Things to do in Winchester
Explore thousands of activities with free cancellation and no added fees.
Design your experience with airport transfers, excursions, day tours & more.
Get an insider's look in what to book before you travel.
Discover the most popular places to visit in Winchester
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah University
Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Winchester Medical Center
Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.
Apple Blossom Mall
You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Rock Harbor Golf Course
Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savor the top-notch restaurants.
Winchester Little Theater
Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Discover the most popular landmarks and neighborhoods in Winchester
Old Town Winchester
Old Town Winchester is known for its ample dining options, and you can make a stop by Shenandoah Valley Discovery Museum and Bright Box Theater while in the area.