Winchester 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.

1. Museum of the Shenandoah Valley

Museum of the Shenandoah Valley
© Museum of the Shenandoah Valley

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. Browse our Romantic Weekend Getaways in Virginia guide for more ideas.

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

2. Stonewall Jackson's Headquarters

Stonewall Jackson's Headquarters
© Stonewall Jackson's Headquarters

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, Winchester, Virginia
© Abram's Delight

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

Cedar Creek & Belle Grove National Historical Park
© NPS Photo

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, (website link)

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5. Bright Box Theater

Bright Box Theater
© Bright Box Theater

Since its inception in May 2013, Bright Box Theater has brought the joys of live entertainment to theatre-lovers in the greater Winchester area. Located directly on the Pedestrian Mall in the heart of Winchester, Bright Box Theater is a dynamic entertainment hub, where a wide variety of musical and comedy shows are presented to the public. The facility boasts state-of-the-art lighting and sound equipment which makes it ideal for a variety of shows and concerts including Murder Mystery Dinner Shows and some adult comedy offerings. There is always something interesting on at the Bright Box and visitors are advised to book their tickets online to avoid disappointment.

Bright Box Theatre, 15 N. Loudoun Street, Winchester, VA 22601, 540 665 2878

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6. George Washington's Office Museum

George Washington's Office Museum
© George Washington's Office Museum

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, (website link)

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7. Patsy Cline Historic House

Patsy Cline Historic House
© Patsy Cline Historic House

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

Marker Miller Orchards and Farm Market
© Marker Miller Orchards and Farm Market

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

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9. Rinker Orchards

Rinker Orchards
© 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

Sunflower Cottage & Backroom Brewery
© Sunflower Cottage & Backroom Brewery

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

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11. Dinosaur Land

Dinosaur Land
© 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, (website link)

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12. Family Drive-In Theatre

Family Drive-In Theatre
© 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

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13. Rocking S Ranch

Rocking S Ranch
© 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

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14. Abrams Creek Wetlands Preserve

Abrams Creek Wetlands Preserve
© Courtesy of ETIEN - Fotolia.com

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

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15. Shenandoah Valley Discovery Museum

Shenandoah Valley Discovery Museum
© Shenandoah Valley Discovery Museum

The original Shenandoah Valley Discovery Museum was a modest museum with just 5 exhibits. However, it was so popular with the community that it grew by leaps and bounds and moved into a large new home in 2014. The core mission of the museum is to instill a hunger for knowledge in all visiting children, and the exhibits are designed to encourage young minds to actively engage in interactive learning. Visitors can explore 4 levels of fascinating hands-on exhibits which will delight as they educate. Visitors can host birthday parties at the museum and there are regular Summer Camps for children of all ages.

Shenandoah Valley Discovery Museum, 19 West Cork Street, Winchester, VA 22601, 540 722 2020, (website link)

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16. Things to Do Near Me: Kernstown Battlefield

Things to Do Near Me: Kernstown Battlefield
© Kernstown Battlefield

The Kernstown Battlefield was the site of two decisive historic Civil War battles which took place on a farm belonging to Samuel and Helen Pritchard. The first battle took place in 1862 and the second battle in 1864; by the end of the Valley Campaign in 1864, much of the peaceful Shenandoah Valley had been left in ruins. Today visitors can come and visit the battlefield to learn more about these 2 key battles and the part they played in the Civil War. The Battlefield is open to the public on Saturdays and Sundays from April 23 through October 30th, and on the anniversaries of the 2 key battles. You can walk along interpretive trails and visit the 1854 homestead, museum and shop.

Kernstown Battlefield, 610 Battle Park Drive, Winchester, VA 22601, 540 450 7835

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17. Winchester Ciderworks

Winchester Ciderworks
© Winchester Ciderworks

The Shenandoah Valley is widely known to be home to a large number of apple orchards, so it makes perfect sense that fine ciders should be produced here. Winchester Ciderworks combines old world traditions with modern methods to produce a quality product that all cider lovers will enjoy. You are invited to stop by their rustic tasting room, which occupies a vintage barn which has been used for apple storage and cold storage for decades since it was built in 1900. Winchester Ciderworks presses and ferments all their apples onsite before maturing all their ciders for a least a year. Then they are bottled or canned for your enjoyment. Browse VA beaches

Winchester Ciderworks, 2504 N. Frederick Pike, Winchester, VA 22603, 540 686 7632

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18. Union Jack Pub and Restaurant

Union Jack Pub and Restaurant
© Acker/stock.adobe.com

Located in the former Union Bank Building, which dates back to the Victorian era, the Union Jack Pub and Restaurant exudes old fashioned charm and history. Surrounded by this special ambiance, customers are invited to settle in and enjoy authentic British-style pub grub and a fine choice of around 40 beers on tap, as well as huge selection of European beers, craft beers and wines. They serve a wide selection of delicious meals including their signature fish and chips, which is rumored to be the best in the city. Other popular menu items include a variety of burgers and sliders, salads, flatbreads and much more.

Union Jack Pub and Restaurant, 101 N. Loudoun Street, Winchester, VA 22601, 540 722 2055

19. Violino Ristorante Italiano

Violino Ristorante Italiano
© Violino Ristorante Italiano

Widely acknowledged to be one of the best Italian restaurants in the city, Violino Ristorante proudly serves beautifully prepared authentic Italian cuisine. They hand-make many of their ingredients on-site, including a mouth-watering mozzarella, delicious Italian sausage, and most of their pastas are also house-made. The menu contains all your favorite Italian dishes including antipasti, soups, salads, pastas and delicious veal, beef, poultry and sea food entrees. In summer, the emphasis is definitely on their freshly sourced sea food and fish dishes, all designed to welcome the arrival of warmer Mediterranean style weather – this is when you can feast on Canadian lobster and Lo Scoglio – a decadent medley of mixed sea food on homemade pasta.

Violino Ristorante Italiano, 181 N. Loudoun Street, Winchester, VA 22601, 540 667 8006

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20. Tourist Attractions: Civil War Orientation Center, Winchester, Virginia

Tourist Attractions: Civil War Orientation Center, Winchester, Virginia
© Civil War Orientation Center

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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