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From scenic rail rides and mountain trails to breweries, colleges, major employers, and indoor arenas, you’re surrounded by experiences minutes from The Wills Hotel. Explore heritage sites, outdoor escapes, shopping and dining downtown, corporate campuses, and sports venues. Then return to modern comfort. Below, you’ll find can’t-miss picks to plan your stay and discover more of Mountain Maryland.
70,000 acres of majestic nature, internationally recognized bike trails, three centuries of American history, a diverse food, brewery, and winery scene, and an endless amount of outdoor adventure. The Trail Starts Here!
Ride vintage rail from Cumberland to Frostburg through the Allegheny Mountains, passing Helmstetter’s Curve and the Brush Tunnel. Seasonal excursions include dinner trains, murder mysteries, and holiday events, with steam locomotive No. 1309 starring on select dates. It’s a photogenic, family-friendly activity.
Pedal or stroll the 150mile GAP rail trail linking Cumberland to Pittsburgh and connecting with the C&O Canal Towpath for a 335mile route to Washington, D.C. Expect lightly graded terrain, trail towns every 10 miles or so, and big views at the Eastern Continental Divide. Start at Mile 0 in Canal Place near downtown Cumberland.
Explore 184.5 miles of towpath along the Potomac River, ending in Cumberland. Hike, cycle, birdwatch, and visit historic lockhouses and aqueducts. Multiple visitor centers and trailheads make day trips easy. Download trip-planning tools or join ranger-led programs to add context to your canal adventure.
Cumberland's downtown Main Street District is a charming blend of historic character and vibrant local culture. With beautifully preserved architecture, unique shops, cozy cafés, a growing arts scene, and scenic mountain views, it offers visitors an inviting place to explore and unwind.
Home to the Allegany County Fair & Ag Expo and year-round events, the fairgrounds feature large indoor/outdoor venues and a half-mile dirt track. Look for concerts, festivals, and winter light displays. Check the calendar when planning your stay.
Just east of Cumberland, 3,000+ acres surround Lake Habeeb—famous for clear, blue water. Hike the Lakeside Loop, paddle, swim at sandy beaches, or visit the nature center. Scenic overlooks and hemlock forests offer year-round beauty minutes from town.
Play 600+ slots and table games, dine at multiple restaurants, and tee up at Maryland’s only Jack Nicklaus Signature Golf Course, all inside Rocky Gap State Park. Guests enjoy a spa, events, and lake views—easy to pair with a day on the trails.
Sip awardwinning craft beers at Western Maryland’s farm brewery, set in a repurposed 1812 barn on a scenic property. Expect live music, food trucks, and family friendly vibes. This is your relaxed stop after riding the GAP or exploring Downtown. Check the events page before you go.
Coast downhill from Frostburg on tandem or quad railbikes along the Western Maryland Railway line, gliding through the Brush Tunnel and past mountain views. Guided tours include shuttle return and combo packages with kayaking or the Scenic Railroad.
A Main Street accredited college town with indie shops, bakeries, taverns, galleries, and the historic Palace Theatre. It’s the western stop for the Scenic Railroad and launch point for rail biking. Plan a meal, grab a coffee, and explore local arts and history.
This 481-acre park offers an Olympic size pool (seasonal), a stocked fishing pond, four, large group picnic pavilions, a playground, and new hiking loops. Nearby Dan’s Rock Overlook serves dramatic valley views. A lowkey day park that’s perfect for families.
Maryland’s largest contiguous public forest (≈49,000 acres) offers primitive camping by permit, extensive hiking and biking trails, scenic overlooks, hunting (permit), and a self guided 44mile driving tour. It’s a serene, rugged escape within easy reach.
Comprehensive inpatient (CAR accredited) and outpatient rehab services—physical, occupational, and speech therapy—are available minutes from downtown. Whether you’re visiting or here on business, the hospital is a regional hub for specialty care.
Headquartered in Downtown Cumberland, Care Ventures provides rehabilitation management and related healthcare services to providers across the continuum. It’s part of the community’s healthcare ecosystem supporting residents and employers.
A major cabinetry manufacturer with a long presence in Cumberland, American Woodmark’s Allegany Plant underscores local industry and employment. The facility sits southwest of town in Barton Business Park.
Just a quick 5-minute drive from The Wills Hotel, Allegany College of Maryland offers a welcoming campus with athletics, cultural events, and community programs. Stop by for a Trojans sports game, art exhibit, or open lecture during your stay—immerse yourself in the local college experience and enjoy a taste of Cumberland’s vibrant scholarly spirit.
Head 15 minutes west on I‑68 to reach Frostburg State University, a scenic campus nestled in mountain views. Root for the Bobcats at football, soccer, or lacrosse games, or catch a cultural event like performances and exhibits. Take in the collegiate atmosphere and enjoy a day exploring the academic energy just beyond Cumberland.
The official city site offers event calendars, parking info, permits, and services helpful for planning your visit, attending downtown happenings, or exploring parks and recreation facilities like Gene Mason Sports Complex.
Stay current on local news, sports, and community events with the region’s newspaper—great for checking weekend happenings, feature stories, and weather before you head out.
Nearby Rocket Center, WV and Elkton, MD facilities contribute to advanced defense manufacturing and hypersonics and are key employers in the broader region. Their operations reflect the area’s engineering heritage and innovation.
IBM maintains federal consulting roles and technology operations in Rocket Center, WV. For business travelers, the site underscores the region’s federal and IT presence within a short drive of Cumberland.
This 55-acre riverfront complex offers soccer fields, ball diamonds, volleyball courts, tennis, BMX, and access to the C&O Canal. It’s ideal for pickup games or spectating local league play. Check facility details and field availability online. Temporarily closed due to recent flooding.
Catch Trojans basketball or volleyball in a renovated arena seating about 950, or attend special events. Named for the legendary NJCAA coach, it’s a lively venue close to downtown and an easy add to a sports-focused itinerary.
Visit the Parris N. Glendening Recreation Complex in Frostburg—about a 15-minute drive from your downtown stay. The 27-acre park boasts athletic fields, basketball courts, a playground, walking trails, and stocked fishing ponds. Bring the family, stretch your legs, or enjoy a lakeside snack after exploring Cumberland’s downtown scene.
Cheer on the Bobcats at Bobcat Stadium, a lively athletic venue featuring football, soccer, lacrosse, and track events. Just off I‑68, it’s around a 15-minute drive. Take in the college spirit and community excitement whether you’re here for a game or a special athletic event. A spirited way to connect with local life.
CTN Wedding Expo - 2026 Dates TBD
Hooley Pub Crawl - March 14, 2026
Come out for some fantastic live music in front of Mezzos, Friday, June 12th from 7:00PM - 10:00PM.
June 13th Noon-2:00PM.
Get out and explore all that our amazing area has to offer! Enjoy outdoor adventures, great restaurants, and train rides on the Western Scenic Railroad.
The music series brings together residents from various neighborhoods through the power of free, live music while generating foot traffic for local attractions and the historic city center. The Levitt AMP Cumberland Music Series showcases the scenic Festival Grounds at Canal Place with its water views and mountain scenery, and brings energy to a public space that has become a central gathering place for the arts and community.
Savor flavors from across the region at the Western Maryland Food Truck Festival on Saturday, June 13, 2026, from 12:00 PM to 8:00 PM at the Cresaptown Sports Complex, 12797 Darrows Lane, Cresaptown, MD. Enjoy a lineup of food trucks, craft beer and wine, live music, and family-friendly activities—all supporting local community programs.
The City of Cumberland is kicking off the week of America's 250th with a parade! Join us Saturday, June 27th at 1:00 pm to celebrate America's 250th Anniversary! The application for parade participants is now open! We are looking for floats, marching groups, dance groups, bands, car groups, organizations, animal units and more! Please fill out the form linked below before Monday, June 8th at 4:00 pm!
After the parade, hang around downtown until 6:00 pm for music, games, food trucks, drinks, restaurant specials, sales, and more! A detailed lineup of activities will come in the future!
Come out to Constitution Park for a great fireworks display! Show starts at 9:30PM. Learn how Allegany County is joining in on the commemoration of America's 250th anniversary here.
Night Traveler performs at Liberty Street Plaza from Noon-2:00PM.
Enjoy nine days of family fun at the Allegany County Fair & AG Expo, happening July 17–25, 2026, at the Allegany County Fairgrounds, 11490 Moss Avenue, Cumberland, MD. This beloved summer tradition features carnival rides, live music, agricultural exhibits, demolition derbies, and all your favorite fair foods. It’s the perfect way to celebrate community and country charm in the heart of Mountain Maryland.
Butterscotch Blonde performs at Liberty Street Plaza from Noon-2:00PM.
Enjoy a live musical performance from Taber Robinette, Saturday August 22nd from 12:00PM-2:00PM. Stop by Liberty Street Plaza for some unforgettable music from a local artist. Taber Robinette is a singer/songwriter from Cumberland, Maryland. He has been involved in music and theatre his entire life and is currently the frontman for the local rock band “Dry Spell”. When you catch Taber playing a solo show, you can expect to hear some of his original songs as well as alternative music from the 60s to today.
Stop by Liberty Street Plaza on Saturday, September 5th from Noon-2:00PM for some great live music from Folk 'em All Trio. Enjoy a variety of music from bluegrass to western swing, Jimmy Cliff to BB King. Enjoy shopping and good eats at a number of popular local eateries.
Stop by Hoffman Park on Sunday, September 6th for this family-friendly event. In its 8th year, the festival showcases Maryland's breweries, wineries, distilleries, and their products. Festival proceeds go to the Allegany County Animal Shelter. This family and dog-friendly event will feature live music, food & craft vendors, as well as kids activities. Festivities run from 12:00PM - 6:00PM.
Experience Cumberland’s rich history! The Heritage Days Weekend runs September 12–13, 2026, along Historic Washington Street in Downtown Cumberland, MD. Enjoy artisan markets, music, food, and living history displays—all in a charming historic setting.
Discover the spirit of Appalachia! The Appalachian Festival runs September 17–19, 2026, at Frostburg State University, 101 Braddock Road, Frostburg, MD, just a short drive from Cumberland. Enjoy authentic music, artisan crafts, regional cuisine, and family-friendly activities during this three-day celebration of mountain culture.
Paddle for a purpose! The YMCA Dragons by the Lake Festival takes place on Saturday, September 26, 2026, at Rocky Gap State Park, 12900 Lake Shore Drive, Flintstone, MD, just minutes from Cumberland. This exciting dragon boat racing event brings teams together for a day of fun, friendly competition, and community spirit—all supporting the YMCA of Cumberland.
Start the holiday season with sparkle! The Cumberland Tree Lighting will illuminate Historic Downtown on Friday, November 27, 2026, from 5:00 PM to 8:00 PM at Baltimore Street, Cumberland, MD. Enjoy festive lights, music, and the arrival of Santa—just steps from The Wills Hotel
Celebrate the season in downtown Cumberland! The Celebration of Lights & Holiday Market will take place on Saturday, November 28, 2026, from 2:00 PM to 8:00 PM at Canal Place Heritage Park, 13 Canal Street, Cumberland, MD. Enjoy dazzling lights, artisan vendors, live entertainment, and festive cheer.
Step into a winter wonderland! The beloved Storybook Holiday returns to Downtown Frostburg, MD, on Saturday, December 5, 2026, just minutes from Cumberland. Enjoy a full day of festive fun, including the Elf Olympics, holiday parade, carriage rides, crafts, and visits with Santa—all in a charming small-town setting that captures the magic of the season.
Cumberland’s WinterFest will light up Historic City Center on Saturday, December 12, 2026, from 4:00 PM to 9:00 PM. Enjoy artisan vendors, live music, carriage rides, cozy fire pits with s’mores, and festive holiday fun.
Ring in the New Year in style! Join the excitement at Cumberland’s New Year’s Eve Celebration on Thursday, December 31, 2026, from 10:00 PM to Midnight at Liberty Street Plaza, Baltimore & Liberty Streets, Downtown Cumberland, MD. Enjoy live music, giveaways, and the iconic ball drop at midnight
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