Things to Do in Winchester, VA

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If you're looking for small-town charm, Civil War history, and stunning mountain views, Winchester, VA is the place to be! Nestled in the beautiful Shenandoah Valley, this historic city has so much to offer. I found everything here, from museums and apple orchards to a lively downtown scene. Whether you're a history lover, foodie, or outdoor adventurer, I can tell you that Winchester is a hidden gem you won’t want to miss.

Best Time to Visit

In my experience, the best time to visit Winchester is in spring and fall (April–June and September–October). Spring brings the gorgeous blossoms and the famous Apple Blossom Festival, while fall offers crisp air and breathtaking foliage in the Shenandoah Valley. I’d say both seasons offer something special.

How to Get There

By Car: Winchester is conveniently located off I-81 and Route 50, about 90 minutes from Washington, D.C., and 2 hours from Baltimore. It’s a quick drive, and the scenic route is definitely worth it.
By Train: There are nearby Amtrak stations in Martinsburg, WV, and Harpers Ferry, WV, which are just a short drive to Winchester. I’ve found the train ride to be a pleasant way to get there.
By Air: If you’re flying in, Washington Dulles International Airport (IAD) is about an hour’s drive away. It’s an easy trip, and you’ll be in Winchester before you know it!

Where to Stay

The George Washington Hotel – If you're into vintage charm, this elegant downtown hotel is a must. With a spa and indoor pool, it’s the perfect mix of relaxation and history.
SpringHill Suites by Marriott – If you're traveling with family or planning a longer stay, this modern hotel with spacious suites is ideal.
Historic B&Bs – For a cozy, homey experience, I highly recommend staying in one of Winchester’s historic bed-and-breakfasts. You’ll enjoy a touch of Southern hospitality in these charming spots.