Where to get burgers in Winchester: Old Town and the south side

Last checked 2026-10-20. Refreshed every three months.

Most of Winchester’s burgers are in Old Town, where pubs and grills on the Loudoun Street Mall and Cork Street all list them. Outside downtown, Five Guys and two Wendy’s restaurants cover the Pleasant Valley Road area and Berryville Avenue by Interstate 81.

How we made this list. The places come from OpenStreetMap records inside Winchester’s city limits, the same data behind our local directory, checked against each place’s own website on 2026-10-20. Snow White Grill’s web address no longer loads; it is kept because the Friends of Old Town directory lists it on the mall. The list is alphabetical. It is not a ranking or a recommendation, and nobody paid to be on it. Run one of these places? Write to us to correct your entry.

The list

The places

50/50 Taphouse takes its name from 50 taps and 50 burgers. Any burger on its menu can be swapped for a house-made veggie burger or grilled chicken. Call for reservations.

Cork Street Tavern says it has served Old Town for 40 years and is family-owned. Its menu has a sandwiches and burgers section, and it has a patio dining room and a fireplace room.

Five Guys on Adams Drive is the burger and fries chain’s Winchester store. Its page lists dine-in, takeout, delivery and outdoor seating.

Macado’s is a Virginia sandwich chain that began in Roanoke in 1978, and it bills itself for overstuffed sandwiches, burgers and wings.

Snow White Grill is a grill on the mall listed in the Friends of Old Town directory; OpenStreetMap records it as a burger and fries counter. Its web address returned an error on 2026-10-20.

Union Jack Pub and Restaurant is a British-style pub in the Victorian-era Union Bank Building on the mall, now under new ownership. It lists burgers, sandwiches and salads beside its pub fare.

Wendy’s has two restaurants inside the city, on Berryville Avenue and South Pleasant Valley Road. Both list drive-thru, breakfast and late-night hours.

The Winchester Tavern is a downstairs cocktail bar on the mall whose handhelds include an apple butter smash burger. It opens at 4 p.m. and is walk-in only.

Water Street Kitchen at the south end of the mall lists Lucy’s Burger, a double-patty Black Angus burger, beside all-day breakfast and Southern plates. Its patio faces the mall.

More lists

Wings, pizza, patios and outdoor dining, all our eating lists, the local directory and restaurant inspections.

Frequently asked questions

Where can I get a burger in Winchester?

There are 10 places inside the city limits: 50/50 Taphouse, Cork Street Tavern, Macado’s, Snow White Grill, Union Jack Pub, The Winchester Tavern and Water Street Kitchen in Old Town, Five Guys on Adams Drive and two Wendy’s restaurants.

Where can I get a burger late at night in Winchester?

Both Wendy’s restaurants, at 1100 Berryville Ave. and 2185 S. Pleasant Valley Road, list hours to 1 a.m. daily. In Old Town, Union Jack Pub lists 1 a.m. on Friday and Saturday.

Where can I get a burger in Old Town Winchester?

Snow White Grill is at 159 N. Loudoun St. on the mall. Macado’s, Union Jack, Water Street Kitchen and The Winchester Tavern on the mall and 50/50 Taphouse and Cork Street Tavern on Cork Street also list burgers.

Where can I eat a burger outside in Winchester?

Five Guys on Adams Drive lists outdoor seating, Water Street Kitchen has a patio facing the mall, and Cork Street Tavern has a patio dining room.