Dining & Libations

Union Jack Pub & Restaurant

The Union Jack Pub & Restaurant is housed in the Victorian cast iron Union Bank Building which has been restored at it was originally in 1878, mak...

Brewbakers Restaurant

Enjoy award-winning food and drinks at Winchester’s favorite restaurant and bar. Indoor dining or outdoor café on the Old Town Walking Mall.

Village Square Restaurant

Contemporary American cuisine in Old Town Winchester. Large patio, private dining rooms, piano bar, beautiful atmosphere. Business lunches and dinners...

Thai Winchester

Full service restaurant with patio seating and full bar, featuring authentic Thai cuisine and drinks. Winner: “2009 People’s Favorite Restaurant” awar...

Cork Street Tavern

Cork Street Tavern was established in 1985. With over 25 years of passion and experience, the staff continues to uphold the custom of excellence the t...

George’s Food and Spirits

George’s Food and Spirits, located in the historic and award winning George Washington Hotel in charming Downtown Winchester, Virginia.  For dec...

Espresso Bar & Café

The French Pressed coffee is excellent. Also enjoyed the nice atmosphere over sandwiches with a friend. The pricing is good so if you want coffee down...

La Nicoise Café

Savor wonderful French food at La Niçoise Café, a cozy café nestled firmly within the heart of Winchester, Virginia and the beautiful Shenandoah Valle...

Old Town Snow White Grill

The Old Town Snow White Grill is a quaint old fashioned diner, best known for the original mini-burger. Opened in 1948, the grill opened as a family c...

Violino Ristorante Italiano

Violino Ristorante Italiano offers made-from-scratch, creative, culinary dishes by Italian chefs Franco and Marcella Franco.  Aside from the fantastic...

Milano’s Ristorante & Bar

Come enjoy a drink at Milano’s while you watch the big game!  We also have a bar menu including appetizer items and sandwiches.  Check out a liv...

Italian Touch

Italian Touch has all of your favorite Italian cuisine for eat-in, takeout, and delivery for all of Winchester.  Come in for our daily lunch and dinne...

Awabi Sushi Bar

Awabi serves only the freshest sushi and authentic Japanese cuisine.  We also serve Japanese beer and sake, so come in for a taste of Japan!

Red Fox Creamery

Red Fox Creamery (formerly Middleburg Creamery) started our operation making homemade ice cream in Middleburg Va. Our retail store in Middleburg offer...

Aroma Deli

Aroma Deli is a deli and coffee bar that specializes in Peruvian rotisserie chicken that can be smelled around the block.  Their specialty coffees als...

Water Street Kitchen

Down home cooking in Historic Downtown Winchester Virginia. Chef Dan Kalber’s take on classic Americana cuisine, Utilizing locally sourced ingredients...

147 North

Located at 147 North Loudoun Street, 147 North offers American cuisine with daily specials.  Come in for live music on weekends as well as a blues jam...

Chop Stick Cafe

Located at the corner of Piccadilly Street and Kent Street, Chop Stick Cafe is a Thai restaurant with many Asian specialties and sushi.

Joe’s Steakhouse

Dine Within the Walls of History Joe’s Steakhouse is located in the historic Philip Williams House. The circa 1820s historic building features a two-s...

Roma Old Town

Roma Old Town, a local favorite gathering place on the historic walking mall in Winchester, embodies the same level of freshness, originality, and val...

50/50 Taphouse

We believe the best Pairing is Beer and Burgers. With 50 Taps and 50 Burgers you can pair them together as you so desire. We are all here to have fun....

The Black Rose Coffee/Tea Lounge

The Black Rose Coffee/Tea Lounge offers French Press made to order Coffee Drinks, Teas & Chai Teas.  We have Mexican Hot Chocolate, and Kid friend...

The Hideaway Café

The Hideaway Café is a one-of-a-kind coffee house, eatery, and community gathering space in Old Town, Winchester–a true Main Street Community in...

Winchester Brew Works

Winchester Brew Works is a nanobrewery one block north of the Old Town Loudoun Street Mall. Serving modern, flavorful brews in a family-friendly tasti...

Alesatian Brewing Co.

Alesatian Brewing Co. is a local nanobrewery that brings fresh, unique, and classic brews to the heart of Old Town Winchester, VA. It’s located ...

Chopped Corner Tacos

Chopped Corner Tacos, operated by the owners of Chop Stick Cafe, offer authentic Mexican cuisine.

Bright Box Dining

Already recognized as one of the top 50 small music venues in America, Bright Box aims to further create an amazing experience for ALL the senses by s...

V2 Raw Bar

V2 Raw Bar offers casual dining and several private dining rooms. Up until the recent past, this building housed the Miller’s Drug Store, once the old...

Sexi Mexi Burritos

Sexi-Mexi food is a freshly prepared, cross-cultural fusion that knows no boundaries – made with a blend of regionally sourced and home-made ingredien...

Benny Meleto’s

Benny Meleto’s is now open! Benny’s is the home of the Virginia slice with locations all over the state.