Winchester, Virginia, is a charming little city situated in the hills of the Shenandoah Valley. It has a very rich history, which you can learn at one of the museums in the city. It is also home to a lot of historic structures and landmarks. Nature-lovers would also appreciate the city with its hills and countryside that surrounds it, so you can hike, swim in lakes, harvest at farms and orchards, and indulge in many other activities. Get to learn more about the best things to do in Winchester, Virginia, and bring your family and friends to visit the city on your next vacation.
1. Break some sweat at Jefferson Street Trail Head
Editor's Note: There's no photo available at the time of writing
Jefferson Street Trail Head serves as one of the entry points of The Trails at the Museum of the Shenandoah Valley, which covers 90 acres (36.42 hectares) of land area. If you’re dropping by with your car, you can use the free parking space on the trailhead.
If you want a refreshing ambiance, this trailhead is a perfect spot for walking and cycling. If you want, you can also bring your furry friend for a quick run. As you stroll past the other trails, you’ll also come across splendid installation artworks.
Jefferson Street Trail Head
Address: Jefferson St, Winchester, VA 22601, United States
Opening hours: Open 24 hours daily
Price: Free entry
2. Taste craft beers at Broken Window Brewing Company
Editor's Note: Photo taken from the establishment's official social account
Posted by Broken Window Brewing Co. on Friday, September 9, 2022
Broken Window Brewing Company is a must-visit for lovers of craft beers. You can relax here and try its oatmeal stout with 4.5% alcohol by volume level. If you want more fun, you can also order its winter warmer with 9.1% alcohol by volume level.
This brewery offers board games for entertainment alongside its indoor and outdoor seating options. If you’re looking for a great place to hang out with your colleagues or loved ones, this point of interest might be the right fit for you.
Broken Window Brewing Company
Address: 14 W Boscawen St, Winchester, VA 22601, United States
Website: Broken Window Brewing Company
Opening hours: Mon - Thu: 4pm - 10pm; Fri: 4pm - 11pm; Sat: 1pm - 11pm; Sun: 2pm - 8pm
3. Catch majestic live performances at Bright Box Theater
Situated at the heart of the city, Bright Box Theater serves as one of the primary event venues in the area. Since 2013, it hosts live music and comedy performances throughout the year. Aside from this, locals have also booked this place to stage big celebrations such as private parties, weddings, reunions, and the like.
To give back to the community, it regularly collaborates with other institutions for fundraisers and charity events. Ticket prices vary per show, so make sure to stay tuned for the upcoming performances of this spectacular theater.
Bright Box Theater
Address: 15 N Loudoun St, Winchester, VA 22601, United States
Website: Bright Box Theater
Opening hours: Wed - Fri: 10am - 4pm (closed on Sat - Tue)
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4. Reconnect with nature at Abrams Creek Wetlands Preserve
Editor's Note: Photo taken from the establishment's official social account
With an area of 25 acres (10.12 hectares), Abrams Creek Wetlands Preserve serves as a sanctuary for numerous birds and plant species. In fact, 20 out of over 300 plant species in this preserve belong to the state’s list of rare plants. This natural landmark is also home to marshes and swamps covered by trees and shrubs.
You can walk along the area or ride your bike while appreciating the serene view of nature it offers. As you traverse the route, take some pauses and check the informative posters at different stops across the wetlands.
Abrams Creek Wetlands Preserve
Address: W Jubal Early Dr, Winchester, VA 22601, United States
Website: Abrams Creek Wetlands Preserve
Opening hours: Open 24 hours daily
Price: Free entry
5. Shop and explore Old Town Winchester
You will never run out of things to see as you wander through the Old Town Winchester. Also known as the Loudoun Street Pedestrian Mall, this brick-lined street is famous for its restaurants, shops, a Civil War Museum, and other historic buildings. There’s also a splash pad for kids to have fun during summer. It also becomes a venue for different events such as a summer Farmer’s Market, and Apple Blossom Festival.
Old Town Winchester
Address: Loudoun St. Winchester, VA, United States
Website: Old Town Winchester
6. Know the history at Museum of the Shenandoah Valley
Museum of the Shenandoah Valley preserves and exhibits the history, art, and culture of the Shenandoah Valley area. The museum complex’s main feature is the museum building, designed by the famous architect Michael Graves. There’s also a vast garden and a historic home that was built during the 18th century. The museum itself features several galleries and exhibits that display a lot of artifacts, art pieces, documents, old maps, and a lot more that was gathered in the Shenandoah Valley region.
Museum of the Shenandoah Valley
Address: 901 Amherst St, Winchester, VA 22601, United States
Website: Museum of the Shenandoah Valley
Opening hours: Tue - Sun: 10am - 5pm (closed on Mon)
7. Go back in time at Stonewall Jackson's Headquarters
Known before as the headquarters of General Thomas “Stonewall” Jackson during the 1800s, this Gothic home located along the Hudson River is now a museum that honors the bravery and the military expertise of the late general. In fact, his office was still perfectly preserved and still looks just the same when he was still using it back in his days. It is also home to the largest collection of Stonewall Jackson memorabilia that still exists and also features personal items owned by his different staff members. One of the most important items in the museum includes his personal prayer table and a large collection of family artifacts.
Stonewall Jackson's Headquarters
Address: 415 N Braddock St, Winchester, VA 22601, United States
Opening hours: Mon - Sat: 10am - 4pm; Sun: 12pm - 4pm
8. Relax at Jim Barnett Park
Editor's Note: There's no photo available at the time of writing
If you are in dire need of some fresh air, exercise, or want to indulge in fishing, then Jim Barnett Park would be the best place for you to go. It is home to over 270 acres (109.27 hectares) of parkland, with over 170 acres (68.80 hectares) of lush green space and amenities which include several playgrounds, pavilions, picnic areas with barbecue grills, indoor and outdoor pools, outdoor basketball courts, tennis courts, recreation center, walking and fitness trails, disc golf course, dog park, arboretum, fishing lake, horseshoe courts, and a BMX track.
Jim Barnett Park
Address: 1001 E Cork St, Winchester, VA 22601, United States
Opening hours: Mon - Fri: 5:30am - 9:30pm; Sat: 9am - 6pm; Sun: 12pm - 6pm
9. Taste some wine at James Charles Winery and Vineyard
Founded in 2015, James Charles Winery and Vineyard tells the story of the Bogaty family through their old-style and world-class wines right at the heart of Shenandoah Valley in Virginia. You will surely feel like you are at the vast wineries and vineyards of France when you come to visit. Come and enjoy their quality wines that feature bold, full-bodied, and complex flavors.
James Charles Winery and Vineyard
Address: 4063 Middle Rd, Winchester, VA 22602, United States
Website: James Charles Winery and Vineyard
Opening hours: Mon - Thu: 12pm - 6pm; Fri: 12pm - 9pm; Sat: 12pm - 8pm; Sun: 12pm - 5pm
10. Visit Patsy Cline Historic House
Patsy Cline Historic House was the former home of Virginia Patterson Hensley. Here she lived from 1948 to 1953 before she became a famous country music star and gained popularity as Patsy Cline. This Greek revival home has become a museum that was dedicated to her life and music career. The home has been a witness to her hard work and dedication to become a musician. Currently, it is only open seasonally for tours, which includes a tour of her garden. There’s also a gift shop where visitors can buy items and memorabilia related to Patsy Cline.
Patsy Cline Historic House
Address: 608 S Kent St, Winchester, VA 22601, United States
11. Walk or ride a bike at Third Winchester Battlefield Park
Editor's Note: There's no photo available at the time of writing
Featuring 5 miles (8.1 kilometers) of walking and biking trail, Third Winchester Battlefield is open for everyone all year round. One can embark on self-guided tours on this path that comes with signage and amazing views. The area also witnessed one of the biggest wars in the United States, where millions fought and around 8,600 casualties were recorded. After your walking or biking adventure, make sure to stop by their new visitor center and check out the Civil War-era displays and videos.
Third Winchester Battlefield Park
Address: 541 Redbud Rd, Winchester, VA 22603, United States
Opening hours: 5am - 9pm (daily)
12. Try the amazing food at George's Food and Spirit
Of course, your trip won’t be complete without trying out the local cuisine at Winchester. The best place for such an endeavor is George’s Food and Spirits. Located inside The George Washington Wyndham Grand Hotel along Old Town Winchester, tourists and locals love their casual yet elegant dining atmosphere. They serve the best and freshest dishes every day. Make sure to try their chicken pesto gnocchi, buttermilk fried chicken, and bacon horseradish sauce.
George's Food and Spirit
Address: 103 E Piccadilly St, Winchester, VA 22601, United States
Website: George’s Food and Spirit
Opening hours: 7am - 10pm (daily)
13. Enjoy small talks at Oak stone Craft Pizza and Bar
Bring your family and friends over for a great dining experience at Oak Stone Craft Pizza and Bar. It is an independent American restaurant that specializes in pizza. Here they cook in wood-fired ovens made of homemade dough and topped with the best ingredients. They also serve side dishes and salads, which are perfect to be paired with their fine collection of beers and wines.
Oak stone Craft Pizza and Bar
Address: 1000 Valley Ave, Winchester, VA 22601, United States
Website: Oak stone Craft Pizza and Bar
Opening hours: Tue - Thu: 11:30am - 8pm; Fri - Sat: 11:30am - 9pm; Sun: 11:30am - 7:30pm (closed on Mon)
14. Stay at Hilton Garden Inn Winchester (from USD 109)
Located just a few minutes away from the Old Court House Civil War Museum and George Washington’s Headquarters, Hilton Garden In Winchester is the perfect place for you to stay. Each room comes with free Wi-Fi access, a flat-screen TV, a microwave, a mini-refrigerator, an iPod docking station, an in-room safe, a living area, and a sofa bed. Guests can also enjoy their indoor pool, fitness room, convenience store, and laundry facilities.
Hilton Garden Inn Winchester
Address: 120 Wingate Drive
1.51 km (1.0 mi) from Jim Barnett Park
Explore Winchester, Virginia
Winchester in Virginia indeed offers a great mix of history and nature for tourists and locals alike. Make your experience in the city even more enjoyable by trying out the best things to do in Winchester, Virginia.
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