Looking for a scenic mountain escape filled with charm, history, and fresh-air adventures? I think you’ll love Cumberland! I’ve wandered its historic streets, biked along the C&O Canal, and soaked up those Allegheny Mountain views—and I can tell you, it’s the kind of place that feels both peaceful and full of possibilities. Whether you’re into hiking, riverside picnics, or just taking a slow stroll downtown, Cumberland offers that perfect mix of small-town warmth and big outdoor energy.

Best Time to Visit

If you ask me, the best times to visit are in the spring and fall (April–June and September–October). That’s when the weather’s perfect for long hikes and bike rides, and the mountain scenery really shines. I love catching the fall colors or arriving just in time for one of the town’s laid-back local festivals.

How to Get There

  • By Car: I usually drive in along I-68—it’s about 2 hours from Pittsburgh or 2.5 from D.C., and honestly, it’s a beautiful drive.
  • By Train: Amtrak’s Capitol Limited line is a great way to get here—I’ve taken it from D.C., and the mountain views along the way are worth the ride alone.
  • By Plane: If you’re flying, I’d suggest landing in Pittsburgh or Dulles. From there, you’ll have about a 2–2.5 hour drive through rolling hills and quiet countryside.

Where to Stay

  • Fairfield Inn & Suites Cumberland – I’ve stayed here before—it’s super comfy and just steps from the C&O Canal towpath and downtown’s artsy spots. You’ll be close to everything.
  • Rocky Gap Casino Resort – If you’re up for more of a getaway vibe, this lakeside resort is a great pick. I’ve enjoyed the spa and trails at Rocky Gap State Park, and you might just get hooked on the lake views and golf course.

Best Things to Do in Cumberland, MD

Bike or Hike Scenic Wonders on the Great Allegheny Passage

Leart/stock.adobe.com

Bike or Hike Scenic Wonders on the Great Allegheny Passage -                                    

Escape to Nature’s Playground at Rocky Gap State Park

Oleksii Sergieiev/stock.adobe.com

Escape to Nature’s Playground at Rocky Gap State Park -                                    

Journey Through History in the C&O Canal’s Paw Paw Tunnel

Lydia/stock.adobe.com

Journey Through History in the C&O Canal’s Paw Paw Tunnel -                                    

Ride Through Time on the Western Maryland Scenic Railroad

evannovostro/stock.adobe.com

Ride Through Time on the Western Maryland Scenic Railroad -                                    

If You Love History and Heritage, Stop by the C&O Canal National Historical Park

Zack Frank/stock.adobe.com

If You Love History and Heritage, Stop by the C&O Canal National Historical Park -  

Explore Local Stories at the Allegany Museum

Allegany Museum

Explore Local Stories at the Allegany Museum -  

Step Into the Past at George Washington’s Headquarters

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Step Into the Past at George Washington’s Headquarters -                                    

Marvel at Natural Beauty in the Cumberland Narrows

den-belitsky/stock.adobe.com

Marvel at Natural Beauty in the Cumberland Narrows -                                    

If You’re Ready for Classic Fun, Head to the Allegany Fairgrounds

Allegany Fairgrounds

If You’re Ready for Classic Fun, Head to the Allegany Fairgrounds -  

In Summary...

(and if you want to revisit my photo journey)