What to do and see in Winchester, Virginia (VA): The Best Things to do

February 10, 2022 Lean Nau

Sitting at the northernmost corner of Virginia in the Shenandoah Valley, Winchester offers visitors the chance to explore historical sites, museums, vineyards, farmers' markets, and tree-lined Old Town streets once wandered by the likes of George Washington and Stonewall Jackson. The fruitful fields of the surrounding Frederick County have earned the area the title "apple capital of the world," with the city hosting the Shenandoah Apple Blossom Festival annually for almost a century.
Restaurants in Winchester

1. Rocking S Ranch

564 Glaize Orchard Rd, Winchester, VA 22603-2408 +1 540-678-8501 http://www.therockingsranch.com
Excellent
98%
Good
2%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 386 reviews

Rocking S Ranch

Reviewed By anna7753TK

Had an amazing ride with Mr. Bill, he is extremely friendly and a great guide. The trail was beautiful and the horses were very calm and enjoyable to ride. Highly recommend for anyone looking for a fun getaway, day activity, etc.

2. Stonewall Jackson's Headquarters

415 N Braddock St, Winchester, VA 22601-3921 +1 540-667-5505 http://winchesterhistory.org/stonewall-jacksons-headquarters/
Excellent
76%
Good
20%
Satisfactory
3%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 259 reviews

Stonewall Jackson's Headquarters

Season: Open Daily April 1 to October 31 BE SURE LISTING SHOWS WE ARE CLOSED FOR THE OFF SEASON. Wartime home of Stonewall Jackson in wintertime of 1861-62. Contains numerous Jacksonian items, including furniture, prayer table and desk. His well worn daily prayer book , a gift from his sister, is also on display.

Reviewed By lisawL4142TW

We had a great tour with a very knowledgeable guide who was able to answer all our questions. This house museum had so many authentic period pieces and personal objects from Jackson and his contemporaries.

3. Museum of the Shenandoah Valley

901 Amherst St, Winchester, VA 22601-3305 +1 888-556-5799 [email protected] http://www.themsv.org
Excellent
67%
Good
26%
Satisfactory
5%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 521 reviews

Museum of the Shenandoah Valley

The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house dating to the eighteenth century, six acres of spectacular gardens, and a 50,000-square-foot museum featuring changing exhibitions, a permanent display of miniature houses, and an expansive gallery exploring the history and decorative arts of the Shenandoah Valley. The galleries are open year-round; the house and gardens April through October. The property was passed through generations of Wood and Glass families until being acquired by Wood descendant and MSV benefactor Julian Wood Glass Jr. (1910–1992) between 1952 and 1955. Glass and his partner at the time, R. Lee Taylor (1924–2000), worked together to transform the site and its Glen Burnie House—built in 1794 by James Wood’s son Robert—into a country retreat where the couple entertained in high style.

Reviewed By aroundtheworld_FC - Winchester, United States

I love going to the MSV! I've been a member for a while now and always discover something new with each and every visit. The gardens are amazing in the late summer-early fall and the main museum has wonderful rotating exhibits (I got to see a few Warhol's and a Lichtenstein just the other day) as well as a nice permanent collection.

4. Shenandoah Valley Civil War Museum

20 N Loudoun St, Winchester, VA 22601-4716 +1 540-542-1145 http://www.civilwarmuseum.org/
Excellent
49%
Good
40%
Satisfactory
7%
Poor
3%
Terrible
1%
Overall Ratings

4.5 based on 190 reviews

Shenandoah Valley Civil War Museum

Reviewed By Je_suis_perdu1973 - Richmond, United States

One of the best military museums I've ever visited. I especially enjoyed the Civil War-era graffiti. Very interesting! I don't think there are many Confederate museums with that many historical objects that are still open to the public. The old court room was really cool. My kids loved visiting here.

5. Shenandoah Valley Discovery Museum

19 W Cork St Pre-purchased Tickets Required, Winchester, VA 22601-4741 +1 540-722-2020 [email protected] http://www.discoverymuseum.net
Excellent
66%
Good
26%
Satisfactory
7%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 177 reviews

Shenandoah Valley Discovery Museum

Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts.All exhibits, activities and experiences provided by the Discovery Museum adhere to the following philosophical guidelines:Exhibits, activities and programs are interactive, participatory and informal, and give visitors opportunities to experiment, have fun playing, use their imaginations and share ideas.Visitors are engaged at their own level of expertise and experience.Activities and programs are multi-sensory, authentic, honest, and factual.The Museum works in a spirit of cooperation and partnership with educational, cultural, governmental and community organizations.

Reviewed By 519kathied - Edinburg, United States

All ages kids will love this hands on museum. There are 3 stories of activities and displays. There is a rescue unit to explore, an apple processing set, etc. There are specific activities that have to be signed up for. Always something to entertain and excite the kids.

6. Patsy Cline Historic House

608 S Kent St, Winchester, VA 22601-4664 +1 540-662-5555 [email protected] http://www.celebratingpatsycline.org
Excellent
68%
Good
22%
Satisfactory
8%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 158 reviews

Patsy Cline Historic House

COVID-19 INFORMATION: With the safety of our staff, volunteers and guests in mind we will remain temporarily closed until further notice due to COVID. Guided tours of the Patsy Cline Historic House are conducted in a very close and intimate setting. The house can not open and adhere to the Governor's Forward Virginia current opening mandates including social distancing in such a small museum space. ABOUT THE HOUSE: The house stands as an icon for Patsy Cline fans and admirers hoping to know first hand the story of Patsy’s early years. Patsy Cline’s home offers a window on the famed singer’s early road to stardom.

Reviewed By underdog63

It was a joy to spend time at the Patsy Cline House seeing the memorabilia and hearing the story of Patsy. The volunteers here are a great value and love to share the story and visit with guests. Stop by and enjoy a peaceful visit with wonderful people.

7. Kernstown Battlefield and Pritchard House

610 Battle Park Drive, Winchester, VA 22602 +1 202-302-9129 http://www.kernstownbattle.org/
Excellent
67%
Good
25%
Satisfactory
8%
Poor
0%
Terrible
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Overall Ratings

4.5 based on 61 reviews

Kernstown Battlefield and Pritchard House

Reviewed By janhP5062CT

Expected to drive or walk around the battlefield, reading markers. Instead, we got a personal tour in a golf cart by one of the volunteers (thanks, Bill!), with a running narrative of the battles and more. Then a tour of the Pritchard House given by another volunteer, ending with the recreation of the field hospital that was created in the lower level of the house during the battles, again with a knowledgeable talk by a volunteer. Get the gist? Volunteers not only raised the money to save this battlefield from development, they now maintain it and are restoring buildings and landscapes as they can. Highly recommended.

8. Handley Regional Library

Picadilly St, Winchester, VA +1 540-662-9041 http://www.oldtownwinchesterva.com/business-directory/attractions-museums/handley-regional-library/
Excellent
76%
Good
20%
Satisfactory
4%
Poor
0%
Terrible
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Overall Ratings

4.5 based on 150 reviews

Handley Regional Library

Reviewed By NJLivingston

This building is stunning and we had no plans to visit but once we spotted it, we had to go inside. It is a beautiful building with a lovely duomo. Great to explore and has lots of fantastic reading niches. Huge section for kids and teens on second floor. Spiral stairwells were fun.

9. Jim Barnett Park

1001 E Cork St, Winchester, VA 22601-5575 +1 540-662-4946 http://www.winchesterva.gov/parks
Excellent
50%
Good
36%
Satisfactory
14%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 28 reviews

Jim Barnett Park

Reviewed By ShadowtheKitty - Painesville, United States

Disc Golf Course and Geocaching. Very nice disc golf course with some unique features. Didn't lose any disc while playing disc golf. Were several other groups also playing, but we weren't crowded. Geocaching in this park is great for beginners and for younger geocaches. Very unique. One of the geocaches I wouldn't do if it is where I think it is, for safety reasons don't go into storm sewers due to potential for oxygen deficient atmosphere. But the others were good.

10. I Love Kickboxing

3051 Valley Ave #106, Winchester, VA 22601-2658 +1 540-300-7739 http://www.ilovekickboxing.com
Excellent
99%
Good
0%
Satisfactory
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Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 71 reviews

Reviewed By chuffman2219

I am currently doing the 6 week challenge here and I love it! I love the instructors, the gym itself, and the classes are high intensity and I feel like I am pushed beyond what I think I can do in each class and I feel so much better than when I started! Do yourself a favor and join a class!

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