A Winchester Virginia getaway or day trip offers tasty dining and craft beer, beautiful scenery, interesting history, and unique fun for every age group. The walkable downtown features a pedestrian mall lined with restaurants, shops, historic architecture, museums, and even a brewery or two. Within a few blocks are more fun and funky places to explore.
The Winchester Virginia getaway fun extends beyond the downtown. Nearby farms, small country roads, and trails are perfect for scenic exploring. Winchester is less than two hours from Washington DC, so it’s ideal for a last-minute day trip. But we highly recommend a longer visit to enjoy everything the area has to offer.
Start at the Winchester Frederick County Visitors Center to pick up information and learn a little about the area. You’ll find self-guided walking tour maps, along with information about guided tours and other special events. Next, head to Old Town Winchester and start exploring.
Explore more: 15 Fun Northern Virginia Small Towns to Visit Now.
Some of our visits to Winchester were hosted by the Winchester Frederick County Convention and Visitor Bureau. All opinions, text, and photos are our own.
Downtown Places to Visit on a Winchester Virginia Getaway
Old Town Pedestrian Mall
You could spend several hours wandering through Winchester’s Loudoun Street Pedestrian Mall. The brick-clad street boasts restaurants and shops, plus a Civil War museum, and other historic buildings. At the southern end, kids can play in a splash pad during the warmer months. The mall hosts special events throughout the year, including a summer Farmer’s Market, and seasonal fun like the popular, spring Apple Blossom Festival.
Shenandoah Valley Discovery Museum
Kids and families can play as they learn on four levels of interactive exhibits at the Shenandoah Valley Discovery Museum. There are plenty of hands-on activities at the museum for kids and parents to try together. Don’t miss the pretty views from the rooftop level! The Discovery Museum is one of the best places to visit in Winchester with kids.
Handley Library and Downtown Architecture
A block from the pedestrian mall is one of the finest Beaux-Arts buildings in the area, the Handley Regional Library. The beautiful exterior was designed to suggest an open book. The rotunda forms the spine and two wings are the book’s covers. Climb the pretty curving stairwell inside for a closer look at the stained-glass rotunda.
Mount Hebron Cemetery
Gravestones in the Mount Hebron Cemetery date to the 1760s. Four separate burying grounds share a common entryway and enclosure. In one section, the remains of a Lutheran Church are surrounded by graves from the late 18th century. The nearby labyrinth offers a place for quiet reflection. The Stonewall Confederate Cemetery was dedicated shortly after the Civil War in 1866. It is the resting place of 2,576 Confederate soldiers who died in the area.
More Historic Sites in Downtown Winchester
George Washington developed his reputation and skill as a commander while living and working in the Winchester area. Visit George Washington’s Office Museum to learn about his time in the area, Here he planned and oversaw the construction of Fort Loudoun.
Winchester changed hands 72 times during the Civil War, more than any other U.S. town. Today, that history is preserved and interpreted at several area sites. The Shenandoah Valley Civil War Museum is located on the pedestrian mall. It occupies a courthouse that was used as a hospital and prison during the Civil War. Nearby, Stonewall Jackson’s Headquarters is preserved as a museum.
Nearby Things to Do on a Winchester Virginia Getaway
Museum of the Shenandoah Valley
Explore the art and gardens at the Museum of the Shenandoah Valley to learn more about the people and places of the region. The collection includes an incredible display of miniature houses and furniture. Outdoor lovers should stroll through the Glen Burnie Gardens. The Asian-influenced water garden is particularly beautiful.
State Arboretum of Virginia, Blandy Experimental Farm
The University of Virginia conducts research and trains budding scientists at the State Arboretum of Virginia, Blandy Experimental Farm. The farm also preserves a diverse collection of trees and plants. Several trails and a loop drive make it easy to explore the collection and enjoy the beauty.
Shop at a Local Farm Near in Frederick County Virginia
Local farms are fun stops for tasty fruit, produce, and other treats. They also invite a scenic drive on country roads. Richard’s Fruit Market is a fifth-generation farm (there were three-generations on site when we stopped by). They sell their own produce, meats, and of course, fruit at the farm stand. They also have a pick-your-own flower garden, animals to visit, and a very cool apple grader that buffs and sorts the apples.
Another popular farm stop is Marker-Miller Orchards and Farm Market. The on-site bakery makes yummy apple cider donuts, and there’s a large playground out back for the kids. Look for the big apple near the parking lot for a fun photo spot. The Homestead Farm at Fruit Hill Orchard is a smaller farm with a lovely organic garden and a shop selling gifts and treats.
Take a Hike to a Beautiful View
The hike to Eagle Rock Overlook is a short climb that’s a bit of a workout. It’s not too difficult for younger kids as long as you take your time. The pay-off is a series of overlooks and impressive eastward views of the Shenandoah Valley countryside. One overlook even has a stone bench that makes a good picnic spot on this 3-mile out-and-back hike.
The trail begins at a small parking area on the Virginia, West Virginia border. Follow the blue-blazed Tuscarora Trail to the overlook.
The trailhead for the hike is a little hard to find via GPS, so here is a map to the turn onto Capon Springs Grade/route 609. Follow the dirt road uphill until you see a small parking area on your left, just before the West Virginia line. The trail begins across the street, marked with a Great Eastern Trail sign.
>> Find more great hiking in our Guide to Shenandoah National Park Central District.
Learn and Shop with the Artisans in Berryville VA
Many artisans make their home and sell their wares in the small town of Berryville, in neighboring Clark County. Begin at the Barns of Rose Hill Cultural Arts Center to see current exhibits and learn about the artisans in town. The Barns also host special events and live entertainment. Next, wander through the downtown area, visiting shops and speaking with artisans about their creations.
Tour the Mansion at Belle Grove Plantation
Belle Grove Plantation is an antebellum farm once owned by Isaac and Nelly Hite. Nelly was the sister of future president James Madison. Tours share details of life on the plantation during the early 1800s and the period furnishings of the manor house. Outside, visitors can stroll the gardens and grounds in the pastoral country setting in Middletown.
Where to Eat in Winchester Virginia
The range of dining options in Winchester VA is extensive and diverse. Plan your visit with our round-up of fantastic local restaurants in and near Old Town Winchester. We’ve highlighted a few of our favorites below.
The pedestrian mall is a good bet for lunch, with a wide range of restaurant styles and price ranges. The Union Jack Pub makes tasty fish and chips. Oak Stone Pizza is our pick for delicious pies baked in a brick oven.
Violino, on the pedestrian mall, is a cozy spot for a romantic dinner of fresh, Northern Italian dishes. Or head to the Village Square Restaurant for contemporary American dishes in a historic building on the mall. During Restaurant Week, our three-course meal included delicious ravioli and a generous banana sundae.
Drink Local Craft Beer and Cider
There are several excellent breweries in downtown Winchester. Alesatian Brewing Company operates a second-floor taproom on the pedestrian mall, with a range of beers from the classic to the funky. A block away, you’ll find Winchester Brew Works, a majority woman-owned-and-brewed nan-brewery with delicious beer and a happy vibe. Their ESB is fantastic! A bit further north, Escutcheon Brewing Company brews and pours a range of beers including some tasty stouts.
Cider lovers should keep an eye out for Winchester Ciderworks, a cidery producing delicious drinks from all those local apples. The flagship Malice is crisp and refreshing, and they also produce fruit-based and barrel-aged ciders.
>> Explore more great craft breweries with our guide to 12 Virginia Beer Trails.
Where to Stay on a Winchester Virginia Getaway
There are several excellent places to stay in Winchester, both in and outside the downtown area. Book a stay at one of our top picks listed below, or check rates and availability at all Winchester Virginia hotels.
Best Place to Stay in Downtown Winchester
The George Washington Hotel combines elegance, comfort, and a perfect location for exploring downtown Winchester. The Wyndham Grand Hotel occupies a Georgian Revival brick building just a block from the pedestrian mall. Your room is close to everything, but away from nighttime noise.
Free wifi, comfy beds, and a welcoming on-site bar and restaurant make the GW a great base for your Winchester Virginia getaway. Relax with a massage or facial at Saumaj, the on-site spa, or soak in the beautiful indoor, saltwater pool, modeled after a Roman bathhouse.
Unique Places to Stay near Winchester
Book a romantic getaway at the Inn at Vaucluse Spring for a beautiful dose of elegance and history in the countryside. The inn is located in the small town of Stephen’s City, just south of Winchester. There are six different guest houses to choose from.
We highly recommend the historic Mill House, with fireplace, small kitchen, bedroom with expansive windows, and jacuzzi tub. Best of all, the mill has a private patio overlooking a small pond fed by Vaucluse Spring. Breakfast in the manor house is three courses of farm-to-table deliciousness and the whole experience is so relaxing.
Another option for a stay filled with country elegance is the Historic Rosemont Manor in Berryville. Rosemont is a popular venue for weddings and corporate retreats, but they rent individual rooms when no events are being held. The sumptuous rooms are unique and lovely, and the grounds are spectacular. Rosemont Manor also offers traditional English teas throughout the year.
There are also many vacation rentals in Winchester VA perfect for travelers who want a home setting with specific amenities.
Whether you visit for a day or a longer stay, you’ll find plenty of fun and interesting things to do and see in Winchester Virginia and the surrounding towns. It’s a short drive from the busy Washington DC area, but the country vibe feels much further away.
Map of Things to Do in Winchester Virginia
Click our handy map to plan your visit to Winchester Virginia and Frederick County.
- Northern Shenandoah Valley Road Trip: Winchester to Harrisonburg
- Southern Shenandoah Valley Road Trip: Staunton to Lexington
- 8 Great Things to do in Roanoke Virginia
- Outdoor Adventures in Virginia’s Blue Ridge
Published 2017, last updated 2021.