15 Best Things to Do in Winchester, Virginia

By VI Staff on October 11, 2021 - Updated

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Winchester, Virginia, is a small city set in the beautiful hills of the Shenandoah Valley. The city has a long history, which one can learn about by visiting Old Winchester, the Glen Burnie House, and the Museum of the Shenandoah Valley. The city is also home to the Stonewall Jackson’s Headquarters Museum, the Cedar Creek Battlefield, and other antebellum and Civil War-related structures and landmarks. With hills and countryside all around, Winchester also offers plenty of opportunities to enjoy nature. You can choose from opportunities to hike, swim in area lakes, visit a farm or orchard, and explore the area on horseback on a trail ride. Certain attractions may be temporarily closed or require advance reservations. Some restaurants are currently offering pickup only. Hours/availability may have changed.

1.Museum of the Shenandoah Valley, Winchester, Virginia

The Museum of the Shenandoah Valley is a museum that preserves and interprets the history, art, and culture of the Shenandoah Valley region. The complex contains a main museum building, which was designed by renowned architect Michael Graves, 7 acres of gardens, and a historic home from the 18th century. The museum has several galleries with a large number of artifacts, pieces of art, documents, maps, and more from the region in the permanent collection. There is also temporary exhibition space where changing exhibits are displayed. The historic Glen Burnie Home is available for touring and is surrounded by 7 acres of beautiful gardens, which also welcome visitors.

901 Amherst Street, Winchester, VA 22601, Phone: 888-556-5799

2.Stonewall Jackson's Headquarters, Winchester, VA

Stonewall Jackson’s Headquarters occupies a Hudson River Gothic revival style home that was formerly used as the headquarters of General “Stonewall” Thomas Jackson for winter in the early 1860s. It is now operated as a museum to honor the general’s memory and his military skill. Jackson’s office is preserved in virtually the same state it was in when he used it. The home has the largest existing collection of Stonewall Jackson memorabilia and also features many personal objects from his various staff members. Some of the museum’s most significant items include his personal prayer table and a collection of family artifacts.

415 North Braddock Street, Winchester, VA 22601, Phone: 540-667-5505

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3.Abram's Delight, Winchester, Virginia

Abram’s Delight is a historic home that was built in 1754, making it the oldest home in the city of Winchester. For nearly 200 years, the home was owned by five generations of the Hollingsworth family. The home is representative of the type of homes built by Scotch-Irish settlers in the Shenandoah Valley and today is operated as a historic house museum. The exterior of the home is made from rubble limestone set on a stone foundation and covered with a slate roof. There is a reconstructed log cabin on the west lawn, which dates to 1780. Entrance to the cabin is included with the tour price.

1340 S. Pleasant Valley Road, Winchester, VA 22601, Phone: 540-662-6519

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4.Cedar Creek & Belle Grove National Historical Park, Winchester, VA

Cedar Creek and Belle Grove National Historical Park was created in order to protect and preserve several historically and culturally significant locations throughout the Shenandoah Valley region and it is the perfect stop to put on your list for any history buffs in your family. The most significant site in the historical park is the location of the American Civil War Battle of Cedar Creek. The Belle Grove Plantation is also a significant site and is open to the public for touring. The park rangers offer a number of programs for visitors, which include historical and cultural programming related to the Shenandoah Valley as well as interesting looks at the Battle of Cedar Creek and the deep impact that the Civil War had on the region.

Middletown, VA, Phone: 540-869-3051

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5.Civil War Orientation Center, Winchester, Virginia

The Civil War Orientation Center is part of the Winchester-Frederick Visitors Center. The highlight of the center is an interactive touchscreen where you can virtually explore the various Civil War sites in the area before you head out to see them in person. The center is the perfect jumping off point for exploring the rich Civil War history of Winchester and the surrounding area. In addition to the Civil War Orientation Center, the visitors center has helpful travel counselors who are knowledgeable of the area and can help you make reservations, provide directions, and more. Brochures, souvenirs, and maps are all available as well.

1400 S. Pleasant Valley Road, Winchester, VA 22601, Phone: 540-542-1326

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6.George Washington's Office Museum, Winchester, Virginia

George Washington’s Office is a museum housed within a log cabin and holds many of President George Washington’s personal items as well as period artifacts and other historical features. The president used the log cabin as his military office from 1755 to 1756. There are a number of artifacts displayed in the office, including a cannon that was left behind in Alexandria by General Edward Braddock. There are also several personal items from George Washington, exhibited alongside a model of Winchester from 1755, which includes Fort Loudoun. The museum is open seasonally for touring and features a gift shop and occasionally hosts special events and exhibitions.

32 W. Cork Street, Winchester, VA 22601, Phone: 540-662-4412

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7.Patsy Cline Historic House, Winchester, Virginia

The Patsy Cline House is the historic home of Virginia Patterson Hensley, who lived in the home from 1948 to 1953. She later became known as Patsy Cline and had a successful career as a country music star, and the Greek revival home is open as a museum home dedicated to Cline’s life and career. The home was her residence during many of the years she was pursuing her dream to be a musician. The home is only open seasonally for touring, and the tour includes the garden. There is an on-site gift shop where visitors can purchase items related to the home, Patsy Cline, and country music in general.

608 S. Kent Street, Winchester, VA 22601, Phone: 540-662-5555

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8.Marker Miller Orchards and Farm Market, Winchester, Virginia

Marker Miller Orchards and Farm Market is a family-friendly orchard and market that provides a great way for visitors to experience a day out in the country. The mountain scenery offers the perfect backdrop for a relaxing visit. You can also purchase containers and go out into the orchard to pick your own produce, including both farm-fresh fruits and vegetables. There are picnic tables located throughout the property. You are welcome to bring your own meal but can certainly purchase food from their food building, if it is open. The market offers a number of products to choose from, including their ever-popular apple cider donuts, fresh-made fudge, and more.

3035 Cedar Creek Grade, Winchester, VA 22602, Phone: 540-662-1391

9.Things to Do in Winchester, Virginia: Rinker Orchards

Rinker Orchards is an apple orchard that has been family owned for three generations. The orchards were the family farm of Jacob Dudley Rinker and his wife Emma Glaize, where they grew crops, had an orchard, and raised livestock. Over the years the property became less of a farm operation and more of an orchard and was one of the state’s first pick-your-own apple orchards. Since 1973, the orchard has offered locals and visitors the opportunity to learn about Virginia apples and come out to the country and pick their own fresh apples. They also make their own apple cider, made from 100% Rinker Orchards apples.

1156 Marlboro Road, Stephens City, VA 22655, Phone: 540-869-1499

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10.Sunflower Cottage & Backroom Brewery, Winchester, Virginia

Backroom Brewery is a boutique farm brewery located at the Sunflower Cottage Herb Farm near the town of Front Royal. The brewery specializes in fresh-brewed beer made in small batches from local, farm-grown hops and other herbs. The brewery offers a tasting room, which serves their own craft beer on tap as well as appetizers, sandwiches, and a variety of comfort food dishes. The herb farm, called Sunflower Cottage, grows more than 120,000 herb plants each spring as well as acres of hops used in the brewery’s 20 varieties of beer. The farm is especially busy in the fall, when families flock to the farm to enjoy seasonal attractions.

150 Ridgemont Road, Middletown, VA 22645, Phone: 540-869-8482

11.Things to Do in Winchester, Virginia: Dinosaur Land

Dinosaur Land is an offbeat dinosaur-themed attraction in White Post, featuring more than 50 giant model dinosaurs. Visitors explore the grounds and experience life as it might have been in the Mesozoic era, long before humans roamed the Earth. The family-friendly attraction is perfect for dinosaur fans and anyone interested in the prehistoric era. There are no moving parts or high-tech attractions, but fans continue to visit and return over and over again. Dinosaur Land has a huge gift shop with a large selection of Dinosaur Land and dinosaur-related items, which are sure to keep dinosaur-lovers of any age entertained.

3848 Stonewall Jackson Hwy., White Post, VA 22663, Phone: 540-869-2222

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12.Things to Do in Winchester, Virginia: Family Drive-In Theatre

The Family Drive-In Theatre is an outdoor, drive-in movie theatre near Stephens City. The theatre was opened in 1956 and since then has been a locally owned, family-operated business. Today, it is one of the last remaining drive-in movie theaters in Virginia. The theater has two screens, where they run first-run movies on a double-feature policy. Moviegoers have the opportunity to watch two movies each night for one affordable price. There are many features at the theater that will make you nostalgic for old-school drive-in theaters, such as retro music before the show, a playground for kids, car speakers, and more. However, the theater uses modern technology to ensure a quality movie-watching experience.

5890 Valley Pike, Stephens City, VA 22655, Phone: 540-665-6982

13.Things to Do in Winchester, Virginia: Rocking S Ranch

The Rocking S Ranch offers a gorgeous place for city residents of Northern Virginia, suburban Maryland, and Washington, D.C., to get out in the country and spend time with horses. The beautiful ranch is tucked away in the hills of the Shenandoah Valley but is conveniently accessible from many urban areas. They offer horseback riding lessons for children and adults of all skill levels in addition to trail rides through the foothills, which are quite popular with visitors to the area. The trails follow the ridgelines and foothills of the Shenandoah Valley and traverse areas where Confederate and Union troops rode during the Civil War, so they are interesting for both adventure lovers and history buffs.

564 Glaize Orchard Road, Winchester, VA 22603, Phone: 540-678-8501

14.Things to Do in Winchester, Virginia: Abrams Creek Wetlands Preserve

Abrams Creek Wetlands Preserve is a protected outdoor area offering a multi-use trail and the opportunity to enjoy nature and observe wildlife in its natural habitat. The preserve is popular among cyclists, joggers, and walkers, who come to enjoy the pleasant 1-mile trail. The Winchester Green Circle travels through the wetlands and offers opportunities to see many species of birds and several varieties of rare plants. You may encounter green and blue herons, kingfishers, turtles, muskrats, and other animals during your visit. On some occasions, guided walking tours of the nature preserve are available with a focus on plants and animals that reside in the area.

1643 Meadow Branch Avenue, Winchester, VA 22601