A guide to Old Town Winchester and the car-free Loudoun Street Mall: museums, food, parking, the DORA sip-and-stroll zone, murals and walking tours.

Last checked Oct. 19, 2026. Facts come from Friends of Old Town, the visitors bureau and the City of Winchester, linked below.

Old Town Winchester is the city’s historic downtown and its main gathering place: a 45-block National Register historic district built around the Loudoun Street Mall, a car-free brick walking mall lined with restaurants, shops, breweries and museums. The city counts more than 35 restaurants and 60 shops in Old Town, and the visitors bureau says the mall’s renovation was finished in 2013 (visitors bureau; city trail page).

Before you go

Getting there and parking

Old Town has four parking garages, which the city calls autoparks, plus on-street meters and surface lots. Meters are enforced 9 a.m. to 6 p.m. Monday to Friday; parking at meters is free after 6 p.m., on Saturdays and Sundays and on city holidays (city parking page). Handley Library has no lot of its own; its garages are about a block away.

The mall is for walkers only. City code requires cyclists to walk their bikes on the Loudoun Street Mall, and skates and skateboards are banned there. The Green Circle Trail runs along the south half of the mall, with a signed bike route around it on Clifford and Washington streets (trails guide).

Museums and landmarks

  • Shenandoah Valley Civil War Museum, 20 N. Loudoun St., in the 1840 Frederick County courthouse that served as a hospital and prison during the Civil War.
  • George Washington’s Office Museum, 32 W. Cork St., an 18th-century log and stone building, 540-662-4412.
  • Stonewall Jackson’s Headquarters, 415 N. Braddock St., Jackson’s headquarters in the winter of 1861-62, 540-773-1604.
  • Handley Library, 100 W. Piccadilly St., the domed main library, with weekly programs for young children.
  • Shenandoah Valley Discovery Museum, 19 W. Cork St., four floors of hands-on exhibits for young children.
  • Patsy Cline Historic House, 608 S. Kent St., a short walk south of the mall.

Addresses and descriptions are from the visitors bureau’s history and museums listings. More in our history and landmarks guide.

Food, drink and music

Old Town’s restaurants and small breweries run from diners and bakeries on Piccadilly Street to the pubs, taprooms and wine bars on and off the mall. Bright Box Theater, 15 N. Loudoun St., is the downtown stage for music and comedy. See our guides to brunch, live music and nightlife and date night, and the Friends of Old Town directory to eat, sip and shop.

Sip and stroll: the DORA

Old Town takes part in Virginia’s Designated Outdoor Refreshment Area program, which Friends of Old Town calls Old Town Spirit. During approved event hours only, people 21 and older can buy a drink at a participating restaurant or brewery and carry it outdoors within the marked area. Drinks must be in disposable cups of 16 ounces or less marked with the business name, and shops decide whether to allow drinks inside (look for the DORA YES or DORA NO sign). The standard zone is the walking mall from Cork Street to Piccadilly Street; a larger zone covering parts of Braddock, Cork, Kent and Piccadilly streets is used only for city events such as Winter Village. Events that use the DORA include First Fridays, Celtic Fest, Rockin’ Independence Eve and HalloWinchester (DORA information).

Events through the year

Old Town hosts the Shenandoah Apple Blossom Festival, Kidz Fest, Rockin’ Independence Eve, First Fridays, the Winchester Winter Village and a New Year’s Eve celebration, among others, according to the visitors bureau. Dates are on the Friends of Old Town calendar. Seasonal guides: Christmas parade and tree lighting, New Year’s Eve and Fourth of July fireworks.

Tours, murals and markets

  • Guided walking tours of Old Town run on some weekends from May to October, starting at the Kurtz Building, 2 N. Cameron St.; call 540-542-1326 or see the guided tours page.
  • History of Us, self-guided walking tours from Friends of Old Town about the buildings and the people and businesses behind them (Friends of Old Town).
  • Old Town Mural Trail, more than a dozen murals in alleys, on facades and inside businesses, including two Patsy Cline murals, at 210 S. Indian Alley and on the Jiffy Sandwich Shop at 331 W. Boscawen St. (mural trail map).
  • Winchester Farmers Market, in the parking area of the Working Man’s Store, 325 W. Boscawen St., Tuesdays and Saturdays; see our farmers markets guide.

What this means for you

  • Visit on a weekend or after 6 p.m. and the meters are free.
  • Leave the bike at a rack: the mall is walk-only.
  • For drinks on the mall, wait for a DORA event and look for the marked cups and signs.

Related: things to do this month, free things to do and getting around.

Frequently asked questions

Where do I park in Old Town Winchester?

Old Town has four parking garages open around the clock, plus street meters and lots. Meters are enforced 9 a.m. to 6 p.m. Monday to Friday and are free on weekends, after 6 p.m. and on city holidays.

Can you drink outside in Old Town Winchester?

Only during set events. Old Town takes part in Virginia’s Designated Outdoor Refreshment Area program, which lets people 21 and older carry drinks bought from participating businesses in marked 16-ounce cups along the walking mall, from Cork Street to Piccadilly Street, during approved event hours.

Can I ride a bike on the Loudoun Street Mall?

No. City code requires cyclists to walk their bikes on the Loudoun Street Mall, and skateboards and skates are not allowed.

Are there walking tours of Old Town Winchester?

Yes. The visitors bureau runs guided walking tours on some weekends from May to October from the Kurtz Building, 2 N. Cameron St., and Friends of Old Town publishes self-guided History of Us tours.