4 days in Western Maryland Itinerary

4 days in Western Maryland Itinerary

Created using Inspirock Western Maryland trip maker

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Route & dates

4 days in Western Maryland Itinerary

Start: Washington DC
Drive:  1 h 30 min
— 1 day
Drive:  1 h 30 min
— 3 nights
Drive:  2 h 30 min
End: Washington DC


Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. On the 2nd (Wed), witness the site of a historic battle at Antietam National Battlefield and then stop by Turn the Page Bookstore.

Plan a trip to Sharpsburg easily and quickly by telling Inspirock to suggest an itinerary.

Washington DC to Sharpsburg is an approximately 1.5- hour car ride. Traveling from Washington DC in October, expect little chillier with lows of 46°F in Sharpsburg. Finish your sightseeing early on the 2nd (Wed) so you can drive to Cumberland.

Things to do in Sharpsburg

Parks Historic Sites Nature

Side Trip

Turn the Page Bookstore
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Turn the Page Bookstore ©
Turn the Page Bookstore


Cumberland ©
Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. You'll explore the less-touristy side of things at Western Maryland Rail Trail and The Discovery Center. Get some cultural insight at Charis Winery and Gordon-Roberts House. Explore the numerous day-trip ideas around Cumberland: Oakland (The Oakland B&O Railroad Museum & Garrett County Museum of Transportation). There's still lots to do: explore the landscape on two wheels at Great Allegheny Passage, pick up some local products at Hill Top Fruit Market, tee off at Rocky Gap Golf Course, and try to win big at Rocky Gap Casino Resort.

To find more things to do, ratings, reviews, and more tourist information, you can read our Cumberland day trip tool.

Traveling by car from Sharpsburg to Cumberland takes 1.5 hours. October in Cumberland sees daily highs of 68°F and lows of 47°F at night. Cap off your sightseeing on the 5th (Sat) early enough to travel back home.

Things to do in Cumberland

Outdoors Trails Parks

Side Trips

Oakland, Flintstone, The Discovery Center, Western Maryland Rail Trail, Hill Top Fruit Market
Highlights from your plan
Charis Winery ©
Charis Winery
Gordon-Roberts House ©
Gordon-Roberts House
The Discovery Center ©
The Discovery Center