30+ Fantastic & Fun Things To Do In Winchester VA

A weekend getaway or a day trip from nearby Washington, D.C, Baltimore, MD, Richmond, VA, or Harrisburg, PA to Winchester, VA, are all within a 90 minutes to less than 2½ hours of drive.

The northern Virginia city of Winchester has much to offer visitors.  Spend the day, weekend, or week exploring the pedestrian mall’s shops, George Washington’s Office, the Patsy Cline Museum, breweries, and historic architectural design.  You can even spend the day in nature exploring the Shenandoah Valley’s country road, trails, and farm markets.

Winchester Virginia

Explore the to-do list below and make Winchester more than a stop for gas as you switch from I-81 to I-66 or vise-versa.  You will be surprised at how much there is to do in this beautiful Shenandoah Valley town.

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How to get to Winchester

Winchester is an easy drive from almost anywhere since it is close to Interstates 81 and 66.  Unfortunately for those without transportation, it is a more challenging route since Amtrak and Greyhound do not have stops in Winchester.  The closest stops are in Harpers Ferry, MD and Front Royal, VA. 

The easiest way to get to Winchester is to jump in your car and head west on I-66 from Washington, D.C.  If you are coming from Harrisburg, it is a straight shot south for two hours on I-81. Baltimoreans need to travel west on I-70, then Route 340. The easiest way for Richmond folks to get to Winchester is to travel north on I-95 to Fredericksburg before heading north on Route 17, then finally west on I-66.

Old Clock in Winchester Virginia

Downtown Places to Visit

After arriving in Winchester, head to the Winchester Fredericks County Visitors Center.  Here you can learn how best to spend your precious time in town. Be sure to pick up a self-guided walking tour map, find out what special events are happening during your stay, and check out the list of available guided tours.

The Visitors Center offers a short video about Winchester that you can view to introduce yourself to the area. 

Those interested in more information about Winchester’s role in the Civil War should head to the Civil War Orientation Center for an excellent overview.

Patsy Cline fans will enjoy the exhibit Becoming Patsy Cline which showcases the early years of Patsy’s life.

The Visitors Center’s patio is a great location to enjoy a picnic as you look over Rouss Spring and the Jim Barnett Park.

Once you have collected all of your needed information and brochures, begin exploring Old Town Winchester.

Visit Old Town Winchester

The charming 250-year-old Old Town Winchester offers visitors lovely strolls past 60 shops to peruse, 30 delicious restaurants to dine in, a handful of fascinating museums to explore, and beautiful architecture to marvel over.

There will be something for everyone, with museums focusing on Stonewall Jackson, George Washington, Patsy Cline, and the children’s Shenandoah Valley Discovery Museum.

George Washington Office Museum in Winchester Virginia

Explore the George Washington Office Museum

When looking for things to do around Winchester, a stop at the George Washington Office Museum should be near the top of your list.

Visit the military office that George Washington used for 16 months from 1755 to 1756 as he planned and constructed Fort Loudoun. As you tour the museum, you will learn about his time in Winchester and see some personal artifacts of Washington’s, such as some of his surveying equipment and hair. Outside the museum, there is a Fort Loudoun cannon.

Handley Library in Winchester VA

Visit the Handley Library and Marvel at the Architecture

Just a block off the pedestrian mall, the Handley Regional Library sits.  Step back from the library and study the design of the center rotunda accompanied by the wings on each side. The library was built in a Beaux-Arts Classicism style and bear a resemblance to an opened book. Can you see the dome as the spine and the wings as the book cover and pages?

Mount Hebron Cemetery in Winchester VA

Mount Hebron Cemetery

The Mount Hebron Cemetery is a fascinating place to visit in Winchester.  The more than 30,000 graves dating back to the 1760s surround the Lutheran Church.

In the Stonewall Confederate Cemetery section, you will find the graves of over 2,500 Confederate soldiers who died in the Winchester area.

In another section, you will find graves from the late 18th century. Within the cemetery, you will find various influential and notable people like Confederate General Turner Ashby, library benefactor John Handley, and former VA governors Harry Byrd and Frederick Holliday.

The drive through the cemetery’s rolling fields is not only peaceful but picturesque.  If you want a quiet place to sit and reflect, the labyrinth is a perfect destination.

Old Town Pedestrian Mall

The two-block Old Town Pedestrian Mall on Loudoun Street has plenty of things to explore along the brick streets.

Not only can you enjoy the shops, restaurants, and museums, but the kids will need a change of clothes in the summertime after they enjoy the Splash Pad at the southern end of the mall.

If you happen to be in town on the first Friday of the month, take part in the First Fridays Celebrations of the Arts to meet local artists and watch live demonstrations. You will find fresh fruits and vegetables at the Farmer’s Market during the summer, and the Apple Blossom and Wine and Fine Art Festivals happen here each May.

If you want to search out the best deals, head to the mall on either Friday or Saturday.  However, if you are looking for a quiet place to walk, then visit on Sunday.

Patsy Cline's House in Winchester Virginia

Patsy Cline Historic House

Explore musical history at the Patsy Cline Historic House, half a mile from the mall. The country music legend, Patsy Cline, lived in the modest Winchester home from the age of 16 until she was 21.

Patsy Cline was one of the most influential singers of the 20th-century, and she is one who was able to successfully crossover from country music into pop music.

Shenandoah Valley Discovery Museum

The Shenandoah Valley Discovery Museum is one of the best attractions in Winchester for kids.  The museum has 19,000 square feet of fun interactive exhibits scattered across four floors that the whole family will enjoy.

When you need a breath of fresh air, head to the rooftop level and enjoy the fantastic views over Winchester.

Tour Stonewall Jackson Headquarters

The historic Hudson River Gothic Revival-style house along Braddock Street is a terrific place to visit in Winchester.  

As you tour Stonewall Jackson’s 1861 – 1862 Civil War headquarters, you will see Jackson’s prayer table and prayer book, along with family artifacts. You will also discover what his office would have looked like during his time there.

Apple picking in Maryland

Take Part in the Apple Blossom Festival

Attending the Apple Blossom Festival in Old Town is one of Winchester’s best things to do since nearly 250,000 people attend it each year.

The spring festival lasts for six days, so you can keep coming back and enjoying yourself. 

Check out all the local crafters and artisan booths, bring your lawn chair or blanket and tap your toes to the local live entertainment, and be sure to sample some of the excellent festival concession food.

One of the main draws of the festival is the Old Town Wine and Fine Arts Festival.  Come taste some of Virginia’s finest wines, and be sure to take a bottle or two of your favorites home.

After the festival, drive along Cedar Creek Grade, Barley Lane, Middle Road, and Marlboro Road to view the fragrant apple blossoms in front of the Blue Ridge Mountains

Winchester VA

Places outside of Town to Visit

Explore the Abrams Creek Wetlands Preserve

Just a 10-minute drive out of Winchester, you can enjoy a bit of nature at the 25-acre park that features marshes and swamps.  Bike or stroll along the mile-long interpretive trail observing the 300 different plants and see how many of the 180 species of birds you can spot. You may also spot muskrats, painted turtles, and mink if you are lucky.

Stroll through the Museum of the Shenandoah Valley

From Old Town, take a leisurely 30-minute walk or drive 5-minute to the Museum of the Shenandoah Valley, a wonderful Winchester tourist attraction.

At the Museum of the Shenandoah Valley, take time to explore the house, museum, and gardens. 

As you meander through the gardens, you will learn more about the region and its people.  The Asian-influenced water garden and the Glen Burnie Gardens are stunning.

The Shenandoah Valley, Founders, and R. Lee Taylor Miniatures Galleries on the museum’s second floor shouldn’t be overlooked. 

The Shenandoah Valley Gallery explores the history of the valley and includes changing exhibits of local decorate arts.

Impressive American and European decorative and fine arts are displayed in the Founders Gallery.

Discover the State Arboretum of Virginia, Blandy Experimental Farm

Take to the Virginia Native Plant Trail and paths throughout the 172-acre arboretum, where you will be at home with the 5,000 woody trees and shrubs from around the world.

Here you can view one-third of all the world’s species of pines, a grove of 300 ginkgo trees, a Lebanon allee, and explore the herb garden.

Shop at a Winchester Farm

Take a short scenic drive out of town for delicious fruit, fresh produce, and a sweet treat or two.

The Marker-Miller Orchards and Farm Market have an incredible on-site bakery where they make wonderful apple cider donuts. Before or after a snack, the kids will love playing on the playground.  You can even get a photo with the huge apple that is by the parking area.

The Homestead Farm at Fruit Hill Orchard, although smaller, has a beautiful organic garden, a gift shop, and delicious gluten and sugar-free baked goods.

Stop by and enjoy free bluegrass music on a Thursday evening between mid-August and early November.

Towards the end of September, Homestead Farm has a Sunflower Festival amongst their three acres of sunflowers.  Come out and enjoy the free music, entertainment, food, and crafts.

In town at the Taylor Pavilion, you will find things hopping each Saturday, May – September, at the Old Town Farmer’s Market.  Pick up fresh vegetables for dinner, local fruit for lunch, and incredible baked goods to eat as you enjoy the day.

Winchester VA

Where to Eat in Winchester Virginia

While in Winchester, eat at one or more of the excellent locally owned and operated restaurants in town.  Below are a few favorites.

During your stroll around the Pedestrian Mall, stop in at Oak Stone Pizza for a delicious brick oven pizza.  If you have a taste for fish and chips, stop in at Union Jack Pub and Restaurant, or for a romantic Italian dinner, visit Violino.

For a hearty breakfast of omelets, shrimp and grits, or their amazing biscuits and gravy, visit Bonnie’s Southern Kitchen and Bakery or Big L’s Bagels for a bacon, egg, and cheese everything bagel and a cup of coffee.  For those with time to sit and relax while enjoying their cup of coffee with a Cowbell buttermilk banana cake, then head to Hopscotch Coffee and Records.

When dessert is what you need, then order a Madagascar Vanilla Bean Cheesecake with caramelized bananas from Village Square Restaurant or head to Frenchies Frozen Yogurt Lounge for a cone or cup of refreshing frozen yogurt.

Local Craft Beer and Wineries to Visit

At the Pedestrian Mall, head to the second floor, where you will find ten of Alesatian Brewing Company’s craft beers on tap, ranging from amber, Belgian, and blonde ale to IPA and lagers.

Just down the street is the Winchester Brew Works, where they have 12 beers on tap, and you are welcome to bring your own food and sit either inside at the bar or outside on the pet-friendly patio.

After going to the Apple Blossom Festival, picking apples in the fall, or just passing all those apple orchards around Winchester, you may have a taste for cider.  Winchester Ciderworks produces six signature, English barrel-aged, and specialty ciders all from the local Frederick County apples at their Frederick Pike location.  Stop in and try one of their fermented apple drinks.

In the middle of the vineyards and apple orchards, you will find the James Charles Winery that the Bogaty family founded in 2015. Stop in and participate in the 30-minute Classic Tasting, where you get to enjoy all their currently available white and red wines.

They have Fire Pits throughout the winter months, where you can sit around and enjoying some James Charles wine.  For a romantic evening, reserve a 1-hour Table Experience where you will enjoy views of the Shenandoah Valley as you savor wines paired with spectacular food.

Winchester VA George Washington Hotel

Winchester VA Hotels

For the average family and travelers who just want a modest hotel room, the Sleep Inn and Suites Winchester and the SpringHill Suites Winchester are great options with complimentary breakfast and pools.

Around the corner from the pedestrian mall, the George Washington Hotel in the Georgian Revival brick building is both elegant and comfortable. The hotel offers a spa, saltwater pool, and an on-site restaurant and bar.

Ten miles east of town, the Historic Rosemont Manor offers luxury rooms on spectacularly manicured lawns.  If you stay here, be sure to go to one of their traditional English teas.

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