Winchester is a town of 28,000 people (2020) in the Shenandoah Valley of Virginia, USA. The town is a good base for exploring the rest of the valley and a picturesque historical site in its own right.
The closest airport with scheduled commercial service is Washington Dulles International Airport, which is a 1-hour drive (51 miles, 82 km) from Winchester. From the airport, either rent a car or take a taxi to Winchester.
The closest passenger train station is in Martinsburg, West Virginia, a 30-minute drive (21 miles, 39 km) from Winchester.
The closest passenger bus station is in Washington, D.C., a 1-hour 30-minunte drive (79 miles, 127 km) from Winchester.
- Green Circle - The Green Circle is being developed to allow easy access between the Visitor Center and historic sites by bicycle or on foot.
- The trolley provides easy access around town.
- Several Limousine Companies are available for winery tours.
- 1 Stonewall Jackson's Headquarters, 415 N. Braddock St., ☏ .
- 2 Handley Library (Handley Regional Library), 100 W. Piccadilly Street (Corner of Rt. 7 and Rt. 11), ☏ . M-W 10AM-8PM, Th-Sa 10AM-5PM. A library ornately designed in the Beaux Arts style that opened to the public in 1913. Includes the Nancy Larrick Children's Room, the Middle Kingdom for teens, Information services and the Stewart Bell, Jr. Archives.
- 3 Tomb of Lord Fairfax. The final resting place of Thomas Fairfax, 6th Lord Fairfax of Cameron, the proprietor of all of Northern Virginia during colonial times. The tomb is on the grounds of the historic Christ Episcopal Church.
- 4 Shenandoah Valley Civil War Museum (Old Frederick County Courthouse). Civil war museum displaying local artifacts such as insignia and firearms, in a former courthouse built in 1940.
- 5 George Washington's Office (Adam Kurtz House).
- 6 Shenandoah Discovery Museum, 54 South Loudoun St. Open M-F 9AM-5PM, Sunday 1-5PM. Children's museum $5.
- 7 Mount Hebron Cemetery. Historic cemetery
- 10 Patsy Cline House. A mid-19th century two-story log cabin that was the childhood home of country singer Patsy Cline. It is now a museum.
- 11 Museum of the Shenandoah Valley. Local history and art museum.
- 12 Glen Burnie. 1794 mansion of Robert Wood, the son of the founder of Winchester. The home and gardens are part of the Museum of the Shenandoah Valley.
- 13 Shenandoah University.
- 14 Fort Collier. Largely intact Confederate fort
- 15 Star Fort. Earthwork star fort involved in the Second and Third Battles of Winchester. Free.
- 16 Marker-Miller Orchards, 3035 Cedar Creek Grade (Route 622) (15 minutes (7 miles, 11 km) west of the city), ☏ . Open July-December. Pick-your-own apples. Buy fruit, vegetables, and baked items.
- Apple Blossom Festival. Late April/Early May.
- Ghost Tour. Thrilling, chilling, one-and-one-half-hour easy-walking guided tour exploring the ghost haunts of historic downtown Winchester.
- Guided Walking Tour of Old Town Winchester, 2 N Cameron St, ☏ . May–Oct, 1st and 3rd Fridays at 6PM and 2nd and 4th Sundays at 4PM. $10.
- Civil War Walking Tour. Educational 1½-hour easy-walking guided tour exploring the events of the Civil War that were centered in historic downtown Winchester.
- Civil War Driving Tour. Educational four-hour escorted driving tour exploring the events of the Civil War that were centered in the Winchester area.
- Follow the Apple Trail. Stop at the Visitor Center by Abrams Delight and pick up a cassette or CD and take a leisurely drive through Winchester and Frederick County.
- 1 Bell's Fine Clothing, 122 N Loudoun St, ☏ . M-F 9:30AM-6PM, Sa 9:30AM-5PM, closed Su. Formal clothing.
- 2 Handworks, 150 N Loudoun St, ☏ . M-Th 10AM-6PM, F Sa 10AM-9PM, Su 11AM-5PM. Home goods.
- 3 Kimberly's, 135 N Braddock St, ☏ . M-Sa 10AM-6PM, Su 11AM-5PM. Boutique with clothing and gifts.
- 1 Snow White Grill, 159 N Loudoun St (Along the central pedestrian walkway), ☏ . A cheap and greasy local favorite that serves delicious mini-burgers, birch beer, and milkshakes. Eat inside or out.
- 2 Cork Street Tavern, 8 W Cork Street (In old town Winchester), ☏ . American food including ribs. Outdoor seating during summer.
- 1 50/50 Taphouse, 29 Cork St. M-W 4-10PM, Th 4-11PM, F Sa 11:30AM-11PM, Su 11:30AM-10PM. Beer and burgers
- 2 Alesatian Brewing Company, 21 N Loudoun St, ☏ . Tu-Th 4PM-9PM, F 4-10PM, Sa noon-10PM, Su noon-9PM, closed M. Brewery serving wood-fired pizza.
- 1 George Washington Hotel, 103 E Piccadilly St, ☏ . Check-in: 4PM, check-out: 11AM. Luxury suites with fireplaces and whirlpool tubs. Spa and pool.
- 2 Nancy Shepherd House Inn Bed and Breakfast, 618 S Loudoun St (right downtown on Winchester's main street), ☏ . Great value with a fantastic breakfast. Very interesting historic inn right downtown with excellent restaurants, shops, pubs, coffee houses, and museums all around. Four extremely comfortable & cozy bedrooms, two with fireplaces. $79 - 139.
- 3 L'Auberge Provencale Bed and Breakfast, 13630 Lord Fairfax Hwy, White Post (12 km SE on stare Highway 50), ☏ , toll-free: , email@example.com. Features French cuisine W-Su. $240-470.
- The Shenandoah National Park is about 50 miles south on I-81.
- Skyline Drive runs parallel to I-81 south into Tennessee.
- Washington, D.C.
- Harper's Ferry, Antietam, and Gettysburg are within an easy drive for visiting Civil War Battlefields and learning about the Civil War.
|Routes through Winchester|
|Hagerstown ← Martinsburg ←||N S||→ Middletown → Roanoke|
|END ←||N S||→ Fredericksburg → Norfolk|
|Clarksburg ← Romney ←||W E||→ Middleburg → Washington, D.C.|
|Hancock ← Berkeley Springs ←||N S||→ Front Royal → Jct|
|END ←||W E||→ Berryville → Alexandria|