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- 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), ☏ . 10-8 (M-W) and 10-5 (Th-S). 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 9-5; Sunday 1-5. 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.
- Marker-Miller Orchards. Open July-December. Route 622.
- 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.
- Civil War Walking Tour. Educational 1 1/2 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.
- Many products related to apples.
- 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.
- Cork Street Tavern, 8 West Cork Street (In old town Winchester), ☏ . American food including ribs. Outdoor seating during summer.
- [dead link] Tater Hill Tavern, 618 South Loudoun Street (inside the Nancy Shepherd House Inn), ☏ . by appointment only. This amazing ancient tavern ale and wine room is inside the Nancy Shepherd House Inn. If you like historic early taverns, this one is a must see while visiting Winchester, but you must be an overnight guest of the Inn for the privilege...or if you are not an overnight guest, you might try your luck and call to see if the innkeepers will invite you in anyway. It's worth a try.
- Old Waterstreet Inn - 19th century house. Some rooms with fireplace; breakfast and cocktails included. $120-155.
- George Washington Hotel - Luxury suites with fireplaces and whirlpool tubs. Spa and pool.
- Long Hill Bed & Breakfast. #1 inn in the South. Custom 10,000 sq.ft. house on 20 A. Savor an award winning family style gourmet breakfast. View birds & wildlife. Great getaway; vacation anchor. Shoot pool; work puzzles; Good food, good rest; feel like family when you leave.
- Nancy Shepherd House Inn Bed and Breakfast, 618 South Loudoun Street Winchester VA 22601 (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.
- 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|