20 Best and Fun Things to Do in Winchester Va (Virginia)

Winchester, Virginia, is a small city located in the scenic Shenandoah Valley. Visitors can learn about the city’s history by visiting Old town Winchester, the Glen Burnie Historic House, and the Museum of the Shenandoah Valley. The Stonewall Jackson Headquarters Museum, the Cedar Creek Battlefield, and other antebellum and Civil War-related structures and landmarks are also located in the old town winchester city.

Things to Do in Winchester Va, with its surrounding hills and countryside, provides numerous opportunities to enjoy nature at West Virginia. Hiking, swimming in area lakes, visiting a farm or orchard, and exploring the area on horseback on a trail ride are all options. Call the attractions and restaurants ahead of time to confirm current hours of operation.

20 List of Things to Do in Winchester Va Today

1.Winchester, Virginia’s Shenandoah Valley Museum

The Museum of the Shenandoah Valley is a museum that preserves and interprets the region’s history, art, and culture. The complex includes a main museum building designed by renowned architect Michael Graves, 7 acres of gardens, and an 18th-century historic home. The museum’s permanent collection includes a large number of artifacts, works of art, documents, maps, and other items from the region. There is also a temporary exhibition space with changing exhibits. The historic Glen Burnie Historic House is open for tours and is surrounded by 7 acres of beautiful gardens that welcome visitors as well.

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

2. Stonewall Jackson’s headquarters in Winchester, Virginia.

Stonewall Jackson’s Headquarters is housed in a Hudson River Gothic revival style home that was once General “Stonewall” Thomas Jackson’s winter headquarters in the early 1860s. It is now used as a museum to commemorate the general’s memory and military prowess. Jackson’s office has been preserved almost exactly as it was when he used it. The house houses the world’s largest collection of Stonewall Jackson memorabilia, as well as many personal items from his various staff members. His personal prayer table and a collection of family artifacts are among the most important items in the museum.

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

3. Winchester, Virginia’s Abram’s Delight

Abram’s Delight is a historic home that was built in 1754, making it the city of Winchester’s oldest home. Five generations of the Hollingsworth family owned the house for nearly 200 years. The house is a historic house museum that is representative of the type of homes built by Scotch-Irish settlers in the Shenandoah Valley. The house’s exterior is made of rubble limestone set on a stone foundation and topped with a slate roof. On the west lawn, there is a reconstructed log cabin from 1780. The tour price includes admission to the cabin.

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

4.Winchester, Virginia’s Cedar Creek & Belle Grove National Historical Park

Cedar Creek and Belle Grove National Historical Park was established to protect and preserve several historically and culturally significant locations throughout the Shenandoah Valley region, and it is a must-see for any history buffs in your family. The location of the American Civil War Battle of Cedar Creek is the most significant site in the historical Jim Barnett park at blue ridge parkway. The Belle Grove Plantation is also an important historical site that is open to the public for tours. The park rangers offer a variety of programs for visitors, including historical and cultural programming about the Shenandoah Valley, as well as fascinating looks at the Battle of Cedar Creek and the region’s deep impact from the Civil War.

Phone: 540-869-3051, Middletown, VA

5. Bright Box Theater

Bright Box Theater has brought the joys of live entertainment to theatregoers in the greater Winchester area since its inception in May 2013. Bright Box Theater, located directly on the Pedestrian Mall in the heart of Winchester, is a dynamic entertainment hub where a wide variety of musical and comedy shows are presented to the public. The venue has cutting-edge lighting and sound equipment, making it ideal for a variety of shows and concerts, including Murder Mystery Dinner Shows and adult comedy offerings. The Bright Box always has something interesting going on, and visitors are advised to book their tickets online to avoid disappointment at skyline drive.

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

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

George Washington’s Office is a log cabin museum that houses many of President George Washington’s personal items as well as period artifacts and other historical features in United States. From 1755 to 1756, the president used the log cabin as his military office. The office contains a number of artifacts, including a cannon left behind in Alexandria by General Edward Braddock. There are also several personal items from George Washington on display, as well as a 1755 model of Winchester that includes Fort Loudoun. The museum is open for tours seasonally, has a gift shop, and occasionally hosts special events and exhibitions.

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

7. Winchester, Virginia’s Patsy Cline Historic House

The Patsy Cline House is Virginia Patterson Hensley’s historic home, where she lived from 1948 to 1953. Patsy Cline later became known as and had a successful career as a country music star, and the Greek revival home is now open as a museum dedicated to Cline’s life and career at Mount Hebron Cemetery. She lived in the house for many years while pursuing her dream of becoming a musician at winchester cathedral. The home is only open for tours seasonally, and the tour includes the garden. There is a gift shop on-site where visitors can buy items related to the house, Patsy Cline, and country music in general winchester little theatre.

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

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

Marker Miller Orchards and Farm Market is a family-friendly orchard and market that offers visitors a great way to spend a day in the country. The mountain scenery at road trip provides the ideal setting for a relaxing visit. You can also buy containers and head out into the orchard to pick your own produce, which includes farm-fresh fruits and vegetables. Picnic tables can be found throughout the property. You are welcome to bring your own food, but you can also buy food from their food building if it is open. The market sells a variety of items, including their ever-popular apple cider donuts, fresh-made fudge, and more.

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

9.Winchester, Virginia Attractions: Rinker Orchards

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

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

10.Winchester, Virginia’s Sunflower Cottage & Backroom Brewery

Backroom Brewery is a boutique farm brewery located near Front Royal at the Sunflower Cottage Herb Farm. The brewery specializes in small-batch fresh-brewed beer made from locally grown hops and herbs. The brewery has a tasting room where they serve their own craft beer on tap along with appetizers, sandwiches, and a variety of comfort food dishes. Sunflower Cottage, the herb farm, grows more than 120,000 herb plants each spring, as well as acres of hops used in the brewery’s 20 beer varieties. The farm is especially popular in the fall, when families come to enjoy the farm’s seasonal attractions.

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

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

Dinosaur Land is a quirky dinosaur-themed attraction in White Post with over 50 giant model dinosaurs. Visitors can explore the grounds and imagine life as it might have been during the Mesozoic era, long before humans existed. The family-friendly attraction is ideal for dinosaur enthusiasts and anyone with an interest in the prehistoric era. Although there are no moving parts or high-tech attractions, fans continue to visit and return. Dinosaur Land has a large gift shop with a wide variety of Dinosaur Land and dinosaur-related items that will keep dinosaur fans of all ages entertained.

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

12.Winchester, Virginia Attractions: Family Drive-In Theatre

The Family Drive-In Theatre is a drive-in movie theater located near Stephens City. The theatre first opened its doors in 1956 and has remained a locally owned and operated business ever since. It is now one of Virginia’s last remaining drive-in movie theaters. The theater has two screens and shows first-run movies in a double-feature format. Every night, moviegoers can watch two films for one low price. The theater has many features that will make you nostalgic for old-school drive-in theaters, such as retro music before the show, a playground for children, car speakers, and more. However, the theater employs cutting-edge technology to provide a high-quality movie-watching experience.

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

13.Winchester, Virginia Attractions: Rocking S Ranch

The Rocking S Ranch provides a beautiful setting for city dwellers in Northern Virginia, suburban Maryland, and Washington, D.C. to escape to the country and spend time with horses. The lovely ranch is nestled in the hills of the Shenandoah Valley but is easily accessible from many urban areas. They provide horseback riding lessons for children and adults of all skill levels, as well as trail rides through the foothills, which are popular with area visitors. The trails follow the Shenandoah Valley’s ridgelines and foothills and pass through areas where Confederate and Union troops rode during the Civil War, making them appealing to both adventurers and history buffs.

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

14.Winchester, Virginia Attractions: Abrams Creek Wetlands Preserve

Abrams Creek Wetlands Preserve is a nature preserve with a multi-use trail and the opportunity to enjoy nature and observe wildlife in its natural habitat. The preserve attracts cyclists, joggers, and walkers who come to enjoy the 1-mile trail. The Winchester Green Circle path winds through the wetlands, providing views of numerous bird species and rare plant varieties. During your visit, you may see green and blue herons, kingfishers, turtles, muskrats, and other animals. On occasion, guided walking tours of the nature preserve are available, with an emphasis on the plants and animals that live there.

Winchester, VA 22601 1643 Meadow Branch Avenue

15. Shenandoah Valley Discovery Museum 

The original Shenandoah Valley Discovery Museum featured only five exhibits. However, it became so popular in the community that it expanded rapidly and moved into a large new facility in 2014. The museum’s primary goal is to instill a thirst for knowledge in all visitors, and the exhibits are designed to encourage young minds to actively engage in interactive learning. Visitors can explore four levels of fascinating hands-on exhibits that will both entertain and educate. Birthday parties can be held at the museum, and there are regular Summer Camps for children of all ages.

540 722 2020, Shenandoah Valley Discovery Museum, 19 West Cork Street, Winchester, VA 22601.

16.Kernstown Battlefield

The Kernstown Battlefield was the site of two pivotal historic Civil War battles that took place on Samuel and Helen Pritchard’s farm. The first battle was in 1862, and the second in 1864; by the end of the Valley Campaign in 1864, much of the peaceful Shenandoah Valley had been destroyed. Visitors can now come to the battlefield to learn more about these two pivotal battles and their roles in the Civil War. From April 23 to October 30th, and on the anniversaries of the two key battles, the Battlefield is open to the public on Saturdays and Sundays. You can take interpretive trails and visit the 1854 homestead, museum, and gift shop.

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

17. Winchester Ciderworks 

Because the Shenandoah Valley is known for having a large number of apple orchards, it stands to reason that fine ciders would be produced here. Winchester Ciderworks combines old world traditions with modern methods to create a high-quality product that cider enthusiasts will appreciate. You are welcome to visit their rustic tasting room, which is housed in a vintage barn that has been used for apple storage and cold storage since it was built in 1900. All of Winchester Ciderworks’ apples are pressed and fermented on-site before being aged for at least a year. They are then bottled or canned for your pleasure.

Winchester Ciderworks is located at 2504 N. Frederick Pike, Winchester, VA 22603, and can be reached at 540 686 7632.

18. Union Jack Pub and Restaurant is located on Union Street.

The Union Jack Pub and Restaurant is housed in the former Union Bank Building, which dates back to the Victorian era and exudes old-world charm and history. Customers are invited to settle in and enjoy authentic British-style pub grub and a fine selection of around 40 beers on tap, as well as a huge selection of European beers, craft beers, and wines, surrounded by this special ambiance. They serve a variety of delectable dishes, including their signature fish and chips, which is said to be the best in town. A variety of burgers and sliders, salads, flatbreads, and other menu items are also popular.

101 N. Loudoun Street, Winchester, VA 22601, 540 722 2055.

19. Ristorante Italiano Violino

Violino Ristorante, widely regarded as one of the best Italian restaurants in town, proudly serves beautifully prepared authentic Italian cuisine. Many of their ingredients are handcrafted on-site, including mouthwatering mozzarella and delectable Italian sausage, and the majority of their pastas are also made in-house. All of your favorite Italian dishes are available, including antipasti, soups, salads, pastas, and delectable veal, beef, poultry, and seafood entrees. The emphasis in the summer is unmistakably 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.

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

20.Winchester, Virginia Civil War Orientation Center

The Winchester-Frederick Visitors Center includes the Civil War Orientation Center. The center’s highlight is an interactive touchscreen that allows you to virtually explore the various Civil War sites in the area before visiting them in person. The center is an excellent starting point for exploring Winchester’s and the surrounding area’s rich Civil War history. In addition to the Civil War Orientation Center, the visitors center has knowledgeable travel counselors who can help you make reservations, provide directions, and more. There are also brochures, souvenirs, and maps available.

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

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