Things to do & places to visit in Cumberland, Maryland, United States

At the base of the Appalachian Mountains in Allegany County, Maryland, the city of Cumberland has been a military outpost manned by George Washington, a shipping hub, a manufacturing capital and "The Gateway to the West." Head to the Cumberland Gap National Historical Park and explore the same paths taken by early American pioneers. A ride on the Western Maryland Scenic Railroad carries visitors back to the golden age of rail, chugging past stunning mountain scenery in vintage train cars.

Cumberland city in Maryland, United States. Timezone: America/New_York, current date and time: Sunday, May 12, 2024, 4:23.

Top things to do (24)

Top places to visit (30 attractions) view more »

5.0 Great Allegheny Passage (248 reviews)
- GAP and C&O bicycle touring adventure
Sunday: 12:00 AM - 11:59 PM Spent More than 3 hours Biking Trails • Hiking Trails

The Great Allegheny Passage soars over valleys, snakes around mountains, and skirts alongside three rolling rivers on its nearly level path from Cumberland, Md. to Pittsburgh. Cyclists pass through the Cumberland Narrows, cross the Mason-Dixon Line, top the Eastern Continental Divide, wind their way through Pennsylvania’s breathtaking Laurel Highlands, journey through the region’s coke, coal, mining, and steel-making corridor, and end at Pittsburgh’s majestic Point State Park. Stunning views of waterfalls, gorges, river valleys, and farmland are everywhere, especially from outside the Big Savage Tunnel, from the sweeping Salisbury Viaduct, at both ends of the Pinkerton Tunnel, and via the Ohiopyle High and Low Bridges. Riders overlook the joining of rivers at Confluence, McKeesport, and Pittsburgh, and can explore adjoining peninsulas, state parks, hollows, wildflower stands, and forests on foot at many places along the trail. See more..
5.0 Exit Strategy Escape Room (12 reviews)
- Untouchables Room - Lots of fun!
Sunday: Escape Games

Downtown Cumberland's premier escape room adventure. 3 themes available; The Untouchables, Through the Looking Glass, and The Cursed Treasure. You'll have 60 minutes to solve the room, find clues, leads and solving puzzles to unlock the locks and make your escape! Located on the 3rd floor of the Allegany Museum building. Sister company to Get Out & Play! Outfitters See more..
5.0 Allegany County Library System - Washington Street Library (6 reviews)
- Has a Maryland Room on 2nd floor for historical research
Sunday: Libraries

Books, movies, internet access, color printing, community connections, Story Hour, WiFi, eBooks, free streaming services. See more..
5.0 Dig Deep Brewing Company (5 reviews)
- Get the flight of your choice!
Sunday: 1:00 PM - 6:00 PM Breweries

Dig Deep Brewing Company, located in the historic Footer Dye Works Building, was started in Cumberland, Maryland in 2017. We established this brewery to live out our passion and our motto: Whatever You Dig, Dig Deep! See more..
5.0 Allegany County Library System - South Cumberland Library (5 reviews)
- Great Staff
Sunday: Libraries

Books, movies, internet access, color printing, community connections, Story Hour, WiFi, eBooks, free streaming services. See more..
5.0 Cumberland Narrows (4 reviews)
- awesome
Geologic Formations

Dominating the skyline of Cumberland to the north and west is "The gateway to the west." Route 40, two railroads, and Will's Creek pass through between Haystack Mountain to the South, and Will's Mountain to the North. There is a rock outcropping on Will's Mountain, that, legend has it, a couple leaped to their death, because they could not marry. Will's Creek has cut down through more than 600 feet of limestone to create the path. On Haystack Mountain side, access can be had from I-68 west at Sunset Drive. Just park and keep walking north/east to the edge. One the Will's mountain side, There is a steep road to the top, but it is private and gated. It's a challenging hike. Some of the property is private, and some is a designated state park. Back at the turn of the 19th Century, the Will's Mountain Inn was a popular get-away destination. See more..
5.0 Cumberland Theatre (4 reviews)
- Outstanding talent
Spent 1-2 hours Theaters

The Cumberland Theatre is Western Maryland's only regional professional theatre presenting musicals, comedies and dramas throughout the year and also serves as a performance venue for other non-profit arts organizations throughout the region. See more..
5.0 F. Brooke Whiting House and Museum (2 reviews)
- Amazing Collection
Spent 1-2 hours Art Museums
Hidden gem of a museum! Evan gave us an enjoyable, leisurely detailed tour of Whiting's fascinating finds & multi-generational heirlooms from all over the world. English, Asian, literary and American antiques ... all beautifully displayed in this deceptively spacious 1911 home, just a few blocks from the Gordon-Roberts House. Ancient & contemporary artwork, pottery, transfer-ware, glassware, Murano fixtures, miniature portraits, Tiffany pieces, and a dizzying comprehensive book collection by Whiting, who was curator at a university library. Shown by appointment, really worth it. Thank you, Evan & Lindsay, for making us most welcome. See more..
5.0 Windsor Castle Events Centre (1 review)
- Wonderful for Weddings
Spent 2-3 hours Convention Centers

My son's wedding was held here. More than enough room for 200 people, a bar set up, cake and gift area and appetizers. Spacious dance floor, room for DJ and room for a grand entrance. A small seating area with couches for more comfortable conversations. Small rooms to meet upstairs, bathrooms large and clean and some parking next to the Centre. See more..
5.0 Allegany Arts Council (1 review)
- Excellent
Sunday: 11:00 AM - 5:00 PM Spent < 1 hour Art Galleries
Amazing art gallery with event and meeting rooms and a room upstairs for parties and small weddings. There is usually always something going on here. Lots of great talent is show caed and they offer many classes and events for children and artists of all ages. You owe it to yourself to check it out. See more..
4.5 Rocky Gap State Park (221 reviews)
- A Day at the Beach
State Parks

Park that offers swimming beaches, campsites and boat rentals. See more..
4.5 C&O Canal - Paw Paw Tunnel (208 reviews)
- Bring your headlamps!
Historic Sites

So first: the area is under construction due to landslides which means that you can enter and walk through the tunnel but that you have to turn around and walk back out the way you came instead of continuing on to the trail. I really enjoyed this tunnel and this hike. I had a headlamp in preparation. I couldn't imagine doing this hike without some type of light. It's a unique experience inside as it feels like you're in a cave walking along the path. There are mushrooms growing and even some water dripping throughout. The floor is a bit uneven, so be careful with that. Once you leave the tunnel the way you came there is a trail that goes up the side and goes over the tunnel and back towards the campground parking lot. Some nice views from up there too! I would definitely recommend this hike. See more..
4.5 C&O Canal National Historical Park and Visitors Museum (193 reviews)
- Excellent biking path with the right kind of bike
Sunday: 9:00 AM - 5:00 AM Visitor Centers

Biked around 8 miles out then back around Oldtown just before Memorial Day, separate review of Paw Paw tunnel area. The towpath was wet in spots and is best for a hybrid or mountain bike, though a road bike probably would be OK. Great contrast with the very smooth Great Allegheny Passage with which this trail connects in Cumberland. Interesting remnants of the canal are near the path. One section contained a series of beaver dams that kept water in the canal prism and the water was coated with green from floating algae and aquatic plants. In this verdant year everything was green including the water. There are several interesting, preserved locks along the way. Some 1800's (?) buildings near locks are also preserved. This is worth visiting for the history and the workout on foot or bike using the old towpath. Sad that the Paw Paw Tunnel work interrupts the biking flow. See more..
4.5 Sideling Hill Overlook & Rest Area (99 reviews)
- Breathtaking Views!
Points of Interest & Landmarks

I travel to Deep Creek (McHenry, MD) at least twice a year and I love stopping here for a pit stop to use the restroom, take a break, and take in the beautiful views. The highway is sliced directly through a large mountain and the views on both sides are gorgeous. See more..
4.5 Cumberland Visitor Center (71 reviews)
- National Park
Sunday: 9:00 AM - 5:00 PM Visitor Centers

We were surprised that this is part of the National Park system. My grandchildren aged 11 and 9 were able to earn their badges. Museum is full of interesting information about the C & O Canal. We were able to walk along the tow path and see an actual barge. The Park Ranger was so very nice to the boys. They were a little disappointed that the gift shop was closed. See more..
4.5 Allegany Museum (58 reviews)
- Worth a stop and convenient location - downtown Cumberland
Sunday: 1:00 PM - 4:00 PM Speciality Museums

Nice little museum with lots of history. We loved the first floor. My kids who are 2 and 4 were able to touch some things and press buttons, and we spent about an hour there. I loved learning about the evolution of cars and road conditions. The second floor was a Smithsonian exhibit but, surprisingly, much less interesting and the kids couldn’t touch most things. So I would recommend going if your kids are older and know how to read. The two wife and husband volunteers were very welcoming and friendly. Both did a great job engaging with our girls. See more..
4.5 Charis Winery & Distillery (36 reviews)
- Always a great experience!
Sunday: 2:00 PM - 6:00 PM Distilleries • Wineries & Vineyards

Local winery and distillery in downtown Cumberland at the Canal Place Shops. Wine and spirits produced on premises. Dry premier whites and reds as well semi-sweet to sweet fruit blends. We try to have a wine for everyone's pilot! We also produce Pomace Brandy- as well moonshine, rum and bourbon. Charis also has Savage Soaps available for purchase. Coming soon will be the introduction of Extra Virgin Olive Oils and Balsamic Vinegars! See more..
4.5 Emmanuel Episcopal Church (32 reviews)
- Beautiful Church, Great History
Sunday: 8:00 AM - 6:00 PM Religious Sites

Emmanuel Episcopal Church is on the original site of Fort Cumberland. It still has tunnels used in case of an attack. It also has beautiful grounds and Louis Comfort Tiffany windows. If you love history and historical buildings, you should make a stop. See more..
4.5 Gordon-Roberts House (26 reviews)
- Can't believe this is in Cumberland
Historic Sites

This house is huge, owned by an influential rail road baron family in Cumberland, which was the Queen City to Baltimore's King City. It is just huge for such a small town sitting on Washington Street with lots of other mansions. An excellent tour. An undiscovered gem. They start off the tour with hot tea and cookies. You will learn about Cumberland through the history of the house. Well worth it.... See more..
4.5 1812 Brewery (14 reviews)
- Worth a trip
Sunday: 1:00 PM - 8:00 PM Spent 1-2 hours Breweries

This was totally worth the drive. We are about 2.5 hours away. This place has lots of history, great, friendly service, great indoor and outdoor space and great beer. On Friday afternoon they had a food truck and live music as well. Loved the Stout but the Vienna Lager and others were also really good. We spent several hours there, reading the history, looking at the artifact wall and talking to the staff to learn more about it. See more..
4.5 Allegany Fairgrounds (9 reviews)
- Stunning
Spent More than 3 hours Points of Interest & Landmarks

Stunning landscape in all directions - a great location for the annual Delfest. The view was as good as the music. Can't wait to return. See more..
4.5 Fort Cumberland Emporium (9 reviews)
- Great place for those who love antique shopping.
Sunday: 11:00 AM - 4:00 PM Spent 1-2 hours Antique Shops

Great shop for anyone who loves antiques and collectibles. A definite place to visit in Downtown Cumberland. The shop has three floors and is filled so you need to make sure you allot some time to see it all. See more..
4.5 Allegany County Courthouse (3 reviews)
- Nice historic landmark in town
Spent < 1 hour Points of Interest & Landmarks • Government Buildings

The Allegany County Courthouse was built in 1893 with a Richardsonian style (based on history of the building). It is situated on top of the hill on the historic Washington Street above the Wills Creek. Visitors can see from all sides when approaching Cumberland. The handsome read brick building with tall tower dominate the skyline of the city along with a few church spires. If you have a chance, walk up the hill (about 15 minutes from the C&O canal park to see the detail of the building and the original site of the Washington's Headquarter at the corner of the building. See more..
4.5 C. William Gilchrist Museum of the Arts (3 reviews)
- Allegany Watercolor Artists
Art Museums
Nice open area, beautiful exhibit of artist works inspired us to look at more art galleries in the area. Reasonable prices for art on sale. See more..
4.0 George Washington's Headquarters (43 reviews)
- Historical Interest
Historic Sites

We found this during our morning walk around Cumberland. There is an audio that you can play anytime which explains about the cabin and how it was used during history. It was extremely interesting. It is part of a historical walk through Cumberland. See more..
4.0 History House (3 reviews)
- Western Maryland Must See
Historic Sites

Tour of a historic mansion built in 1867. See more..
4.0 Constitution Park (1 review)
- City Park, with lots to do
Sunday: 12:00 AM - 7:00 PM Spent 2-3 hours Parks • Playgrounds
A nice City-maintained facility, with a large pool (admission fee) and many hiking trails. it has a ball field, and the panoramic view of the city from behind the ball field is great. playgrounds for the younger set. Pavilions. See more..
3.5 Bell Tower Building (2 reviews)
- A unique, historical building
Architectural Buildings

Built in the 1880's for the city Police Department and jail, the building is still in use by the Chamber of Commerce. They'' be happy to let you look around inside. City Hall is in front of the building, and to the left (facing the bell tower) the building was a court house, post office, and police headquarters. Behind the building, a short walk across Mechanic street bring you to a old Fire Company building, and a natural spring, once used to feed a mill race for "Mechanic" Street. It is now drained underground into Will's Creek. See more..
Cornerstone Baptist Church (0 review)
Churches & Cathedrals
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Embassy Theatre (0 review)
Sunday: 1:00 PM - 5:30 PM Spent 1-2 hours Theaters

The Embassy Theatre provides live performance, theatre and music for both visitors and local patrons. Built in 1931 in the Art Deco style, the Embassy spent its first couple decades as a cinema before being converted to retail usage. In 1999, Broadway actor Mark Baker began the renovation of the Embassy into its current use as a live performance space. See more..