Things to do & places to visit in Winchester, Virginia, United States

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.

Winchester city in Virginia, United States. Timezone: America/New_York, current date and time: Wednesday, May 08, 2024, 23:45.

Top things to do (25)

Top places to visit (30 attractions) view more »

5.0 Rocking S Ranch (471 reviews)
- What a great ride!
Wednesday: 10:00 AM - 6:00 PM Ranches

Bill (the owner/operator) was fantastic! Our 90 min trail ride was more like two hours. It was just Bill, me, and my mom. The ride takes you through the woods, up and down some inclines, and through a creek (twice!) Horses were very gentle and well-behaved. Bill regaled us with stories/jokes and information about the area. We were staying at the Salamander Resort but booked our horseback riding at Rockin’ S because the price was way better and the ride was longer. Highly recommend! See more..
5.0 Stonewall Jackson's Headquarters (305 reviews)
- An incredible experience for the whole family
Speciality Museums • History Museums

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. See more..
5.0 I Love Kickboxing (71 reviews)
- Tough but so worth it!!
Wednesday: 6:00 AM - 12:15 PM, 5:00 PM - 7:30 AM Spent 1-2 hours Sports Camps & Clinics
Kickboxing is something I always wanted to try, and when I say they had a 6 Week Challenge it seemed like the right time to start something new. The staff at iLoveKickboxing - Winchester is awesome!! They are so sweet, told me I didn't even look my age. They push us beyond our limits to help us grow and be successful. They are kind and helpful to those of us who are a little inexperienced. After a week and a half of classes, I feel good and would highly recommend them! Thanks to Alyson and Haley, and all the staff. Y'all are rockstars!! See more..
5.0 Winchester Little Theatre (27 reviews)
- Great little theatre
Spent 2-3 hours Theaters

The Winchester Little Theatre was organized in 1929 "...to present, produce and encourage the production, acting and writing of plays..." by a group of persons interested in providing an outlet for their artistic interests and bringing to the community entertainment and culture. See more..
5.0 Briede Family Vineyards (11 reviews)
- This is a total gem. Love the ambience, scenery, and most especially the wine and the friendly, knowledgeable owners.
Wednesday: Spent 1-2 hours Wineries & Vineyards

We are small boutique winery located in the Shenandoah Valley. We are a different winery in that we grow "Hybrid" grapes. Our International award winning wines including our "Arandell" have won a Silver Medal recently in the 2020 International Sommelier Challenge in California in a blind tasting. Come sit and enjoy our charming venue with a glass of wine from one of the best winemakers in the state. Paul and I would love to share our passion for wine with you. Don't forget our selection of lovely sparkling wines and champagnes from around the world. See more..
5.0 Virginia Museum of Veiled History (7 reviews)
- A different kind of museum with a very important perspective.
Wednesday: Spent < 1 hour Speciality Museums • History Museums

See vivid evidence of the history behind the scenes -- the real history veiled by the powerful in Virginia. A Winchester resident wrote the Fugitive Slave Act. Another ran Virginia for 40 years but isn't spoken of. Another went from slavery to Congress. Proprietor and writer Larry Yates is there 11 am- 7pm Friday-Sunday with exhibits, videos and publications. See more..
4.5 Museum of the Shenandoah Valley (537 reviews)
- Well worth the stop!
Wednesday: 10:00 AM - 5:00 PM Spent 1-2 hours Art Museums • History Museums

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. See more..
4.5 Shenandoah Valley Civil War Museum (200 reviews)
- Very Enjoyable
Wednesday: 10:00 AM - 5:00 PM Speciality Museums

Located in the very middle of Old Town, this museum is in the former County Courthouse. All of the exhibits are on the second floor ( elevator is available ) and while on the small side offers a very extensive look at Winchester and it;s role in The Civil war. the main floor is the old courtroom and is also avilable to view. There is a small gift shop located where you purchase your tickets. Truly a worthwhile place to visit. See more..
4.5 Shenandoah Valley Discovery Museum (179 reviews)
- Visiting Grand babies
Wednesday: 9:30 AM - 11:30 AM, 1:30 PM - 3:30 PM Spent 2-3 hours Science Museums • Educational sites • Children's Museums

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. See more..
4.5 Patsy Cline Historic House (169 reviews)
- Wonderful short but interesting tour.
Wednesday: Spent < 1 hour Points of Interest & Landmarks

The Patsy Cline Historic House is now closed for the 2022 Season. We will reopen for the season in the Spring of 2023. ABOUT THE HOUSE: The house stands as an icon for Patsy Cline fans and admirers hoping to know firsthand the story of Patsy’s early years. Patsy Cline’s home offers a window into the famed singer’s early road to stardom. See more..
4.5 Handley Regional Library (152 reviews)
- Gorgeous Beaux-Arts style building
Wednesday: 10:00 AM - 8:00 PM Spent < 1 hour Points of Interest & Landmarks • Libraries

Incredible to see such a building among all the old colonial and Gothic revival style ones. We drove by, and our jaws dropped. Parked our car (most spaces are metered———- a quarter for 20 minutes), and after climbing some stairs, we were inside. You almost feel like you entered a sanctuary, there is something so special about the space. The library opened in 1913, and has been beautifully maintained. We walked through all the rooms, and admired the details, the art work, the massive fireplaces, the elegant spiral staircases, the dome stained glass ceiling, etc. We were so involved with the building, that we barely noticed the books. It’s nice that they have a small wall dedicated to the architects (from New York), who designed this jewel. See more..
4.5 Abram's Delight (77 reviews)
- Charming
Wednesday: 10:00 AM - 4:00 PM Historic Sites • Architectural Buildings

This is wonderful place to visit while in Winchester. It is the oldest home in the area built in 1754 I believe (or somewhere close to that.) It has many original victorian peices in it. Our guide was wonderul, explaining what each peice was and how it was used back then. There is also a period log cabin on the property which is also very neat. We really enjoyed this tour. See more..
4.5 Kernstown Battlefield and Pritchard House (65 reviews)
- The Field Hospital at Kernstown
Wednesday: Battlefields

We visited the Battlefield July 4th weekend, it was amazing! The view is so incredible from up on the hill, where we were driven in a golf cart, with a great description from the tour guide. Then we took a tour in the visitors center, but the best of all was a visit to the Field Hospital. There the docent did a complete, interesting and informative talk on the items in the cases, and all the artifacts that were in the room. She knew her subject matter thoroughly, and we learned so much about the hospital experience from the war. Highly recommended !! See more..
4.5 Stonewall Confederate Cemetery (60 reviews)
- Reverence of history
Cemeteries

If the hallowed grounds here do not touch you, you need to get right with God. We put flags on the graves every spring. Thank you to the brave men in gray. See more..
4.5 Winchester-Frederick County Convention & Visitors Center (44 reviews)
- Great place to stop for brochures and directions
Wednesday: 9:00 AM - 5:00 PM Spent < 1 hour Visitor Centers

Welcome to the Winchester area! We're the official Visitor Center and Tourism Office representing the City of Winchester and Frederick County, Virginia. Stop by any day of the week, 9am-5pm, to get personal and friendly information on the entire area. Enjoy our large and clean family-friendly bathrooms and gift shop offering local and regional items, souvenirs, official Virginia is for Lovers shirts and merchandise, and local beer, wine and cider. Free bus and RV parking available on-site. Need to stretch your legs? We're just steps from the Abram's Delight historic home, historical society museum, and Wilkins Lake which has a paved trail surrounding it. We're also on the edge of the Shenandoah University campus which has trails and paths throughout. A great stop if you have a dog that needs a walk as all areas mentioned above are dog friendly! See more..
4.5 Bright Box Theater (36 reviews)
- A Walking Mall Necessity!!
Wednesday: 9:00 AM - 11:45 PM Spent 2-3 hours Theaters

If you haven't been yet.. You don't know what you are missing. Great for hearing new music and meeting new people.. Even if your not into great music and new people.. Go to support the local beer. :) See more..
4.5 Escutcheon Brewing Co (29 reviews)
- Friendly staff, great beer
Wednesday: Spent 1-2 hours Breweries

Escutcheon Brewing is Winchester, VA's first and only micro brewery in operation. We strive to produce true-to-style classic beers - we don't do trendy and novel...we make solid styles, with an unwavering commitment to quality. Our flagship beers include a Kolsch, Vienna Lager, American Pale Ale, India Pale Ale, Dry Irish Stout and our newest beer, the John Riggins' 4th and 1 Pilsner...a classic pils brewed in collaboration with our friend and NFL hall-of-fame runningback, John Riggins. Come by our beautiful public taproom for a pint, a flight, a tour...whatever suits your fancy. See more..
4.5 Jim Barnett Park (28 reviews)
- Great beginner spot for geocaching or for younger geocachers
Wednesday: 5:30 AM - 9:30 PM Parks

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. See more..
4.5 Virginia Farm Market (20 reviews)
- Great in the fall
Wednesday: 8:00 AM - 6:30 PM Spent 1-2 hours Farmers Markets

apples, apples everywhere! pies, hand pies, apple cider donuts fresh out of the fryer, cider, and fresh picked! There also were pumpkin donuts, many different kinds of pies (half and whole), many different kinds of apples. Pumpkins too. Very busy on a late Sunday morning. Obviously a popular place. Parking right next to the building was busy, but they also use a field across the road where there was plenty of spaces. See more..
4.5 Winchester Ciderworks (14 reviews)
- Wonderful place to just relax
Wednesday: Spent 1-2 hours Wineries & Vineyards • Breweries

English-style dry hard ciders hand-crafted right here in Winchester, Virginia, from Shenandoah Valley apples. We invite you to our tasting room to try our varieties of hard ciders. From limited edition barrel aged ciders to our signature Malice, you'll never look at hard cider the same way again. See more..
4.5 Broken Window Brewing Co. (11 reviews)
- Great place for beer!
Breweries

I just returned from visiting Broken Window and believe this is an absolute jewel! Located in the pedestrian area of Old Town Winchester don’t miss this place. There is indoor and outdoor seating. Staff is super friendly and ready with suggestions for food to pair with their beer. There are board games to play and a trivia contest on Wednesdays so you better arrive early. If the Brown IPA is available, I highly recommend it. It offers a nice nutty Carmel flavor without the bitterness. Simply, Broken Window is a wonderful place to sit back and enjoy a beer. See more..
4.5 West Oaks Farm Market (8 reviews)
- Farm Market Meets Western Saloon
Spent < 1 hour Farmers Markets

This multigenerational family farm near Winchester has built a market, restaurant, and wedding venue on the premises. It's a bit out in the country. Most of the food sold in the market and restaurant is grown on farm or locally sourced. I had the "Ring of Fire" cheeseburger with jalapenos. The beef was very high quality. The atmosphere is comfortable for American deplorables. You'll be right at home here. See more..
4.5 Sacred Heart of Jesus Catholic Church (8 reviews)
- Sunday Evening Mass
Spent < 1 hour Churches & Cathedrals
A very reverential Mass. confessions are separately heard during the Service. Very friendly and welcoming greeters. See more..
4.0 Washington's Office Museum (124 reviews)
- Very Enjoyable
Wednesday: 10:00 AM - 4:00 PM Speciality Museums • History Museums

This is a very small museum and while there is only thing directly attached to Washington ( A lock of his hair ) the rest of the museum gives a very detailed insight into Washington as a very young man while living in Winchester. Our guide was very friendly and informative and the hour that we spent was well worth it. On Note Of Information. If you wish to save some money, you may purchase a combo ticket that will let you visit Stonewall Jackson's Headquarters as well. See more..
4.0 Third Winchester Battlefield (52 reviews)
- Excellent Battlefield Walking Tour
Battlefields

The 3rd Winchester Battlefield continues to develop nicely over the years. The 5 miles of trails are expanding into more meaningful loops and established trees are hiding views of I-81. This battlesite is a great place for a walk, jog, or other day out and memorializes one of the great battles of the Civil War. See more..
4.0 James Charles Winery & Vineyard (45 reviews)
- Ok wine, have to be a member for full experience
Wednesday: 12:00 PM - 6:00 PM Spent 1-2 hours Wineries & Vineyards

Founded in 2015, James Charles Winery is the embodiment of the Bogaty's family story. We make old-world style wines in the heart of Virginia's Shenandoah Valley AVA, which strongly resembles classic winemaking regions in France. Our wines are bold, full-bodied and complex. James Charles Winery & Vineyard is the northern Shenandoah Valley's premier winery, vineyard and wedding venue - located just outside of Winchester, Virginia, it's easily accessible from Interstate 81, US Route 11, Interstate 66, US Route 522, US Route 15, US Route 17, VA Route 7, Northern Virginia and Washington, DC, yet a world away in the rolling hills of the Valley's apple country. See more..
4.0 Old Town Winchester Walking Mall (26 reviews)
- Better Than Cars
Spent 2-3 hours Points of Interest & Landmarks • Historic Walking Areas • Scenic Walking Areas

Come enjoy a wonderful meal on the 2-block Walking Mall at one of 20 local restaurants, visit our unique shops, enjoy a cup of coffee at one of our 4 coffee shops or a craft beer at one of our 4 breweries. Two historic museums, a children's museum, and a public splash pad all accentuate your experience. Ample street, lot and garage parking is available. See more..
4.0 Winchester Brew Works (25 reviews)
- St Pattys Day
Breweries

Good selection of beer. They were all inticinf but my favorites we're the 2200 and the Happy Trails! See more..
4.0 Abrams Creek Wetlands Preserve (17 reviews)
- Nice walk along the wetlands
Spent 1-2 hours Nature & Wildlife Areas

Have visited this wetlands walk on every visit to Winchester. The surface is smooth pavement with one wooden bridge. Path runs thru wetlands, then beside old railroad track, and then behind some homes in nice neighborhood. Not very long but a nice place for a walk if you are in town and need to stretch your legs. Depending on when you walk, you can also grab a cup of coffee at The Daily Grind if you park in the shopping center on Jubal Early drive. See more..
3.5 Apple Blossom Mall (35 reviews)
- Can't keep stores, hit nova for "nice" places.
Wednesday: 10:00 AM - 9:00 PM Shopping Malls

As a local to this area I have had plenty of experience with this mall. High rental prices, not quite big enough walkways and stores, and a general lack of interest have made this mall a hodgepodge of stores with high turn-over. While not horrible, it is not a quality shopping destination. Also, avoid the attached carmine cinema at all costs. Go to the Alamo drafthouse for a fun movie watching experience, just be sure to get there early. See more..