5 days in Western Maryland Itinerary

5 days in Western Maryland Itinerary

Created using Inspirock Western Maryland trip itinerary planner

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Make it your trip
Drive
1
Cumberland
— 2 nights
Drive
2
Oakland
— 2 nights
Drive

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Cumberland

— 2 nights
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. Visit Gordon-Roberts House and Paw Paw Tunnel for their historical value. Take a break from the city and head to Cheat Lake Trail and Green Ridge State Forest. Change things up with a short trip to Western Maryland Rail Trail in Big Pool (about 50 minutes away). There's more to do: do a tasting at Charis Winery & Distillery and grab your bike and head to Great Allegheny Passage.

To find reviews, more things to do, photos, and more tourist information, read Cumberland route planner.

New York City to Cumberland is an approximately 5-hour car ride. You can also do a combination of car and flight. In May in Cumberland, expect temperatures between 74°F during the day and 52°F at night. Cap off your sightseeing on the 20th (Thu) early enough to go by car to Oakland.

Things to do in Cumberland

Trails · Parks · Outdoors · Nature

Side Trips

Oakland

— 2 nights
Oakland is a town in the west-central part of Garrett County, Maryland. On the 21st (Fri), examine the collection at Garrett County Historical Museum, then get engrossed in the history at The Oakland B&O Railroad Museum, and then immerse yourself in nature at Cathedral State Park.

To find more things to do, maps, and other tourist information, go to the Oakland road trip app.

You can drive from Cumberland to Oakland in 1.5 hours. Traveling from Cumberland in May, expect Oakland to be little chillier, temps between 63°F and 47°F. Wrap up your sightseeing on the 22nd (Sat) to allow time to travel back home.

Things to do in Oakland

Parks · Nature · Museums

Side Trip