15 days in Winchester Itinerary

Created using Klarna Trips Winchester route planner
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Winchester
— 14 nights

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Winchester — 14 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Step off the beaten path and head to Rocking S Ranch and Museum of the Shenandoah Valley. Do some cultural sightseeing at National Shrine of St. Elizabeth Ann Seton and Rupp House. Get out of town with these interesting Winchester side-trips: Cedar Creek & Belle Grove National Historical Park (in Middletown), Skyline Caverns (in Front Royal) and Skydive Orange (in Orange). There's still lots to do: immerse yourself in nature at Fort Frederick State Park, contemplate the long history of Belle Grove Plantation, tour the pleasant surroundings at Stony Man Mountain Overlook, and grab your bike and head to Great Allegheny Passage.

To find photos, where to stay, maps, and other tourist information, read our Winchester trip itinerary planning website.

If you are flying in from South Africa, the closest major aiports are Washington Dulles International Airport, Ronald Reagan Washington National Airport and Joint Base Andrews. In September in Winchester, expect temperatures between 30°C during the day and 15°C at night.
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Parks · Historic Sites · Museums · Nature
Side Trips
Find places to stay Sep 12 — 26: