Western Maryland trip planner
Create a fully customized day by day
itinerary for free
itinerary for free
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.
Create a full itinerary — for free!
Plan your trip to Western Maryland
- Get a personalized tripA full day by day itinerary based on your preferences
- Customize itRefine your trip. We'll find the
best routes and schedules
- Manage itEverything in one place. Everyone on the same page.
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 SharpsburgTrip planner Best for: Battlefield, Bridge, Cemetery HagerstownTrip planner Best for: Factory Outlet, Park, Art Museum BoonsboroTrip planner Best for: Cave, State Park, Gift & Specialty Shop
Popular things to do in Western Maryland
Historic Sites in Western Maryland
Nature in Western Maryland
Museums in Western Maryland
Shopping in Western Maryland
Recently planned trips to Western Maryland
4 days in Sharpsburg & Harpers Ferry BY A USER FROM UNITED STATES Sharpsburg Harpers Ferry 10 days in Maryland BY A USER FROM UNITED STATES Baltimore Ocean City Sharpsburg 21 days in United States BY A USER FROM UNITED STATES Cumberland Mill Run Wheeling 3 days in Knoxville BY A USER FROM UNITED STATES Burnside's Bridge Antietam National Battlefield Frog Eye Farm 5 days in Cumberland & Fayetteville BY A USER FROM UNITED STATES Cumberland Fayetteville 20 days in Maryland BY A USER FROM UNITED STATES Cumberland Hagerstown Baltimore