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...
Big L’s Bagels
Best Bagel Ever.
Broken Window Brewing Co.
Premier Nano Brewery specializing in a wide variety of craft beers located in downtown Winchester.
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 ...
El Centro Classic Mexican Food & Drink
El Centro Classic Mexican Food and Drink is located in the center of Winchester on the Old Town Walking Mall at 1 N Loudoun. From our amazing homemad...
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...
Lloyd’s Tropical Island Coffee and Café
Come enjoy authentic Jamaican coffee and cuisine at Lloyd’s Tropical Island Coffee and Café, where even the service is authentic Jamaican: pleas...
Macado’s
Macado’s Winchester is now open!
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...
Piccadilly Public House & Restaurant
Built in 1900 as a grocery warehouse, 125 E. Piccadilly Street in Winchester, Virginia has been restored to its roots in feeding the public. As you n...
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...