15 Local Spots (31 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 toddler and an infant 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.  As always, if I missed something, let me know and I’ll be happy to add it!

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

50/50 TaphouseWinchester/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 DeliWinchester/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 – Winchester

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 & BakeryWinchester

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 Station – Winchester/Kernstown

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.  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

Joe’s Steakhouse – Winchester/Old Town

Another great restaurant just steps from the Loudoun Street Walking Mall, Joe’s offers top-notch steaks and seafood in a beautiful, authentic southern mansion setting. Their outdoor dining patio has intimate evening lighting but can still feel the energy of the nearby mall. SB/L/D

Nana’s Irish PubMiddletown

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 (aka Loudoun Street Mall) RestaurantsWinchester/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 secret rear patios. B/L

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

Snow White Grill – Tiny, classic no-frills grill; no better place for a slider! 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

Village Market & Bistro – Upscale bistro with many craft beer & wine options. L/D

Village Square Restaurant – Upscale dining, piano bar & lounge located next door.  L/D

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

Piccadilly’s Public HouseWinchester/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 117Lake 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 DiningStephens 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

Stephen’s Jazz Cafe – Winchester

Yes, Winchester has a really cool jazz cafe. Located just up Kent St and next to jazz musician John Kirby’s childhood home, this cafe turns out great southern food and lots of live jazz.  Their outdoor seating area is rocking year-round – the nearby SU Conservatory students provide fresh talent all through the school months.  L/D

Sweet NOLA’s – Winchester

This is another new 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.  Some limited outdoor seating available.  L/D

Umberto’s Pizza & PastaWinchester/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!