5 days in Winchester Itinerary

5 days in Winchester Itinerary

Created using Inspirock Winchester travel route maker

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

Route & dates

View / edit route

— 4 nights


Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Take a break from the city and head to Antietam National Battlefield and Luray Caverns. Popular historic sites such as Harpers Ferry National Historical Park and Patsy Cline Historic House are in your itinerary. Change things up with these side-trips from Winchester: Hollywood Casino at Charles Town Races (in Charles Town), Gettysburg National Military Park (in Gettysburg) and Copper Fox Distillery (in Sperryville). There's much more to do: explore and take pictures at Skyline Drive, look for gifts at My Neighbor and Me, and get lost in a book at Handley Regional Library.

For other places to visit, traveler tips, ratings, and other tourist information, you can read our Winchester trip planning tool .

In July, plan for daily highs up to 85°F, and evening lows to 65°F. Cap off your sightseeing on the 2nd (Fri) early enough to travel back home.

Things to do in Winchester

Parks Nature Historic Sites

Side Trips

My Neighbor and Me, Antietam National Battlefield, Copper Fox Distillery, Harpers Ferry National Historical Park, Skyline Drive
Highlights from your plan
Gettysburg National Military Park ©
Gettysburg National Military Park
Antietam National Battlefield ©
Antietam National Battlefield