Winchester, Virginia: A Visitors Guide

Old Town Winchester
Photo © Rachel Cooper, licensed to, Inc.

Winchester is a small town located in the Shenandoah Valley region of Virginia with charming shops, unique restaurants, historic architecture and landmarks and a wide variety of recreation opportunities within an easy drive. Old Town Winchester is the artistic hub of the region with concerts, plays, operas and other cultural events throughout the year. This area is fun to explore and makes an easy day trip or weekend getaway from Washington DC.

Getting There

Winchester is located in the Northern Shenandoah Valley, just 72 miles northwest of Washington DC and 22 miles north of Shenandoah National Park. From Washington, DC: Take Route 66 West to I-81 North, Exit 313 or Take VA-267 W (The Dulles Toll Road) to VA-7 W at exit 1A, continue on VA-7 to Winchester.

Notable History

Winchester played an important role in George Washington’s life as his military and political career began there. Washington visited Frederick County, Virginia at the age of sixteen to survey the lands of Thomas, the Sixth lord Fairfax. In 1756, he supervised the construction of Fort Loudoun, the fort that served as the command center for the VA Regiment during the French and Indian War. He was elected to his first public office as the county’s representative to the House of Burgesses.

Winchester and Frederick County was the scene of six battles during the Civil War, and the city itself changed flags around seventy times during the four year conflict.

General Thomas “Stonewall” Jackson demonstrated his military leadership in the Valley Campaign. Jackson set up his headquarters from a home in Old Town Winchester during the winter of 1861-1862.

Old Town Winchester

Founded in 1744 by Colonel James Wood, Winchester is the oldest city in the Commonwealth of Virginia west of the Blue Ridge Mountains.

The historic district has many beautifully restored Federalist style structures and is an interesting place to explore. The heart of town is the Loudoun Street Walking Mall, a four block pedestrian only area bordered by Washington, Fairfax, Clifford and Kent Streets.

Visiting Tips

  • Stop by the Winchester-Frederick County Visitor Center, located at 1400 S. Pleasant Valley Rd., to find maps and brochures and watch an orientation film.
  • Purchase a block ticket for admission to Abram’s Delight Museum, Stonewall Jackson’s Headquarters Museum and George Washington’s Office Museum. The guides at all of the museums are very knowledgeable and friendly. The tours are short and you can easily visit all three attractions in one day. Note that the museums close at 4 p.m., so plan accordingly.
  • Take time to stroll through Old Town Winchester and appreciate the historic architecture. Enjoy a relaxing meal at one of the town’s restaurants. There’s a variety of cuisine ranging from casual fare to fine dining.
  • Take a peek inside the Handley Regional Library and marvel over the beautiful architecture of the historic building.
  • Visit the Museum of the Shenandoah Valley, located just outside of town and be sure to explore the gardens of the Glen Burnie Historic House.
  • Attend one of the town’s many festivals or cultural events (see a list of major events listed below)
  • Take a drive and visit many of the popular attractions in the surrounding areas of Frederick County, Virginia.

Major Attractions in Winchester

The Museum of the Shenandoah Valley - 901 Amherst Street. Located just outside of Old Town, the museum interprets the art, history, and culture of the Shenandoah Valley. The museum complex also includes Glen Burnie Historic House and six acres of spectacular gardens.

George Washington's Office Museum - 32 West Cork and Braddock. George Washington used this small log building in Winchester as a military office while Fort Loudoun was being constructed at the north end of town. The building now serves as a museum and tells the story of how Washington planned Fort Loudoun and displays some of his personal items, surveying equipment and a model of Winchester circa 1755.

Stonewall Jackson's Headquarters Museum - 415 N. Braddock Street. This historic home was used as headquarters by General Thomas Jonathan "Stonewall" Jackson during the winter of 1861-1862. The house contains the largest collection of Jackson memorabilia and personal objects from members of his staff.

Old Court House Civil War Museum - 20 N. Loudoun Street. This Georgian style 1840 Court House maintains a nationally recognized collection of Civil War artifacts and provides tours of the building. The building was used as a hospital and a prison during the Civil War.

Handley Regional Library – 100 W. Piccadilly St. The Beaux-Arts style building is an architectural marvel. Judge John Handley of Scranton, Pennsylvania left $250,000 in his will to build the public library for the people of the city of Winchester. The Stewart Bell Jr. Archives, located in the basement of the library, houses an extensive collection of materials on the people, places, and events of lower Shenandoah Valley from 1732 to present.

The Winchester Little Theatre – 315 W Boscawen St. Dating back to 1929, the theater serves as a venue for community entertainment and culture.

Bright Box Theater - 15 N. Loudoun St. Bright Box is Winchester's premiere performance and events venue with state-of-the-art sound, lighting, and projection equipment. Bright Box provides a dynamic space for concerts, comedy, film screenings, art shows, private parties, fundraisers, and other events.

Patsy Cline Historic House - 608 S Kent St, Winchester, VA. The landmark is on the National Register of Historic Places. Singer Patsy Cline resided here from 1948-57. A 45-minute tour is offered April-October.

Shenandoah Valley Discovery Museum – 54 S Loudoun St, Winchester, VA. The children’s museum provides a variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts.

Additional Nearby Attractions

Belle Grove Plantation - 336 Belle Grove Rd Middletown, VA. Situated on 283 acres, the 1797 Manor House was built by Major Isaac Hite and his wife Nelly Madison Hite, sister of President James Madison and offers breathtaking mountain views of the Shenandoah Valley. Visitors can explore the Manor House, 1815 icehouse and smokehouse, garden, slave cemetery, and apple orchard.

Dinosaur Land - 3848 Stonewall Jackson Highway White Post, VA. The attraction features more than 50 dinosaurs, inviting visitors to step into the world of the prehistoric past when dinosaurs were the only creatures that roamed the earth.

Cedar Creek and Belle Grove National Historical Park – 7712 Main Street Middletown, VA. The 3,500-acre historic site offers free programs and exhibits covering the history of the Shenandoah Valley, the Civil War and Battle of Cedar Creek.

Historic Long Branch - 830 Long Branch Millwood, VA. The 18th century Greek Revival Mansion is exquisitely restored and furnished with period antiques. The house and gardens are the home of the Shenandoah Valley Wine and Music Festival.

Annual Events

Shenandoah Apple Blossom Festival - May
Bluemont Concert Series - June-August
Rockin Independence Eve - July
Frederick County Fair - July/August
Civil War Weekend - August
Apple Harvest Arts & Crafts Festival – September
Downtown Tailgate - September
Octobeer Fest – October
Re-enactment of the Battle of Cedar Creek - October
First Night Winchester – December 31

For information about accommodations, dining, tours and more, visit the website for the Winchester-Frederick County Convention & Visitors Bureau