14 days in Winchester Itinerary

14 days in Winchester Itinerary

Created using Inspirock Winchester trip planner

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Winchester
— 13 nights

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Winchester

— 13 nights
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get outdoors at Little Washington Winery and Brewery and Devils Den. Museum-lovers will get to explore Museum of the Shenandoah Valley and Stonewall Jackson's Headquarters. Get out of town with these interesting Winchester side-trips: Sugarloaf Mountain (in Dickerson), Roads and Rails Museum (in Frederick) and R.H. Ballard Shop & Gallery (in Washington). Next up on the itinerary: wander the wide-open spaces of Rocking S Ranch, learn about all things military at United States Army Heritage and Education Center (USAHEC), tour the pleasant surroundings at Mary's Rock Summit Trail, and see the interesting displays at Seminary Ridge Museum and Education Center.

To see photos, maps, traveler tips, and other tourist information, refer to the Winchester online road trip planner.

In December, daytime highs in Winchester are 47°F, while nighttime lows are 31°F.

Things to do in Winchester

Museums · Parks · Nature · Outdoors

Side Trips