Winchester's Main Square

Winchester is a town in the Shenandoah Valley. The town is a good base for exploring the rest of the valley and a picturesque historical site in its own right. It was the first colonial town in the Valley. It has a wonderful historic district with a nice pedestrian mall. The town is full of excellent restaurants, shops and museums. There is one very old inn downtown with a pineapple sign hanging on the porch, plus there is the restored George Washington Hotel.

Understand

It was home to 28,000 people in 2020.

George Washington spent much of his time in Winchester. The town was important during the French and Indian War, the Revolution, and Civil War. Winchester was also home to country music legend Patsy Cline.

Get in

Winchester is located just off of Interstate 81. Winchester is a 1-hour 15-minute drive (75 miles, 120 km) from Washington, D.C., and a 1-hour 45-minute drive (100 miles, 160 km) from Baltimore.

The closest airport with scheduled commercial service is Washington Dulles International Airport (IAD ^IATA), 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.

Get around

The historical downtown can be seen on foot, but a car will allow you to explore the nearby Shenandoah National Park and scenic Skyline Drive .

• 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.

See

• 1 Stonewall Jackson's Headquarters, 415 N. Braddock St., ☏ +1 540 667-5505.  
• 2 Handley Library (Handley Regional Library), 100 W. Piccadilly Street (Corner of Rt. 7 and Rt. 11), ☏ +1 540 662-9041. 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. (updated Sep 2019)
• 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. (updated Sep 2019)
• 5 George Washington's Office (Adam Kurtz House).  
• 6 Shenandoah Valley Discovery Museum, 19 W Cork St, Winchester (Route 50), ☏ +1 540 722 2020. W-Sa 9:30AM–3:30PM, and Su 12:30–3:30PM in the winter. Interactive, hands-on museum for families, which focuses on the science, mathematics, humanities and the arts. $9 per person ages 2 and up, children under age 2 are free. (updated Jan 2024)
• 7 Mount Hebron Cemetery. Historic cemetery (updated Sep 2019)
  • 8 Winchester National Cemetery. The Union cemetery within Mount Hebron (updated Sep 2019)
  • 9 Stonewall Cemetery. The Confederate cemetery within Mount Hebron (updated Sep 2019)
• 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. (updated Sep 2019)
• 11 Museum of the Shenandoah Valley. Local history and art museum. (updated Sep 2019)
  • 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. (updated Sep 2019)
• 13 Shenandoah University. (updated Sep 2019)
• 14 Fort Collier. Largely intact Confederate fort (updated Sep 2019)
• 15 Star Fort. Earthwork star fort involved in the Second and Third Battles of Winchester. Free. (updated Sep 2019)
• 16 Marker-Miller Orchards, 3035 Cedar Creek Grade (Route 622) (15 minutes (7 miles, 11 km) west of the city), ☏ +1 540 662-1391. Open July-December. Pick-your-own apples. Buy fruit, vegetables, and baked items. 

Do

A cannon used by George Washington in 1755 in downtown Winchester

• 1 Shenandoah Apple Blossom Festival, Winchester. Held each spring, usually in late April or early May, this festival includes carnivals, pageants, parades, and a circus as part of the celebrations. (updated Jun 2021)
• 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, ☏ +1 540 542-1326. May–Oct, 1st and 3rd Fridays at 6PM and 2nd and 4th Sundays at 4PM. $10. (updated Jan 2023)
• 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. 

Buy

• 1 Bell's Fine Clothing, 122 N Loudoun St, ☏ +1 540 667-1430. M-F 9:30AM-6PM, Sa 9:30AM-5PM, closed Su. Formal clothing. (updated Jan 2023)
• 2 Handworks, 150 N Loudoun St, ☏ +1 540 662-3927. M-Th 10AM-6PM, F Sa 10AM-9PM, Su 11AM-5PM. Home goods. (updated Jan 2023)
• 3 Kimberly's, 135 N Braddock St, ☏ +1 540 662-2195. M-Sa 10AM-6PM, Su 11AM-5PM. Boutique with clothing and gifts. (updated Jan 2023)

Eat

• 1 Snow White Grill, 159 N Loudoun St (Along the central pedestrian walkway), ☏ +1 540 662-5955. 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), ☏ +1 540 667-3777. American food including ribs. Outdoor seating during summer. 

Drink

• 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, ☏ +1 540 667-2743. Tu-Th 4PM-9PM, F 4-10PM, Sa noon-10PM, Su noon-9PM, closed M. Brewery serving wood-fired pizza. (updated Jan 2023)

Sleep

• 1 George Washington Hotel, 103 E Piccadilly St, ☏ +1 540 431-2498. 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), ☏ +1 540-247-5073. 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), ☏ +1 540 837-1375, toll-free: +1-800-638-1702, celebrate@laubergeprovencale.com. Features French cuisine W-Su. $240-470. (updated Oct 2021)

Go next

• 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