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Western Maryland trip planner
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Western Maryland
Western Maryland tourism thrives on an alluring combination of history, scenery, outdoor adventure, and fabulous farm-to-table feasts. With a range of recreational options--from hiking, cycling, and rock climbing to skiing and whitewater rafting--thrill seeking travelers will have plenty on their plate. Charming visitors with its pedestrian-friendly downtown, Cumberland serves as a gateway into the region's rivers, forests, and mountains. Located near the site of one of the bloodiest single-day battles of the Civil War, the tiny town of Sharpsburg provides a glimpse into the region's poignant past. Home to a historic railroad station, Oakland also offers easy access to a major ski resort. Leisure travelers and pleasure seekers can take a scenic drive through Western Maryland wine country. Our United States online holiday planner allows you to plan your trip to Western Maryland and a wealth of other destinations big and small.
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Top Western Maryland tours
Places to visit in Western Maryland
CumberlandTrip planner
Best for: Historic Site, Biking Trail, State Park
OaklandTrip planner
Best for: State Park, Water Body, Waterskiing / Jetskiiing
HagerstownTrip planner
Best for: Factory Outlet, Park, Art Museum
SharpsburgTrip planner
Best for: Battlefield, Bridge, Cemetery
BoonsboroTrip planner
Best for: Cave, State Park, Gift & Specialty Shop
Museums in Western Maryland
See all ›Hidden gems in Western Maryland
Where to stay in Western Maryland

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Recently planned trips to Western Maryland
12 days in Western Maryland & Chicago
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Hagerstown
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Annapolis
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Knoxville
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Hagerstown
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Sharpsburg
Cumberland
2 days in Western Maryland
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Cumberland
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Hagerstown
Cumberland
Oakland
1 day in Western Maryland
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Cumberland
1 day in Western Maryland
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Cumberland
4 days in Western Maryland
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Cumberland
Oakland
5 days in Western Maryland
BY A USER FROM UNITED STATES
Oakland
Cumberland
Hagerstown