17 days in Winchester & Williamsburg Itinerary

17 days in Winchester & Williamsburg Itinerary

Created using Inspirock Virginia visit planner

This plan was created by another user.  Make it your plan

Route & dates

17 days in Winchester & Williamsburg Itinerary

Start: Winchester
— 13 nights
Drive:  3​h 30​min
— 3 nights
Drive:  3​h 30​min
End: Winchester


Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get outdoors at Antietam National Battlefield and Luray Caverns. Visit Gettysburg National Military Park and Harpers Ferry National Historical Park for their historical value. You'll find plenty of places to visit near Winchester: Gettysburg (Gettysburg National Cemetery, Jennie Wade House, & more), Shenandoah National Park (Skyline Drive & Old Rag Mountain Hike) and The Point (in Harpers Ferry). There's much more to do: explore the landscape on two wheels at Great Allegheny Passage, make a trip to Handley Regional Library, trek along Stony Man Mountain Hike, and explore the world behind art at Museum of the Shenandoah Valley.

To find traveler tips, photos, where to stay, and other tourist information, go to the Winchester day trip planning tool .

The Route module shows you travel options from your home to Winchester. In July, daytime highs in Winchester are 85°F, while nighttime lows are 65°F. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Williamsburg.

Things to do in Winchester

Parks Historic Sites Nature

Side Trips

Gettysburg, Shenandoah National Park, Luray, Harpers Ferry, Great Allegheny Passage
Highlights from your plan
Gettysburg National Military Park ©
Antietam National Battlefield ©
Antietam National Battlefield
Luray Caverns ©
Luray Caverns


Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
On the 22nd (Mon), steep yourself in history at Colonial Williamsburg, then steep yourself in history at Governor's Palace, then take in the architecture and atmosphere at Bruton Parish Episcopal Church, and finally look for gifts at The Peanut Shop of Williamsburg. Here are some ideas for day two: contemplate the long history of Historic Jamestowne, step aboard Jamestown Settlement, and then go on a hair-raising tour with a ghost and vampire tour.

To see traveler tips, where to stay, reviews, and other tourist information, refer to the Williamsburg day trip planning tool .

Traveling by car from Winchester to Williamsburg takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and train. Traveling from Winchester in July, things will get a bit warmer in Williamsburg: highs are around 91°F and lows about 73°F. Wrap up your sightseeing by early afternoon on the 24th (Wed) to allow enough time to drive back home.

Things to do in Williamsburg

Historic Sites Museums Parks
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Jamestown Settlement ©
Jamestown Settlement