Things to do in Winchester

Activities, attractions and tours

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

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What to do in Winchester

Popular places to visit

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Museum of the Shenandoah Valley
Handley Regional Library

Handley Regional Library

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

Shenandoah University

Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah University

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

Shenandoah Valley Discovery Museum

4/5(1 review)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Rock Harbor Golf Course

Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savour the top-notch restaurants.

Rock Harbor Golf Course

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Patsy Cline Historic House

You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savour the top-notch restaurants.

Patsy Cline Historic House

Areas of Winchester

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Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Old Town Winchester
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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Winchester Historic District
Photo by KM Moore

Berryville

Frequently asked questions

Is Winchester worth visiting?
Winchester offers an interesting mix of culture, local charm and attractions. Whether you're into history, nature or traditional cuisine, there's a lot here to enjoy.
How do I spend a day in Winchester?
After you've visited leading attractions like Shenandoah Valley Discovery Museum and Abram's Delight, spend some time discovering Winchester's retail and dining scene.
What is the top tourist attraction in Winchester?
The top tourist attraction in Winchester is Shenandoah Valley Discovery Museum, so don't forget to put it on your sightseeing itinerary.
Is three days enough to stay in Winchester?
You can easily tick off leading sights like Shenandoah Valley Discovery Museum, Winchester Little Theatre and Abram's Delight with a three-day getaway in Winchester. On average, many travellers book two days here. There's plenty to experience nearby too, so stay a bit longer and check out Loudoun County.
Is Winchester a walkable city?
It all depends on what you'd like to see and do in Winchester. Several key attractions, such as Shenandoah Valley Discovery Museum and Winchester Little Theatre, are accessible on foot. If you're up for a stroll through some of Winchester's best neighbourhoods, Old Town Winchester is 0.16 kilometres away from downtown, while Winchester Historic District is 0.32 kilometres away from the city centre and also within walking distance.
What are some activities to do in Winchester with kids?
If you are after attractions and activities for all the family, here are some terrific ideas for what to do in Winchester with kids.
What to do in Winchester for adults?
There are lots of things to do in Winchester, with activities for adults of all ages. End the day with a visit to Valerie Hill Winery or Mt Hebron Cemetery.
Are there free things to do in Winchester?
One of the simplest ways to find free things to do in Winchester is to speak with a local tour guide. You'll get insider recommendations on exciting neighbourhoods, parks and other hotspots you can experience without reaching into your pocket. Mt Hebron Cemetery is one place that doesn't charge an admission fee.