4 days in Western Maryland Itinerary

Kick off your visit on the 14th (Sun): steep yourself in history at Gordon-Roberts House, then sample the fine beverages at Charis Winery & Distillery, and then explore the landscape on two wheels at Great Allegheny Passage. Get ready for a full day of sightseeing on the 15th (Mon): try your luck at Rocky Gap Casino Resort, then immerse yourself in nature at Rocky Gap State Park, and then pick up some local products at Hill Top Fruit Market.

To see traveler tips, photos, where to stay, and tourist information, you can read our Cumberland journey planner.

New York City to Cumberland is an approximately 5-hour car ride. Expect little chillier evenings in Cumberland when traveling from New York City in August, with lows around 62°F. Finish your sightseeing early on the 15th (Mon) so you can drive to Oakland.

On the 16th (Tue), have fun and explore at The Discovery Center, contemplate the waterfront views at Deep Creek Lake State Park, then fly down the slopes at Wisp Resort, and finally stop by Bear Creek Trader's. Keep things going the next day: see the interesting displays at Garrett County Museum of Transportation, examine the collection at Garrett County Historical Museum, and then immerse yourself in nature at Swallow Falls State Park.

To see other places to visit and tourist information, read our Oakland trip builder tool.

You can drive from Cumberland to Oakland in 1.5 hours. Expect little chillier temperatures when traveling from Cumberland in August; daily highs in Oakland reach 72°F and lows reach 57°F. Finish your sightseeing early on the 17th (Wed) so you can drive back home.