Dining & Libations

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....

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 ...

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...

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!

Benny Meleto’s

Carrying on Benedito’s name, “Meleto’s” means apple orchard in Italian and ties the great apple region at this northern point of Virginia back t...

Chop Stick Cafe

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

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...

Dividing Creek Beer Co.

Nano brewery in the heart of Old Town Winchester, serving up to 12 fresh styles every day from traditional, German styles to small-batch experimental ...

Espresso Bar & Café

Come enjoy freshly brewed coffee, espresso beverages, teas; assorted pastries, soup & sandwiches! Great atmosphere, free wifi for our customers. F...

Gringo Gordo Empanada Shop

Gringo Gordo is Northern Virginia’s best kept secret, serving authentic, Argentinian empanadas made-from-scratch. Our obsession with perfecting these ...

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...

Knead Bread

This family-owned and operated business was inspired by our father, Damiano Mazzone, 1st generation Italian who arrived in this country at Ellis Islan...

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...

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...

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...

Piccadilly Grill Diner

The Piccadilly Grill has served Winchester residents and visitors alike for over 50 years. In May 2019, Abed Sam Warden became owner and chef at the l...

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...

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...

Sabai Thai Winchester

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

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...

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...

The Wine Room at Taylor Pavilion

The Wine Room at Taylor Pavilion, located in historic Old Town Winchester, brings a fresh new destination for wine lovers to the vibrant downtown scen...

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...

Uno Pizzeria & Grill

It all began when Ike Sewell imagined a pizza unlike any other. Fresh dough with a tall edge, topped with homemade sauce and more cheese than you coul...

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...

Village Square Restaurant

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

Violino Ristorante Italiano

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

Water Street Kitchen

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

Willie Sutton’s Saloon

We are a classic American bistro and bar located in the heart of the historic downtown Winchester walking mall housed in the landmark Farmer’s a...

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...