Things to Do in Oakland, Maryland

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If you’re after small-town charm, mountain air, and a bit of that peaceful, off-the-grid magic—let me tell you about Oakland, Maryland. Nestled deep in the Allegheny Mountains, this town has become one of my favorite hidden gems in western Maryland. I’ve wandered its historic downtown, caught breathtaking lake views, and found more than a few scenic trails worth revisiting. Whether you're into vibrant fall foliage, farm-to-table flavors, or just want a place to slow down and breathe, Oakland delivers in the most welcoming way.

Best Time to Visit

I always recommend visiting between May and October. That’s when the weather’s mild, the festivals are in full swing, and the leaves turn into a kaleidoscope in fall. I’ve also visited in winter, and if you love skiing or want a cozy cabin weekend near Deep Creek Lake, it’s a fantastic time for snow sports and fireside relaxation.

How to Get There

By Car: I usually take U.S. Route 219—it’s a scenic drive whether you’re coming from D.C. (about 3 hours), Pittsburgh, or Morgantown (each about 2 hours). Just know, once you’re in the mountains, you’ll want to take your time and enjoy the views.
By Bus: Garrett Transit does offer some local service, but I’ve found it pretty limited—so if you can, bring your own wheels. It’s really the best way to explore the area.
By Train: There’s no direct Amtrak to Oakland, but if you don’t mind a little detour, the station in Cumberland (about an hour away) connects to the Capitol Limited route. I’ve done this and then rented a car from there—it worked out great for a weekend getaway.

Where to Stay

Oakland Motel: If you’re looking for a simple, affordable place close to everything, I’ve stayed here and appreciated how easy it made getting around town.
Inn at Deep Creek: This one’s perfect if you want that cozy, lodge-style feel right near the lake. I love that it’s only 15 minutes from Oakland but gives you those classic mountain vacation vibes—plus, the pool’s a nice bonus.
Haley Farm Inn and Retreat Center: I treated myself to a wellness weekend here once—and I’d do it again in a heartbeat. With spa treatments, mountain views, and rustic-chic rooms, it’s ideal for couples or anyone needing to reset and unwind.