10 days in Western Maryland Itinerary

10 days in Western Maryland Itinerary

Created using Inspirock Western Maryland tour itinerary maker

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Route & dates

10 days in Western Maryland Itinerary

Start: Washington DC
Drive:  1​h 30​min
1
Hagerstown
— 4 nights
Drive:  1​h 15​min
2
Cumberland
— 3 nights
Drive:  1​h 15​min
3
Oakland
— 2 nights
Drive:  3​h 15​min
End: Washington DC

4
nights
Hagerstown

Hagerstown ©
Hagerstown is a city in Washington County, Maryland, United States. Eschew the tourist crowds and head to C&O Canal National Historical Park and Train Room & Museum. Let the collections at Miller House Museum and Ferry Hill Plantation capture your imagination. You'll find plenty of places to visit near Hagerstown: Western Maryland Rail Trail (in Big Pool), Big Cork Vineyards (in Rohrersville) and Maryland Heights Trail (in Knoxville). There's much more to do: stroll the grounds of Rose Hill Cemetery, make a trip to Gen. Robert E. Lee's Headquarters Monument, steep yourself in history at Tolson's Chapel, and get engrossed in the history at Washington County Rural Heritage Museum.

For ratings, where to stay, and other tourist information, go to the Hagerstown online driving holiday planner .

Washington DC to Hagerstown is an approximately 1.5-hour car ride. Traveling from Washington DC in August, expect little chillier with lows of 65°F in Hagerstown. Finish your sightseeing early on the 6th (Tue) to allow enough time to drive to Cumberland.

Things to do in Hagerstown

Museums Parks Trails

Side Trips

Boonsboro, Sharpsburg, Big Cork Vineyards, Western Maryland Rail Trail, Maryland Heights Trail
Highlights from your plan
Hagerstown Roundhouse Museum ©
Hagerstown Roundhouse Museum
Tolson's Chapel ©
Tolson's Chapel

3
nights
Cumberland

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. Step off the beaten path and head to Rocky Gap Golf Course and Emmanuel Episcopal Church. Your inner history buff will appreciate Gordon-Roberts House and George Washington's Headquarters. Get out of town with these interesting Cumberland side-trips: Green Ridge State Forest (in Flintstone), House of Yoder (in Grantsville) and Fun Unlimited (in McHenry). There's still lots to do: do a tasting at Charis Winery, savor the flavors at Hill Top Fruit Market, and get lost in a book at Allegany County Library System - Washington Street Library.

To see other places to visit, maps, more things to do, and other tourist information, you can read our Cumberland trip planning tool .

Traveling by car from Hagerstown to Cumberland takes 1.5 hours. In August, daily temperatures in Cumberland can reach 84°F, while at night they dip to 62°F. Wrap up your sightseeing on the 9th (Fri) early enough to drive to Oakland.

Things to do in Cumberland

Outdoors Trails Parks

Side Trips

Flintstone, Grantsville, Fun Unlimited
Highlights from your plan
Green Ridge State Forest ©
Green Ridge State Forest
Gordon-Roberts House ©
Gordon-Roberts House
Emmanuel Episcopal Church ©
Emmanuel Episcopal Church

2
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. On the 10th (Sat), examine the collection at Garrett County Museum of Transportation, take an in-depth tour of The Oakland B&O Railroad Museum, then examine the collection at Garrett County Historical Museum, and finally play a few rounds at Lodestone Golf Course. Get ready for a full day of sightseeing on the next day: contemplate the waterfront views at Deep Creek Lake State Park, explore the engaging exhibits at The Discovery Center, and then trot along with a tour on horseback.

To find more things to do, where to stay, ratings, and more tourist information, go to the Oakland travel route planner.

Drive from Cumberland to Oakland in 1.5 hours. Traveling from Cumberland in August, things will get slightly colder in Oakland: highs are around 72°F and lows about 57°F. Finish your sightseeing early on the 11th (Sun) to allow enough time to travel back home.

Things to do in Oakland

Outdoors Museums Golf

Side Trip

The Discovery Center
Highlights from your plan
Lodestone Golf Course ©
Lodestone Golf Course
Deep Creek Lake State Park ©
Deep Creek Lake State Park
The Discovery Center ©
The Discovery Center