Blake Walsh

25 Best Things to Do in Winchester, VA

  • Published 2023/04/11

Less than a two-hour drive from Washington DC, the city of Winchester in Virginia is a beautiful combination of great food, drinks, art and history.

This vibrant city offers diverse and dynamic activities alongside many historical and cultural lessons.

From breweries to parks and historical museums, everything in this city will be bliss to your eyes and your curiosity-ridden mind.

Winchester has quite a number of unexplored places that you can discover while roaming around its beautiful and scenic streets.

All this accounts for one surety: your trip to Winchester will never be boring or futile, whether it is your first or your hundredth time.

These are the best things to do in Winchester, Virginia:

Learn about the Local History at the Museum of the Shenandoah Valley

Exterior of the Shenandoah Valley Museum

Steve Heap /

This beautiful museum in the city of Winchester is known for preserving the history and culture of the Shenandoah Valley and its people.

The museum comprises a building, gardens spread over an area of seven acres, and a vintage home that was designed in the 18th century.

In addition, the museum has galleries with a great collection of art, documents, maps, and other items belonging to the people of the area.

A temporary exhibition displaying different collections at different times is also available in the museum.

Step Back in Time at the Stonewall Jackson’s Headquarters Museum

Exterior of Stonewall Jackson’s Headquarters

Sarah Stierch, CC BY 4.0, via Wikimedia Commons

The Stonewall Jackson’s Headquarters Museum is a historic building that was once used by General “Stonewall” Thomas Jackson as his headquarters.

This place has a Gothic and unique design as it is preserved and operated as a memorial tribute to the general’s military skills.

It is believed that in the 1860s, the museum had the most extensive collection of military weapons and items from various soldiers and staff members.

Some significant items like prayer tables and family pictures are still preserved and available in this historic building.

Visit Winchester’s Famous Loudoun Street Pedestrian Mall

People walking along Loudoun Street Pedestrian mall

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

The Loudoun Street Pedestrian Mall is not an average mall but an amalgamation of several restaurants, shops, a museum, and other historically important buildings.

Situated in Winchester’s old town area, the place has existed for more than 200 years and still brings immense pride to the city.

Buildings of Loudoun Street Pedestrian Mall

APK, CC BY-SA 4.0, via Wikimedia Commons

The Shenandoah Valley Civil War Museum is located at the end of the street.

The properly planned brick-clad streets also offer a splash pad for kids to play during the summer months.

In addition, the mall also hosts a large number of events every year, which include a special farmers’ market, apple blossom festivals, a spring festival, and more.

Night scene at Loudoun Street Pedestrian Mall

Fuzzykittenhead, CC BY 3.0, via Wikimedia Commons

Browse through the Books at Handley Regional Library

Exterior of Handley regional library

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

The history of this library’s institutionalization is as fascinating as its interior and book collections.

Handley Regional Library was started to fulfill the last wish of Judge John Handley and is named after him.

According to his will, Handley stated that he would like to build a library that would always be open for public use.

Interior of Handley Regional Library

Sarah Stierch, CC BY 4.0, via Wikimedia Commons

Following this, the library was opened for the people of Winchester in 1913 and continues to be a significant attraction for the city’s visitors.

Its interior was designed in a manner to promote open books.

The dome of the building is made entirely using glass and provides a spellbinding view to readers.

Handley Regional Library has two wings with a fantastic collection of books in various genres.

View of Handley Regional Library's stained glass dome

Acroterion, CC BY-SA 3.0, via Wikimedia Commons

Pay Your Respects at Mount Hebron Cemetery

Rouss tomb in Mount Hebron Cemetery

Steve Heap /

A cemetery might not be the kind of attraction you’d want to add to your itinerary, but this won’t be the case with Mount Hebron Cemetery.

The cemetery is believed to have existed since the 1760s and has great historical value.

It has four different burying grounds with the same entry.

Various grounds are home to graves of people of great importance.

Entrance to the Mount Hebron Cemetery

Sarah Stierch, CC BY 4.0, via Wikimedia Commons

For instance, Stonewall Confederate Cemetery is dedicated entirely to the martyrs of the Civil War and their families.

Around 2,500 soldiers who lost their lives during the Civil War are buried here.

In the other place, the remains of a Lutheran Church are buried.

The place also offers a labyrinth that allows quiet time for self-reflection.

Grave of Christian Streit at Mount Hebron Cemetery

Sarah Stierch, CC BY 4.0, via Wikimedia Commons

Pick Your Own Produce at Marker-Miller Orchards Farm Market

The trees of Marker Miller Orchard

Sarah Stierch, CC BY 4.0, via Wikimedia Commons

Marker-Miller Orchards Farm Market is a perfect place for planning a simple yet fun outing with your family.

The place offers many different activities to be done by visitors, with beautiful mountains and natural scenery in the background.

The best part about visiting this market is that you can get a container and pick your own produce from the orchards.

The place also has ample arrangements for seating in the form of picnic tables.

Depending on your choice, you can bring your own meals or purchase food from the market.

However, certain snacks like fudge and apple cider donuts are popular among visitors, and you should definitely give them a try.

Go Horseback Riding at the Rocking S. Ranch

The Rocking S. Ranch, situated on Orchard Road, is the place that offers a perfect outdoor experience for residents of Winchester and its surrounding cities.

The place allows you to spend some time with horses and enjoy activities like horseback riding.

You can also take horseback riding lessons and explore the nearby trails located on the foot of the mountains and other nearby areas.

Along with that, you can also spend some leisure time with friends and family in this ranch’s natural setting.

The view around this place is beautiful, and the ambiance is soothing, which provides immense joy.

Being accessible from all the nearby towns, the place is quite busy but is definitely worth visiting on your trip to Winchester.

Meet the Wildlife at the Abrams Creek Wetlands Preserve

The Abrams Creek Wetlands Preserve is a famous natural vacation destination.

Ideal for picnicking, cycling, jogging, walking and even idly sitting, the place is just so rich in its natural content that it will take your heart away.

The place is surrounded by a wide range of wildlife species, as it is filled with their natural habitats.

It also has a great variety of plants, which makes the Abrams Creek Wetlands Preserve a suitable place for those interested in flora and fauna.

You can also take a guided tour of the preserve to better understand the variety of flora and fauna in the area.

Alternatively, you can explore the preserve on your own.

Participate in Outdoor Activities at Jim Barnett Park

Over 170 acres of lovely green space can be found in Jim Barnett Park, while more than 100 acres of park property are situated inside Winchester’s residential areas.

Numerous park amenities, such as the social hall, meeting rooms, gym, pavilions, tennis courts, and ball fields, are available for rent.

The indoor pool at Jim Barnett Park features six 25-meter lanes and is accessible all year.

Visitors and residents can play the 18-hole disc golf course at Jim Barnett Park, and if requested, discs can be loaned at the Rec Center.

Additionally, Jim Barnett Park is home to trails that include the Sensory Trail, Kiwanis Par Course, and Winchester Green Circle Trail.

Select from a wide variety of activities available at Jim Barnett Park, and you’ll undoubtedly depart with a smile after making unforgettable memories here.

Enjoy a Cider at Winchester Ciderworks

Unmatched hard cider is available at Winchester Ciderworks, and they’re sure to be unlike most you’ve ever had.

The tasting room was built on a foundation established in 1900, and until it was transformed into an apple cold storage facility in 1946, the structure was used as an orchardists’ barn for many years.

Using apples from Frederick County, the cider is internally pressed, fermented, and bottled.

Before any of their ciders are made available for drinking, they are brewed for at least a year.

Once served at cellar temperature, their distinctive eastern English style off-dry ciders are incredibly delightful.

Savor outstanding cider at Winchester Ciderworks with family and friends.

Watch a Performance at Bright Box Theater

Bright Box Theater is a vibrant performance and event space situated in the Loudoun Pedestrian Mall in the heart of Winchester.

Thousands of locals and tourists have come to this theater, making it the pulsing core of Winchester’s downtown area.

Bright Box Theater has staged hundreds of performances since it opened in May 2013, including drag shows, jazz, punk, reggae, rock, comedy, jam bands, and private parties with complex themes.

Modern sound, lighting, and display systems may be found in the magnificent Bright Box Theater.

It is an excellent location for weddings, private events, gatherings, and fundraisers, in addition to hosting some of the most outstanding musical and comedic performances in the neighborhood.

The theater has received recognition and several awards from publications, including The Winchester Star and Virginia Living Magazine.

Have a Snack with Friends at Roma Old Town Wood-Fired Pizzeria

Roma Old Town Wood-Fired Pizzeria is a popular hangout for locals on Winchester’s historic Loudoun Pedestrian Mall.

The restaurant upholds the standards of Roma Casual Italian and Greek in terms of uniqueness, freshness, and value.

Their wood-fired brick oven elevates the flavors of their handcrafted pizza, and their unmatched range of beers guarantees the ideal pairing for your meal.

The pizzeria also serves delicious salads, fresh and plentiful appetizers bursting with Mediterranean flavor, and classic favorite Roma Casual Italian and Greek entrées.

Tourists and locals come together at Roma Old Town Wood-Fired Pizzeria, which boasts a welcoming social setting where you can enjoy a tasty meal.

Visit and Learn History at the Kernstown Battlefield and the Pritchard-Grim Farm

History marker of Kernstown Battlefield

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

An 1854 home, a visitor center, and a 388-acre Civil War battlefield park are all featured at this popular tourist site.

Follow the walking pathways on the Kernstown Battlefield to learn more about what happened during the battles of Kernstown.

You may tour the battlefield’s visitor center to understand more about the history.

Moreover, the Pritchard House is where the descendants of Samuel and Helen Pritchard hid in the cellar while waiting for peace to return to the Pritchard-Grimm Farm.

The 1854 house has witnessed the victories, the setbacks, the pleasures, and the tears of the families that have lived there.

The Kernstown Battlefield and the Pritchard-Grim Farm in Winchester are truly rich in history.

Enjoy Some Alone Time at Shawnee Springs Preserve

Shawnee Springs Preserve is one of the best places in Winchester to be in tune with yourself and with Mother Earth.

The trail here is called a “Healing Trail” because of the serene beauty of the preserve that features thickets of greenery that blend well together.

Trekking here isn’t too difficult as well, especially since the trial isn’t long and there are no major elevation changes.

You’ll experience a gentle creek here along with an abundance of different plant life and wildlife; bringing your dogs here is good for their exercise.

Shawnee Springs Preserve can be found along Hollingsworth Drive where the trail begins.

Try the Coffee at Hopscotch Coffee and Records

If you’re planning to go to Shawnee Springs Preserve, Hopscotch Coffee and Records is just a stone’s throw away that’s sure to enamor you.

Known for their delicious coffee and additional record store, this place leans more to the attractions that only locals are familiar about.

The atmosphere here is one of the best places to enjoy a warm cup of coffee, as it’s both inviting yet tranquil at the same time.

Both the interiors and the exteriors are Instagram-worthy, with their showstopper being a huge collection of records displayed by their counter.

With its vintage aesthetic and highly rated coffee, many locals believe that Hopscotch Coffee and Records is the best cafe in the city.

Tour the Patsy Cline Historic House

Exterior of Patsy Cline Historic House

Mlsmith1962, CC BY-SA 4.0, via Wikimedia Commons

Patsy Cline is one of the most iconic country and pop musicians from the 20th Century, known for her catchy romance songs and soothing voice.

Whether you’re a fan of her music or history, Patsy Cline Historic House is one of the unique things you can experience in Winchester.

Her house dates back to the late 1940s, and has since been preserved to become a tourist destination that’s available for tours.

You can see tons of her photographs and everyday items, and the tour guides here will definitely accentuate the experience through their knowledge and friendliness.

Only a small house but packed with tons of history, Patsy Cline Historic House is a great addition to your itinerary.

Find it along South Kent Street once you’ve booked an appointment for a tour.

Go Drinking with Friends at Oak Stone Craft Pizza and Bar

One of the best places to chow down at Winchester is at Oak Stone Craft Pizza and Bar—it’s arguably one of the best local restaurants in the city.

You can drop by here for lunch if you’re feeling famished with friends and family, as they have huge pizzas and other viands like wings that are great for sharing.

However, the atmosphere here truly lights up during night, when the place becomes much livelier because of their fame for alcoholic beverages as well.

Lots of cocktails here go well with their savory and flavor-packed food, and they have happy hour to boot.

Both a relaxed and a visually inviting place with good food, don’t miss out on Oak Stone Craft Pizza and Bar along Valley Avenue.

Catch a Musical at Ohrstrom-Bryant Theatre

Far view of Ohrstrom-Bryant Theatre

Steve Heap /

Ohrstrom Bryant Theatre is just a stone’s throw away from Jim Barnett Park, making this a convenient stopover.

It’s a modern facility where you can catch the up and coming live performances of many musical groups in Winchester.

With clean and vibrant facilities, the tickets here are worth it—it’s great for families who are into performance arts.

Managed by the Shenandoah University, Ohrstrom-Bryant Theatre features many events that also include the students, making this a staple among the locals.

Ohrstrom-Bryant Theatre is a great addition if you have some extra time in Winchester, or if you’re all about musicals in the first place.

Exterior of Ohrstrom-Bryant Theatre

Steve Heap /

Other Things to Do Nearby

Take a Side Trip to Cedar Creek Historical Park

Exterior of the Belle Grove manor house at Cedar Creek Historical Park

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

Situated 20 minutes away from Winchester, Cedar Creek Historical Park was built with the sole objective of preserving and protecting the historical and cultural richness of the city and its nearby areas.

The park has a location that is dedicated entirely to the civil war battle of Cedar Creek.

Scenic view from the Belle Grove manor house at Cedar Creek Historical Park

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

Another spot called Belle Grove Plantation is also quite famous among tourists.

The place is known to offer various historical and cultural programs for people on a regular basis.

The park is an ideal location for those who are particularly interested in history and the military.

The battlefield of Cedar Creek Historical Park

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

Enjoy Fresh Apple Products at Rinker Orchards

Rinker Orchards is a famous privately-owned apple orchard in Stephens City, which is a 15-minute drive away from Winchester.

Initially, the farm was used for growing crops.

The family decided to convert the entire property into an apple orchard, which turned out to be one of the first pick-your-own apple orchards in the state.

Since then, the orchard has been open for public visits and offers many funny and apple gathering opportunities to the public.

The farm is also famous for making its own natural apple cider vinegar with its apple produce.

Apart from being an excellent spot for family picnics, the place can also work as a great destination for romantic dates.

Visit Middleton’s Popular Sunflower Cottage

Sunflower Cottage is an herb farm located in Middletown.

Just 20 minutes outside Winchester, the cottage is famous as it grows an annual field of more than 120,000 herbs and other plants throughout the year.

More than 20 acres of the land is dedicated to producing hop, which is further used in making beer and other drinks.

As many as 20 different types of beers are produced using this hop.

Even though the farm is open for visits throughout the year, it is especially busy and beautiful during the fall season.

Sample the Beers at Backroom Brewery

Located at the Sunflower Cottage farm, Backroom Brewery is very famous for serving special beer.

The brewery produces its own beer, which is prepared with homegrown ingredients in small batches.

Backroom Brewery has a tasting room where guests can sample their handcrafted brews.

The brewery is also quite famous for its delicious snacks and food.

The sandwiches and appetites served here are particularly famous for their unique flavors, and you should definitely give them a try.

Bring Your Kids to Dinosaur Land

Dinosaur sculptures at Dinosaur Land

Skvader, CC BY-SA 4.0, via Wikimedia Commons

A theme park located 15 minutes outside Winchester, Dinosaur Land is one of the most popular attractions in White Post.

The place has been developed with dinosaurs as its central theme.

Dinosaur Land has around 50 dinosaur models, which are perfectly managed and presented to the people.

Welcome sign of Dinosaur Land

Skvader, CC BY-SA 4.0, via Wikimedia Commons

It’s a great place to visit with kids as well as adults.

The theme park also has a shop within the premises where you can shop for dinosaur-themed gifts and souvenirs.

The place has very reasonable prices and is definitely worth your money and time.

Catch a Film at The Family Drive-In Theatre

Daytime view of the Family Drive in theatre

AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons

The Family Drive-In Theatre, located in Stephens City, is one of the best things to do when you’re in the vicinity.

Started in 1956, it is one of the only few remaining drive-in theaters in the entire state of Virginia.

The theater is owned by private parties and has two screens for running the movies.

The Family Drive-In Theatre has a unique way of making you nostalgic, sometimes by playing retro music and the other times by offering a playground for kids.

You can watch two movies at once at this theater at a very budget-friendly price.

Even though the entire setting of the theater is retro-inspired, it uses the most advanced technology to deliver entertainment in the best quality possible.

Shop for Fresh Produce at Richard’s Fruit Market

Richard’s Fruit Market is a privately owned and managed fruit market in Stephens City.

The place is famous mainly because it has been owned and operated by the same family for five generations.

They are known for selling their own crops, fruits, vegetables, and meat, which are all produced and grown on their farms.

Richard’s Fruit Market is located on a scenic route and offers a visit to their flower garden where you can pick your own flowers.

You can also visit their farms and meet the animals there.

The apple grader is also open for public visits.

Overall, Richard’s Fruit Market offers an experience that you will definitely enjoy.

Final Thoughts

In Winchester, Virginia, you may engage in both indoor and outdoor activities throughout the day.

You will undoubtedly want to explore its many renowned eateries, museums, historical sites, and popular tourist spots.

Overall, a visit to Winchester is unforgettable because of its beautiful scenery, historical significance, and distinctive attractions.

Use this list of the best things to do in Winchester and start planning your trip today!

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