15 Best Things to Do in Winchester, VA

15 Best Things to Do in Winchester, VA


Less than a 2 hours’ drive away from Washington DC, the city of Winchester in Virginia is a beautiful combination of great food, drinks, art and history.

The city is full of happy vibes and offers something for people from all ages. Even though the city is not very big, it is a perfect destination for a weekend getaway or even a road trip.

The city is also famous for its museums and art stores which are located alongside restaurants serving hot and fresh food. The city also has its own breweries for people who lover freshly handcrafted drinks.

The ideal way to start your trip to exploring Winchester is to visit the Winchester visitor center that provides basic information about the city to all its visitors. Apart from that, this article will also help you in planning your trip in the best manner possible:

Shenandoah Valley Museum

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

The museum comprises of a building, Gardens spread over an area of 7 acres and a vintage home that was designed in the 18th century.

In addition to these, the museum has galleries having a great collection of art PCs, documents, maps, and other items belonging to the people of the area. A temporary exhibition displaying different collections at different times is also there in the museum.

Stonewall Jackson’s Headquarters

Stonewall Jackson’s Headquarters
Sarah Stierch, CC BY 4.0, via Wikimedia Commons


It is a historical building which was once used by the General of military as his headquarters. This place has a very Gothic and unique design as it is preserved and operated as a memorial tribute the military skills of general Stonewall Thomas.

It is believed that in 1860s had the largest 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 historical building.

Visit the Loudoun Street Pedestrian Mall

Loudoun Street Pedestrian mall
AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons


The pedestrian mall is not an average mall but an amalgamation of several restaurants, shops, museum, and other historically important buildings in the old town area of Winchester.

The place has been existing for more than 200 years and still brings immense pride to the city. It also has a museum dedicated entirely to the civil war at the end of the street.

The properly planned brick clad streets offer a splash pad for kids to play during the summer months. In addition, the small also host a large number of events every year, which include a special farmers market, Apple Blossom festivals, spring festival, etc. The museum has been on the National register of historic places.

Handley Regional Library

Handley regional library
AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons


The history of institutionalization of this library is as interesting as its interior and book collections. The library was started in order to fulfill the last wish of Judge John Handley and certainly named after him.

His will stated that a library for unlimited public use forever shall be opened. Following this, the library was opened in the year 1913 for the people of Winchester and continues to be a major attraction for the visitors of the city.

The interior of the library was designed in a manner to promote and suggest about open books. The dome of the building is made using glass entirely and provides a spell bounding view to the readers. The library has two wings which have awesome collection of books and offers books in each genre.

Mount Hebron Cemetery

Rouss tomb in Mount Hebron Cemetery
Steve Heap / Shutterstock.com


A cemetery might not come out to be a great choice for a getaway destination but this is not the case with Mount Hebron Cemetery. The cemetery is believed to be in existence since 1760s and has great historical value.

It has four different burying grounds, having the same entry. Various grounds have graves of people of great importance. For instance, the Stonewall Cemetery is believed to be dedicated entirely to the martyrs of the civil war and their families.

Around 2500 soldiers who lost their life during the civil war are rested here. In the other place, remains of a Lutheran Church are buried. The place also offers a labyrinth that allows quiet time for self-reflection.

Cedar Creek Historical Park


Made with the sole objective of preserving and protecting the historical and cultural richness of the city and the nearby areas.

The park has a location which is dedicated completely to the civil war battle of Cedar Creek. Another spot, the Belle Grove plantation is also quite famous touring spots among the visitors.

The place is known to offer various sort of historical and cultural programs for people on a regular basis. The park is an ideal location for people who are interested in history and military particularly.

Marker Miller Orchards and Farm Market

Marker Miller Orchard
Sarah Stierch, CC BY 4.0, via Wikimedia Commons


The Farm market is a perfect place for planning a simple yet fun outing with your family. The place offers a lot of different activities to be done by the visitors, with a beautiful setting having mountains and natural scenery in the background.

The best part about visiting this market is that you can get a container and then go for picking your own choice of produce from the Marker miller orchards.

The place also has ample arrangements for seating in form of picnic tables. You can also take your own food or purchase from the market, depending on your choice.

However, certain eatables like Fudge, Apple cider donuts, etc. are major catches and you should definitely give them a try.

Rinker Orchards


Rinker orchard is a very famous privately owned apple orchard in Winchester. Originally, the farm was used for growing crops, which was changed in the later stages.

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

Since then, the orchard is open for public visits and offers a lot of funny and apple gathering opportunity to the public. The farm is also famous for making its own natural Apple cider vinegar from its apple produce.

Apart from being a good place for family picnics, the place could also work as a great destination for romantic dates.

Sunflower Cottage


Sunflower cottage is an herb farm which is located at the front royal town. 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 producing beer and other drinks.

As much 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.

Backroom Brewery


The brewery got its name from its location which is also the reason the place is on this list. Located at the sunflower cottage farm, the Brewery is very famous for serving special beer.

The brewery produces its own beer from home grown ingredients. The drinks are made in small batches, due to which the taste of each drink from different batch is different. It also has a tasting room.

The brewery is also quite famous for its delicious snacks and food. The sandwiches and appetites served in the brewery are particularly famous for their unique taste and you should definitely give them a try.

Dinosaur Land

Dinosaur Land
Skvader, CC BY-SA 4.0, via Wikimedia Commons


Dinosaur land is a traditional place with no specific attractions and advanced technology, yet a famous place. The place has been developed with dinosaurs as the central theme.

Due to the theme, the place has around 50 dinosaur models which are perfectly managed and presented to the people. The place is a good place for chilling with kids as well as adults.

It also has a shop within the premises, that offers gifts related to dinosaurs and certain other items. The place has very reasonable prices and is definitely worth your money and time.

Drive-In Theatre

Family Drive in theatre
AgnosticPreachersKid, CC BY-SA 4.0, via Wikimedia Commons


This drive in theatre located near the Stephen’s city is one of the best things to do in the city of Winchester. Started in 1956, the family drive-in theatre is one of the only few drive-in theatres left in entire Virginia.

The theatre is owned by private parties and manages to have two screens for running the movies. The theatre has a unique way of making you nostalgic, sometimes by playing retro music and the other times by offering a playground for your kids.

You can watch two movies at once at this theatre, in an extremely budget friendly price. Even though the entire setting of the theatre is retro inspired, it uses the most advanced technology to deliver entertainment in best quality possible.

Rocking S. Ranch


This ranch, situated at the orchard road in Winchester is the place that offers a perfect out door experience for the residents of not only Winchester but the surrounding cities as well.

The place allows you to spend some time with horses enjoying activities such as horse-riding. You can also take horse riding lessons and explore the nearby trails located on the foot of the mountains and other areas nearby.  

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

The view around this place is beautiful and the ambience 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.

Abrams creek wetland preserves


Abrams creek wetland preserve is a place famous for offering a natural vacation destination to people. Ideal for picnicking, cycling, jogging, walking and even idly sitting, the place is just so rich in its natural content, it will take your heart away.

The place is surrounded by a wide range of wildlife species, providing habitat to animals as well as the birds in this same place. It also has a great variety of plants, which makes the creek a suitable place of someone interested in flora and fauna.

You can also take a guided tour to the creek to get a better idea about the variety of flora and fauna in the area or simply decide to keep it all to yourself without any professional guide.

Richard’s Fruit Market


Richard’s fruit market is another privately owned and managed fruit market in Winchester. The place is famous mainly because it has been in the family owning it for 5 generations.

They are known for selling their own produce of crops, fruits, vegetables and also meat, which is all produced and grown in their farms. The market is located at a scenic route and offers a visit to their flower garden where you can pick your own flowers.

You can visit their farms and visit the animals there. The apple grader is also open for public visits. Overall, the experience is one which you will definitely enjoy.

The city of Winchester is a place that offers diverse and dynamic activities to offer you, alongside a lot of historical and cultural lessons. From the breweries in the city to the parks and historical museums, everything is a bliss to your eyes as well as your curiosity ridden mind.

The vibrant environment and positive energy will soak up all your sorrows and negativity and give you an\ fresh perspective about things.
In addition to great cultural and historical variance, the city is also budget-friendly.

Due to being a famous tour location, the tickets to the museums, art galleries, food, drinks as well as accommodation can easily fit into everyone’s budget if planned properly.

The city has quite a number of unexplored places which you can discover while roaming around the beautiful and scenic streets. All this accounts to one surety, that your trip to Winchester will never be boring and futile, even if it is for the first time or for the hundredth time.