Location: Winchester
Top Things to do in Winchester
Top 10 Things to do Good for Couples in Winchester, Virginia (VA)
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. Winchester Little Theatre
Overall Ratings
5.0 based on 26 reviews
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.
2. Rocking S Ranch
Overall Ratings
5.0 based on 386 reviews
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.
3. Briede Family Vineyards
Overall Ratings
5.0 based on 9 reviews
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.
4. Museum of the Shenandoah Valley
Overall Ratings
4.5 based on 521 reviews
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.
5. Bright Box Theater
Overall Ratings
4.5 based on 36 reviews
Reviewed By MikeGuev - Winchester, United States
In sleepy little Winchester is a cool venue called the Bright Box... from comedy shows to amazing concerts this place has it all. Unique events and artists play here all the time and you need to check their schedule frequently to see if they are booking some a listers! Many of the comedians oh have seen on TV or heard them on XM..! Food is good and getting better all the time as they consistently tweak the menu.
6. Marker-Miller Orchards
Overall Ratings
4.5 based on 76 reviews
A Century Farm offering a variety of fresh fruits and vegetables available in our market and for pick-your-own. (Please check our website for availability for seasonal pick-your-own). We have a large selection of jams/jellies, fruit wines, honey, and no sugar added items to choose from. Visit our on-site bakery for pies, cakes, cookies, and apple cider donuts and our sweet shop for fresh made fudge and hand dipped ice cream.
Reviewed By CharleneW560
We had a great day picking a bag of apples- Crispin variety. I like to make pies and applesauce so I bought 2 boxes of 2nds.
7. Escutcheon Brewing Co
Overall Ratings
4.5 based on 29 reviews
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.
Reviewed By 601georged - Winchester, United States
We had looked for breweries close to us and found Escutcheon after tasting the Christmas Ale in Union Jack Pub and Restaurant. The tasting room features about half light beers and half heavy beers, is very clean and has a friendly server. The beer not to miss is the Winter Ale (AKA Christmas Ale). Full of flavor, medium in body with several different spice flavors brings out the season. A mixture of ales, stouts and IPAs makes this a must visit. Food can be brought in or ordered in to eat. So if you are looking for a local brewery with great tasting beers, check this out.
8. Old Town Winchester Walking Mall
Overall Ratings
4.5 based on 16 reviews
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.
Reviewed By JeffreyE414
We enjoy walking the brick mall and eating at one of the many cafes. It's a very nice area to stroll with children and take in the interesting shops as you munch on a cone of ice cream. I recommend a planning a romantic dinner. The surrounding streets also have restaurants.
9. Carmike Cinemas
10. Alamo Drafthouse Cinema
Overall Ratings
4.0 based on 91 reviews
Reviewed By 244amberg - Inwood, United States
I took my daughter and my friend's daughter here on a Sunday. It was the free screening of "The Wizard of Oz" and we had a great time. I think the 4th row is probably the best row to see a movie from. I'd been here before but this was my best viewing experience. Since our tickets were free, we splurged a little on food and drinks. I believe this is the only theater in the area with waitstaff so it was a fun experience. Our waiter was fast and attentive. It is worth mentioning that we went during the pandemic so face masks were required if you were not eating or drinking. They also leave buffer seating between your party and the next. The menu is limited (still plenty to choose from).
