Winchester, Virginia, is a charming city rich in history and variety of activities for visitors to enjoy. From museums to outdoor adventures, there’s something for everyone in this beautiful city. Discover the best of Winchester VA with these must-visit activities:

Key Takeaways:

  • Winchester VA has a rich history to explore.
  • The Shenandoah Valley Discovery Museum offers hands-on exhibits for children.
  • Visiting the Abrams Delight provides a glimpse into 18th-century life.
  • The Shenandoah Valley Civil War Museum showcases Winchester’s role in this significant period of American history.
  • The Shenandoah Valley Wine Trail is a collection of wineries offering tastings and tours.
  • The beautiful Blue Ridge Mountains offer outdoor recreational opportunities.
  • Winchester Brew Works is a local brewery with unique and flavorful beers.

Visit the Shenandoah Valley Discovery Museum

Located in downtown Winchester, the Shenandoah Valley Discovery Museum is a popular attraction for families and children of all ages. The museum features a hands-on approach to education, with interactive exhibits that cover a wide range of topics, including science, technology, engineering, art, and math.

Visitors can explore the museum’s many exhibits, which offer a fun and educational experience. From building with blocks to experimenting with water and light, there is something for everyone to enjoy. The museum’s Discovery Zone is a highlight of the museum, where children can engage in imaginative play and learn about nature. The Discovery Zone features a treehouse, a mini-golf course, and a butterfly garden, among other attractions.

The museum also hosts special events and workshops throughout the year, providing visitors with even more opportunities to learn and have fun. These events range from art classes to science experiments, making the museum a unique destination for all.

For those interested in STEM education or looking for a fun family outing, a visit to the Shenandoah Valley Discovery Museum is a must. The museum offers a chance to explore, discover, and engage in hands-on learning, making it one of the top attractions in Winchester, VA.

Explore the Museum of the Shenandoah Valley

For those interested in art and history, the Museum of the Shenandoah Valley is another must-visit attraction in Winchester. This museum is located in the heart of Winchester, Virginia and offers a comprehensive look at the cultural heritage of the region.

The collection at the Museum of the Shenandoah Valley includes art, decorative arts, and historical objects that date back to the 18th century. Visitors can explore exhibits that showcase the history and development of the Shenandoah Valley, including the impact of the Civil War and the settlement of the region.

A highlight of the museum is the Glen Burnie House and Gardens, a beautifully restored historic home located on the museum’s grounds. Visitors can tour the house, which has been furnished to reflect the lifestyle of a prominent Valley family, and explore the stunning gardens that surround it.

In addition to its permanent collection, the museum also hosts rotating exhibits that showcase contemporary art and delve deeper into the cultural identity of the Shenandoah Valley. The museum also provides a variety of educational programs and events for visitors of all ages, such as hands-on activities, guided tours, and lectures on various topics.

If you are looking to immerse yourself in the rich cultural heritage of the Shenandoah Valley, the Museum of the Shenandoah Valley is a destination not to be missed. Its diverse collection, stunning gardens, and engaging educational programs make it a must-visit attraction for both locals and tourists alike.

Discover the history at Stonewall Jackson’s Headquarters Museum

Winchester played a significant role in the American Civil War, and one place that showcases this history is Stonewall Jackson’s Headquarters Museum, located in Winchester, Virginia. The museum is dedicated to preserving and showcasing the life and legacy of General Thomas J. “Stonewall” Jackson, a well-known military leader.

Housed in the actual building where Stonewall Jackson resided during the Confederate occupation of Winchester, the museum offers visitors a unique opportunity to step back in time and explore the life and times of this great man.

While visiting, you can expect to see a wide range of exhibits that highlight Stonewall Jackson’s military campaigns, personal artifacts, and significant contributions to the Civil War. The displays feature a diverse collection of authentic Civil War artifacts, including weapons, uniforms, maps, and personal items belonging to both Union and Confederate soldiers.

One of the highlights of the museum is the preserved room where Stonewall Jackson planned many of his military strategies. This room has been meticulously restored to its original appearance, allowing visitors to experience firsthand the ambiance of the time.

In addition to the exhibits, the museum offers guided tours led by knowledgeable docents who provide detailed insights into the life and times of Stonewall Jackson. These tours offer a deeper understanding of the historical significance of the museum and its relevance to the Civil War.

Stonewall Jackson’s Headquarters Museum also hosts special events and educational programs throughout the year. These events include lectures, reenactments, and living history demonstrations, providing visitors with a chance to engage in interactive learning experiences.

Whether you are a history enthusiast, a Civil War buff, or simply curious about the life of Stonewall Jackson, a visit to Stonewall Jackson’s Headquarters Museum is a must. Immerse yourself in the rich history and gain a deeper appreciation for one of the most influential figures of the American Civil War.

Enjoy outdoor activities at Jim Barnett Park

If you’re looking to immerse yourself in nature and outdoor activities, Jim Barnett Park is the place to go. The park offers a wide range of recreational options for individuals and families to enjoy. With its beautiful natural setting and well-maintained facilities, it is the perfect place to spend quality time outdoors.

One of the main attractions at Jim Barnett Park is its extensive trail system. Walking, jogging, or biking along the trails provides a great opportunity to exercise while enjoying the beauty of the park. The trails wind through lush greenery, allowing visitors to connect with nature and escape the hustle and bustle of everyday life.

For sports enthusiasts, there are various sports fields and courts available for use. Tennis courts, basketball courts, and baseball fields provide opportunities for friendly matches and recreational play. Whether you prefer a game of tennis or shooting hoops, Jim Barnett Park has the facilities to accommodate your favorite sports.

Families will love the playgrounds scattered throughout the park. These playgrounds are designed to keep children entertained and active, with slides, swings, and climbing structures. Parents can relax on nearby benches while their kids enjoy the play areas.

Additionally, the park features picnic areas and shelters, perfect for enjoying a meal with family and friends. Pack a picnic basket and spend a day in the great outdoors, surrounded by the park’s natural beauty. There are also grills available for those who want to have a barbecue while enjoying the fresh air.

Jim Barnett Park hosts various events and activities throughout the year. From festivals and concerts to sports tournaments and community gatherings, there is always something happening at the park. Check the park’s website or local event listings to stay updated on upcoming happenings.

Overall, Jim Barnett Park offers a wonderful outdoor experience for individuals and families alike. Whether you’re looking to exercise, play sports, have a picnic, or simply enjoy the outdoors, this park has something to offer everyone. So, grab your sneakers, pack a lunch, and head to Jim Barnett Park for a day full of outdoor activities and fun.

Take a scenic drive on the Skyline Drive

For breathtaking views of the surrounding Shenandoah Valley and Blue Ridge Mountains, a scenic drive along the Skyline Drive is a must-do activity. Designated as a National Scenic Byway, Skyline Drive stretches for 105 miles through the heart of Shenandoah National Park, offering unparalleled views of the natural beauty that Virginia has to offer.

The drive winds through the mountains, providing stunning panoramas at every turn. Along the way, visitors can pull over at numerous overlooks to take a break and admire the scenic vistas. These overlooks offer spectacular views of the surrounding landscapes and are perfect for taking memorable photos to cherish for years to come.

One of the best times to embark on a drive along Skyline Drive is during the fall season, when the foliage bursts into a riot of colors. The vibrant reds, oranges, and yellows of the changing leaves create a picturesque backdrop that is a feast for the eyes. However, the drive is equally enchanting during spring and summer, with wildflowers blooming and the lush greenery stretching as far as the eye can see.

To fully experience the park’s natural wonders, visitors should plan ahead and allow ample time for stops at the various overlooks and points of interest along the way. There are also numerous hiking trails that branch off from Skyline Drive, allowing visitors to explore the park on foot and discover hidden gems.

While driving through the park, keep an eye out for the diverse wildlife that calls Shenandoah National Park home. From white-tailed deer and black bears to wild turkeys and squirrels, the park is teeming with animal life. Wildlife sightings add an extra element of excitement to your drive and make for unforgettable memories.

It’s important to note that Skyline Drive has a speed limit of 35 miles per hour, allowing visitors to leisurely enjoy the scenery and take in the natural wonders around them. Additionally, there are entrance fees to access the park, which help support the preservation and maintenance of this natural treasure.

In conclusion, taking a scenic drive on the Skyline Drive is an activity that should not be missed. Whether you visit during the fall foliage season or any other time of the year, you can expect to be captivated by the breathtaking beauty of this iconic road and the surrounding Shenandoah National Park. So, pack a picnic, hop in your car, and get ready to embark on a memorable journey through nature’s masterpiece.

Immerse yourself in history at Cedar Creek and Belle Grove National Historical Park

Located just outside of Winchester, the Cedar Creek and Belle Grove National Historical Park commemorates the site of the American Civil War Battle of Cedar Creek. This park offers visitors a unique opportunity to experience the rich history of the region, including the battlefield and the historic plantation.

The Battle of Cedar Creek was a significant event during the American Civil War and the park offers a number of interpretive signs and walking trails to explore the battlefield and learn about the events that unfolded there. At the Visitors Center, visitors can watch a short film about the battle and browse exhibits that provide further insight into the conflict.

Belle Grove, located within the park, is a historic plantation that served as a headquarters for Union General Philip Sheridan during the battle and was later occupied by Confederate forces. Today, the plantation has been restored and is open for guided tours. Visitors can explore the beautiful gardens, discover the original furnishings, and learn about the daily lives of the plantation’s residents.

In addition to the battlefield and plantation, Cedar Creek and Belle Grove National Historical Park offers a range of recreational activities. Nature enthusiasts can hike on the park’s scenic trails and spot the local wildlife. The park also hosts events and reenactments throughout the year, allowing visitors to witness the history of the area come to life.

Whether you’re a history buff, nature lover, or simply looking for a unique and educational experience, Cedar Creek and Belle Grove National Historical Park is a must-visit destination. Immerse yourself in the storied past of this significant location and gain a deeper understanding of the events that shaped our nation.

Discover the local wineries

Winchester is situated in the heart of Virginia’s wine country, making it the perfect destination for wine enthusiasts. Discovering local wineries in your area is a delightful journey of wine tasting and exploration. Local wineries offer a unique opportunity to experience the flavors and offerings of the region, allowing you to indulge in a memorable wine tasting experience.

When it comes to discovering local wineries, it is important to conduct thorough research. Start by consulting online directories and websites dedicated to promoting and showcasing these wineries. These platforms provide a wealth of information about the wineries’ locations, operating hours, and the types of wines they produce.

Consider exploring wine regions near you. Many areas are known for their vineyards and wineries, offering picturesque landscapes and rich wine heritage. Whether it’s the rolling vineyards of California’s Napa Valley, the serene beauty of the Pacific Northwest’s Willamette Valley, or the charming wineries of the Finger Lakes region in New York, each location has its own unique charm and wine offerings.

Planning a visit to a local winery can be an enriching experience. Most wineries offer guided tours where you can learn about the wine-making process, stroll through the vineyards, and witness the craftsmanship that goes into creating each bottle. Additionally, you can participate in wine tastings, where expert sommeliers guide you through the different varietals, teaching you about the characteristics and flavors that define each wine.

Many local wineries also host special events and festivals throughout the year, creating a festive atmosphere for visitors. These events often feature live music, food pairings, and the opportunity to meet and interact with winemakers themselves. Keep an eye out for these events in your area, as they provide a unique chance to immerse yourself in the local wine culture and connect with other wine enthusiasts.

Supporting local wineries not only allows you to discover hidden gems in your area, but also promotes sustainable agriculture and the local economy. By purchasing wine directly from these wineries, you are supporting the passion and dedication of local winemakers and encouraging the growth of the wine industry in your region.

In conclusion, discovering local wineries is an exciting opportunity to explore the world of wine, taste unique flavors, and immerse yourself in the culture and history of your area. With thorough research, planning, and an open palate, you can embark on a memorable journey of wine discovery right in your own backyard. So, grab a glass and start exploring the local wineries near you. Cheers to a wine-filled adventure!

Browse the downtown area

Winchester’s downtown area is full of charm and character, with its historic buildings, eclectic shops, and inviting eateries. Whether you’re a local resident or a traveler exploring a new city, downtown areas offer a vibrant atmosphere, diverse shops, and exciting entertainment options.

One of the main attractions of browsing the downtown area is the wide range of shopping opportunities. From boutique stores to well-known retail chains, downtown areas are often a haven for shoppers looking for unique and stylish items. Many downtown areas also feature local artisans and craftsmen, offering one-of-a-kind handmade goods that can’t be found anywhere else.

Aside from shopping, strolling through the downtown area allows you to experience the local culture and history of the city. Many downtown areas are filled with historic buildings, architectural wonders, and landmarks that tell stories of a city’s past. Take the opportunity to learn more about the city’s heritage by exploring museums, art galleries, and historical sites dotted throughout downtown.

Additionally, downtown areas are known for their vibrant food scenes. Whether you’re looking for a quick bite or a gourmet dining experience, downtown areas often host a wide variety of eateries, ranging from street food vendors to high-end restaurants. Local cuisine, international flavors, and fusion dishes can all be found within the eclectic mix of dining options that downtown areas provide.

As you browse the downtown area, don’t forget to immerse yourself in the local entertainment scene. Many downtown areas boast theaters, concert venues, and live music performances, offering a blend of cultural and entertainment experiences. Catch a movie, attend a live theater show, or simply enjoy the lively street performances that often take place in downtown areas.

Lastly, don’t overlook the importance of simply taking in the sights and sounds of the downtown area. From busy city streets to serene parks, downtown areas offer a variety of environments to relax and enjoy the bustling atmosphere. Whether you prefer people-watching, taking a leisurely stroll, or sitting in a quaint café, the downtown area is the perfect place to soak in the ambiance of the city.

In conclusion, browsing the downtown area is a fantastic way to explore and experience the heart of a city. With its mix of shopping, cultural attractions, dining options, entertainment, and overall vibrant atmosphere, the downtown area offers something for everyone. So next time you find yourself in a new city or even in your own hometown, take the time to browse the downtown area and discover all that it has to offer.


In conclusion, Winchester, VA, offers a wide range of activities to unlock and enjoy. From exploring the interactive exhibits at the Shenandoah Valley Discovery Museum and discovering the rich history at Stonewall Jackson’s Headquarters Museum and Cedar Creek and Belle Grove National Historical Park to taking a scenic drive on the Skyline Drive and browsing the charming downtown area, Winchester has something for everyone.

Whether you’re interested in outdoor activities, art and history, or local wineries, Winchester has it all. And with its vibrant arts scene, delicious eateries, and friendly community, it’s no wonder that Winchester is a popular destination for visitors and locals alike.

So if you’re looking for a fun and exciting getaway, make sure to add Winchester, VA to your list of must-visit destinations. With so many incredible activities and attractions to explore, you’re sure to have a memorable and enjoyable experience.


Q: What are some of the best activities to do in Winchester, VA?

A: Some of the best activities in Winchester, VA include visiting museums like the Shenandoah Valley Discovery Museum and the Museum of the Shenandoah Valley, exploring historic sites like Stonewall Jackson’s Headquarters Museum and Cedar Creek and Belle Grove National Historical Park, enjoying outdoor activities at Jim Barnett Park, taking a scenic drive along the Skyline Drive, discovering local wineries, and browsing the downtown area.

Q: What is the Shenandoah Valley Discovery Museum?

A: The Shenandoah Valley Discovery Museum is an interactive museum located in downtown Winchester that offers hands-on learning experiences focused on science, technology, engineering, and math (STEM).

Q: What can I expect to see at the Museum of the Shenandoah Valley?

A: The Museum of the Shenandoah Valley houses a vast collection of artifacts, art, and decorative objects related to the history and culture of the Shenandoah Valley region. Visitors can explore the galleries, stroll through the beautiful gardens, and learn about the heritage and traditions of the area.

Q: What is the significance of Stonewall Jackson’s Headquarters Museum?

A: Stonewall Jackson’s Headquarters Museum is housed in the former headquarters of General Thomas J. “Stonewall” Jackson and offers insights into the life and military strategies of this prominent Confederate general. Visitors can tour the headquarters, see exhibits related to the Civil War era, and learn about Winchester’s role during this time.

Q: What activities are available at Jim Barnett Park?

A: At Jim Barnett Park, you can enjoy a variety of outdoor activities, including walking trails, picnic areas, sports fields, a disc golf course, an outdoor pool, tennis courts, and a playground. It’s a great destination for families and individuals who love being active.

Q: What is the Skyline Drive?

A: The Skyline Drive is a scenic road that stretches for 105 miles through the Shenandoah National Park, offering breathtaking views of the Shenandoah Valley and the Blue Ridge Mountains. Along the drive, you’ll find numerous overlooks and hiking trails to enjoy the beauty of nature.

Q: What can I see at Cedar Creek and Belle Grove National Historical Park?

A: Cedar Creek and Belle Grove National Historical Park commemorates the site of the American Civil War Battle of Cedar Creek. Visitors can explore the battlefield, visit the Belle Grove Plantation, and learn about the events that occurred during this historic battle.

Q: Are there any wineries in Winchester, VA?

A: Yes, Winchester is located in the heart of Virginia’s wine country, and there are several wineries in and around the city. These wineries offer tastings, tours, and events throughout the year, showcasing the best of Virginia’s wine production.

Q: What can I do in Winchester’s downtown area?

A: Winchester’s downtown area is full of charm and character. You can take a stroll down the pedestrian-friendly Loudoun Street Mall, shop for antiques and unique gifts, sample delicious cuisine at local restaurants, and enjoy the vibrant arts scene with art galleries and live performances happening regularly.