & Café – Full espresso bar and some pastries; front and rear patios available. B/L

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

Papermill Place


This no-frills local favorite diner is hopping most mornings. We suggest you take a look here before heading to one of those big chain breakfast spots – you’ll get big servings of good food here for great prices. They offer a nice side patio with umbrellas for dining outside. B/L/D

Piccadilly’s Public House

Winchester/Old Town

Image from Piccadilly Public House Facebook Page

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

Image by Winchester-Frederick County Tourism

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


Image by Winchester-Frederick County Tourism

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

Umberto’s Pizza & Pasta

Winchester/Delco Plaza

Image from Umberto’s Facebook Page

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!