When most people picture a Maryland getaway, they probably think of the Chesapeake Bay or the beaches along the Eastern Shore. Allegany County, the mountain side of Maryland, couldn’t feel more different. Tucked into the westernmost part of the state, this mountain region is defined by historic downtowns, scenic railways, winding bike trails, and enough locally owned coffee shops and restaurants to fill an entire weekend.
We recently spent several days exploring Cumberland, Frostburg, and the surrounding area, and what stood out most wasn’t one singular stop. It was how easy it was to relax. One morning we were walking down Baltimore Street with a coffee later that afternoon we were pedaling a rail bike through the mountains; and the next day we were paddling Rocky Gap Lake.
If you’re looking for a weekend trip that’s equal parts outdoor adventure and small-town charm, Allegany County should be on your radar.
Where Is Allegany County, Maryland?
Allegany County sits in the northwest corner of Maryland, where it connects Pennsylvania and West Virginia. It’s about a two-hour drive from Pittsburgh, and just a bit shorter from Morgantown, West Virginia.
If you’re visiting, you’ll likely spend most of your time in Cumberland, the county seat and historic heart of the region. Don’t overlook nearby Frostburg, though. Just a 15-minute drive away, the two towns complement each other well and are easy to explore in the same trip.
As New Yorkers, we’re big on public transit, but for this trip, renting a car was so important. Downtown Cumberland is walkable, but for most other experiences you’ll need a car. Thats probably a no-brainer for many people, but its so different from our norm I wanted to mention it.
What Makes Allegany County Worth Visiting?
The first thing we noticed about Allegany County was just how charming Cumberland is. When you walk down Baltimore Street, you’ll find beautifully preserved historic buildings that reflect the city’s past as an important transportation hub.
It’s not just about the history. A two-year revitalization project helped transform Baltimore Street with wider walking paths and green spaces. It turned it into a proper place to comfortably wander and explore local businesses. The project was completed in 2024, and i already can’t help but wonder how many locally owned businesses will have storefronts there in the coming years.
When you get out of town, you’ll quickly understand why Allegany County is known as Mountain Maryland. Hiking trails, the Great Allegheny Passage, scenic overlooks, and winding mountain roads are all within a short drive.
Where to Stay in Cumberland, MD
The simple answer to this question is The Wills Hotel. The location is ideal, right in the heart of historic Baltimore Street. You’re within easy walking distance of great restaurants, coffee shops, the C&O Canal Towpath, and the Western Maryland Scenic Railroad.
Located inside a beautifully restored historic building, The Wills Hotel finds the perfect balance of new and old. The architecture reflects Cumberland’s history, and the rooms feel modern, spacious, and designed with intention. Our room had large windows that filled the room with natural light, plenty of space to unpack and hang our clothes, and a coffee station, which is always important.
The hotel also has several details that make settling in a little easier. In the lobby, there is a small market that includes snacks and drinks like locally made lemonade and toiletry odds and ends. You know the ones, like toothpaste that easily end up forgotten.
They also have a beautiful bar and restaurant, 1867-A Modern Chophouse, that connects directly to the lobby. After a day of outdoor adventures its so nice to get showered and only need to go down the elevator for a great meal.
Where to Eat in Allegany County
One of the best surprises of our trip was how much good food we found. We expected great hiking trails, but we didn’t expect to leave talking about latte flights. In fact, we enjoyed the restaurants, coffee shops, and ice cream shops so much that we ended up writing an entire guide dedicated to where to eat in Allegany County.
If you’re only in town for a weekend, I’d start your mornings at Cafe Mark for breakfast and one of its incredibly fun latte flights. Basecamp Coffee or Clatter Cafe in Frostburg for that mid afternoon pick me up. For lunch, Baltimore Street Grill is the go-to; crabcakes are a must. I opted for the crabcake sandwich, and it had so much crab. 1867 – A Modern Chophouse inside The Wills Hotel is an easy choice for a lovely meal fit for a weekend away. Before heading back to your hotel, pick one of the ice cream spots off the Ice Cream Trail, our favorite was Queen City Creamery.
The Best Things to Do in Allegany County
Explore Historic Downtown Cumberland
The best way to experience downtown Cumberland is simply to wander. Baltimore Street is lined with beautifully preserved historic buildings, locally owned shops, and cafes. Give yourself time to just wander and pop into anything that sparks your curiosity. Make sure to turn off Baltimore Street their are some cool boutique shops off the main drag.
Spend an Afternoon in Frostburg
Located 15 minutes from Cumberland, Frostburg is home to Frostburg State University. The town has its own set of cafes, and shops waiting to be explored.
Our favorite stops were Clatter Café and Main Street Books. The rainbow sticker in the window of Main Street Books immediately made us both smile, and inside we found books by queer authors, cards for LGBTQ weddings, and exactly the vibes we love from an independent, locally owned bookstore.
Experience Allegany County by Rail
Railroads are a part of Allegany County’s history, and there are still multiple ways to experience them.
One option is to ride the Western Maryland Scenic Railroad through the mountains aboard beautifully restored rail cars. It’s a short ride, and they have bathrooms and snacks. Another option, and the one we chose, is booking a tour through Tracks & Yaks. They have a bunch of tour options with various lengths on railbikes. The ride was easy, much of it downhill coasting rostburg to Cumberland through tunnels, over bridges, and past beautiful mountain scenery ended up being one of our favorite experiences of the entire trip.
EveryQueer Tip: Here is a video of our whole railbike experience. We booked the Queen City Combo from Frostburg to Cumberland. We opted to take the train back, but they also have a kayak back option that tons of people in our group did.
Get Outside on the Great Allegheny Passage
The Great Allegheny Passage is a rail trail that stretches 150 miles between Cumberland and Pittsburgh. It’s a really beautiful place for a multi-day cycling adventure or just a short ride. The trail has rolling hills and many viewpoints with big payoffs. There are also plenty of little towns to stop in along the way to fill water bottles or grab a meal.
Visit Rocky Gap State Park
If you only have time for one outdoor adventure, Rocky Gap State Park might be my choice. We rented a cutie little paddle pontoon from Wheelzup, grabbed a couple snacks and drinks, and spent as much time floating as we did paddling. We had no idea what to expect, but the water was calm, the weather was perfect we could have stayed out there for hours.
The lake also has designated swimming areas and grills to be used. There were tons of families out picnicking it was adorable. If you’d rather stay inside, Rocky Gap Casino Resort has great lake views from the casino and restaurant.
Follow One of Allegany County’s Food Trails
I love to eat so one of the most fun ways to explore Allegany County was by following the self-guided food trails. The hardest part is honestly choosing which one there is a Coffee & Donut Trail, Ice Cream Trail, or the Mountain Maryland Orange Crush Trail. Even if you dont finish any one trail, it’s a fun excuse to bop around and visit some spots you would have otherwise missed. There are even places that proudly sit on both the Coffee & Donut Trail and the Ice Cream Trail; talk about an elite combo! We’re looking at you, Mountain City Coffee House & Creamery.
Visit the Allegany County Fair (Summer Only)
If your visit happens to line up with the Allegany County Fair, don’t skip it. We spotted a sign for it on our first night in town and immediately knew we wanted to go. It ended up being one of the most nostalgic stops of the trip. The fair had all the classics, from a Ferris wheel and swing rides to live entertainment and carnival games. Of course, the food was a highlight too, with every fried treat imaginable, from broccoli to Oreos. Admission was just $1 on the first Friday when we visited.
What stayed with us most was how many lesbian couples we saw. Multiple LGBTQ+ couples were holding hands, playing games together, and openly showing affection. It was sweet to see, but it also felt important. Seeing so many queer couples comfortably being themselves at a classic small-town county fair offers a peek into the community. Allegany County might not have a lesbian bar, but it is a place where you can kiss your girlfriend at a carnival without thinking twice. That mattered to us, and made it the perfect last stop on our way out of town.
