20 Things to Do in Cumberland, Maryland (MD)

Cumberland, Maryland, is a charming city with a rich historical legacy and scenic beauty, nestled in the heart of Allegany County. Often referred to as the "Gateway to the West," it played a crucial role during America's expansion and development. Located near the Allegheny Mountains, Cumberland offers a wealth of experiences, blending its fascinating past with modern attractions, just like the things to do in Havre de Grace, Maryland.

From exploring its historical sites to enjoying outdoor adventures, this city has something for everyone. In this blog post, we'll take a deeper dive into the best things to do in Cumberland, Maryland, while also helping you decide when to visit and how to plan your perfect trip.

Unique Facts About Cumberland

Historic Significance

Cumberland’s historical importance stretches far beyond its picturesque landscapes. In the 19th century, it became a pivotal transportation hub, connecting the Chesapeake and Ohio Canal with the Baltimore and Ohio Railroad. This connection not only contributed to the city’s economic boom but also played a significant role in the westward expansion of the United States. If you’re nearby, consider exploring the various things to do in Hagerstown, Maryland (MD), which also offers a rich historical backdrop and scenic views. Today, the historical significance of Cumberland can still be felt through its well-preserved landmarks and museums.

Cultural Heritage

Cumberland’s arts scene is vibrant and thriving. The Allegany Arts Council serves as a cornerstone for local culture, offering exhibits, performances, and events that showcase the best of the region's artistic talents. Additionally, the Cumberland Theatre presents a variety of productions throughout the year, giving visitors a taste of local creativity and theatrical history. Whether you’re an art lover or simply enjoy experiencing local culture, Cumberland is sure to impress.

Architectural Highlights

Cumberland’s Downtown Historic District is a treasure trove of architectural gems. The area features late 19th and early 20th-century buildings, such as former banks, hotels, and department stores. These structures not only highlight the city’s growth during its industrial era but also provide a unique glimpse into the architectural styles of the time. For history enthusiasts and architecture aficionados, a walk through Cumberland’s downtown is a must, and similarly, there are plenty of things to do in St. Michaels, Maryland (MD) that offer a blend of rich history and charm.

20 Things to Do in Cumberland, Maryland (MD)

Cumberland, Maryland, is a charming city nestled in the western part of the state, rich in history, culture, and natural beauty. From scenic train rides to peaceful parks and historic sites, Cumberland offers something for everyone. Whether you’re an outdoor enthusiast or a history buff, the city has plenty to explore. Here’s a guide to some of the best things to do in Cumberland.

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1. Great Allegheny Passage

Short Description of Activity
The Great Allegheny Passage (GAP) is a renowned 150-mile trail stretching from Cumberland, Maryland, to Pittsburgh, Pennsylvania. It’s a perfect destination for cyclists, hikers, and nature lovers. This trail takes you through scenic landscapes, tunnels, and bridges, offering a truly immersive outdoor experience.

Pros and Cons
Pros:

• Breathtaking views of the Appalachian Mountains.

• Ideal for outdoor activities like biking and hiking.

• Easy access from downtown Cumberland.

Cons:

• Some sections of the trail can be challenging for beginners.

• Requires good weather for a pleasant experience.

Key Attractions and Events:

• Annual cycling events and festivals.

• Historic sites along the trail, including tunnels and old rail bridges.

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2. C&O Canal

Short Description of Activity
The Chesapeake & Ohio Canal (C&O Canal) runs alongside the Potomac River, offering a mix of history and nature. It’s perfect for hiking, biking, and even boat rides, providing a scenic path through forests, wildlife areas, and historic lock houses.

Pros and Cons
Pros:

• A peaceful, scenic environment perfect for outdoor enthusiasts.

• Rich in history with numerous historical landmarks along the canal.

Cons:

• Some areas may be flooded or closed during heavy rains.

• Parts of the trail may be rugged for those with limited mobility.

Key Attractions and Events:

• Historic lock houses.

• Annual C&O Canal Days festival celebrating the canal's history.

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3. Western Maryland Scenic Railroad

Short Description of Activity
The Western Maryland Scenic Railroad offers a step back in time as it operates historic trains through the mountains and valleys of Western Maryland. Enjoy a leisurely ride with views of the surrounding landscapes, including scenic rivers and rugged terrain.

Pros and Cons
Pros:

• Unique way to see the local area, offering spectacular mountain views.

• Family-friendly and educational experience.

Cons:

• Train rides can be pricey for families.

• Limited schedules during certain seasons.

Key Attractions and Events:

• The Polar Express during the winter season.

• Regular excursions throughout the year.

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4. Rocky Gap State Park

Short Description of Activity
Rocky Gap State Park offers over 3,000 acres of outdoor fun, with opportunities for hiking, fishing, boating, and camping. With its beautiful lake, forests, and mountain views, it's a great destination for outdoor recreation.

Pros and Cons
Pros:

• Variety of outdoor activities like fishing, hiking, and picnicking.

• Beautiful setting, perfect for a family outing or weekend retreat.

Cons:

• Can get crowded on weekends and during peak seasons.

• Limited services in the off-season.

Key Attractions and Events:

• Rocky Gap Lake for boating and fishing.

• Hiking trails with amazing views of the mountains.

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5. Cumberland Visitor Center

Short Description of Activity
The Cumberland Visitor Center is a great starting point for anyone visiting the city. Located in a historic railroad station, it offers maps, information on local attractions, and friendly advice from knowledgeable staff.

Pros and Cons
Pros:

• Excellent starting point for exploring Cumberland.

• Friendly staff offering local insights and recommendations.

Cons:

• Limited hours during the off-season.

• Basic exhibits without much interactivity.

Key Attractions and Events:

• Historic building that used to be a railroad station.

• Information on seasonal events and tours around Cumberland.

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6. Allegany Museum

Short Description of Activity
The Allegany Museum focuses on the history of Cumberland and Allegany County. It’s an excellent place for history enthusiasts, with exhibits showcasing the area’s industrial past, railroad history, and cultural development.

Pros and Cons
Pros:

• Rich historical exhibits focusing on the region.

• Free admission makes it accessible for families.

Cons:

• Relatively small in size compared to other museums.

• Some exhibits might not appeal to all visitors.

Key Attractions and Events:

• Regular exhibits focusing on local history.

• Special events and educational programs for children.

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7. George Washington's Headquarters

Short Description of Activity
George Washington’s Headquarters in Cumberland is where the first president of the United States stayed during his military service. The headquarters has been preserved as a historical site, offering insights into Washington’s early military career.

Pros and Cons
Pros:

• Deep historical significance, especially for history enthusiasts.

• Educational and interactive tours available.

Cons:

• Small building with limited interior to explore.

• Somewhat difficult to access for visitors with mobility issues.

Key Attractions and Events:

• Historical reenactments during certain times of the year.

• Guided tours explaining George Washington’s time in Cumberland.

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8. Emmanuel Episcopal Church

Short Description of Activity
Emmanuel Episcopal Church is one of Cumberland's oldest churches, known for its beautiful stained glass windows and impressive architecture. It offers a serene setting for reflection and is a great spot for photography.

Pros and Cons
Pros:

• Beautiful, historic architecture and stained-glass windows.

• Peaceful, reflective environment.

Cons:

• Not many interactive experiences for visitors.

• Limited hours of operation.

Key Attractions and Events:

• Beautiful stained glass windows.

• Historic church tours.

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9. Canal Place

Short Description of Activity
Canal Place is an area where history and recreation come together. It includes a park, trails, and a visitor center with great views of the C&O Canal. It’s also a hub for local shops, restaurants, and outdoor activities.

Pros and Cons
Pros:

• Great spot to relax and enjoy local shops and restaurants.

• Beautiful outdoor park space.

Cons:

• Can get crowded during peak tourist seasons.

• Limited activities in winter months.

Key Attractions and Events:

• Events like outdoor concerts and festivals.

• The scenic views of the canal.

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10. Washington Street Historic District

Short Description of Activity
The Washington Street Historic District is a collection of well-preserved buildings dating back to the 19th century. It’s the perfect place for a leisurely walk, offering a glimpse into Cumberland’s past with beautiful architecture and landmarks.

Pros and Cons
Pros:

• Great for history buffs and architecture lovers.

• Offers a peaceful stroll through a historic area.

Cons:

• Some buildings may be closed to the public.

• Limited activities aside from sightseeing.

Key Attractions and Events:

• Historic homes and buildings showcasing Cumberland’s past.

• Walking tours that bring the area’s history to life.

11. Sideling Hill Overlook & Rest Area

Short Description of Activity
Sideling Hill Overlook is a scenic spot located along Interstate 68. This spot offers breathtaking views of the Appalachian Mountains and the surrounding valleys. It’s a great place to stop, stretch your legs, and take in the natural beauty of the area.

Pros and Cons

• Pros:

  • Stunning panoramic views of the Appalachian Mountains.

  • Peaceful and relaxing atmosphere.

  • Convenient rest area for travelers.

• Cons:

  • Limited amenities at the site.

  • Can be crowded during peak travel seasons.

Key Attractions and Events

• Observation platform with incredible views.

• Excellent location for photography.

• Part of a larger series of scenic overlooks in the region.

12. Thrasher Carriage Museum

Short Description of Activity
The Thrasher Carriage Museum showcases a remarkable collection of carriages and horse-drawn vehicles. It’s a fantastic place to learn about the history of transportation before the advent of the automobile.

Pros and Cons

• Pros:

  • Impressive collection of historical carriages.

  • Well-organized exhibits providing a glimpse into 19th-century life.

  • Educational and engaging for all ages.

• Cons:

  • The museum might be too specific for visitors uninterested in history.

  • Small in size, so a visit can be brief.

Key Attractions and Events

• Historic horse-drawn vehicle displays.

• Artifacts and memorabilia from the 19th century.

• Occasional special events showcasing local culture and history.

13. Cumberland Narrows

Short Description of Activity
The Cumberland Narrows is a scenic and historic area known for its impressive natural landscape. The narrow passage through the mountains offers a fascinating combination of natural beauty and historical significance.

Pros and Cons

• Pros:

  • Ideal for outdoor enthusiasts and photographers.

  • Rich historical context and significance.

  • Peaceful and serene setting.

• Cons:

  • Not much infrastructure or facilities nearby.

  • Limited accessibility for those with mobility issues.

Key Attractions and Events

• Hiking trails with incredible mountain views.

• Rich history related to early American exploration.

• Great spot for bird watching and nature walks.

14. Constitution Park

Short Description of Activity
Constitution Park is a lovely green space in Cumberland, perfect for outdoor recreation. It features walking paths, picnic areas, and a pond, making it a great spot for a relaxing day out.

Pros and Cons

• Pros:

  • Family-friendly with plenty of activities for kids.

  • Beautiful green space with picnic areas.

  • Peaceful and well-maintained.

• Cons:

  • Limited parking during peak times.

  • The park can be quiet and a little underwhelming for those looking for more excitement.

Key Attractions and Events

• Seasonal outdoor concerts and festivals.

• Fishing and picnicking areas.

• Scenic walking trails around the pond.

15. LaVale Toll Gate House

Short Description of Activity
The LaVale Toll Gate House is a historical site that once served as a tollhouse during the 19th century. Visitors can explore its architecture and learn about the history of the National Pike and transportation in the early days of the U.S.

Pros and Cons

• Pros:

  • Rich in history and an excellent stop for history enthusiasts.

  • Well-preserved building with informative signage.

  • Provides insight into early American travel.

• Cons:

  • Limited hours of operation.

  • Small in scale, so a quick visit.

Key Attractions and Events

• Historical displays about the National Pike.

• Educational tours about early U.S. travel and toll systems.

• Period-specific exhibits showcasing toll house life.

16. Gordon-Roberts House

Short Description of Activity
The Gordon-Roberts House is a beautiful Victorian-era home in Cumberland, now serving as a museum. The house is an excellent example of 19th-century architecture and offers a glimpse into the lives of the prominent families who lived there.

Pros and Cons

• Pros:

  • Well-preserved Victorian architecture.

  • Fascinating tours that highlight local history.

  • Knowledgeable guides provide in-depth information.

• Cons:

  • Limited hours, especially off-season.

  • Not as interactive as some other historical sites.

Key Attractions and Events

• Period furniture and decorations.

• Special events showcasing local history.

• Guided tours that delve into the house’s history.

17. Cumberland Bone Cave

Short Description of Activity
Cumberland Bone Cave is a unique natural attraction where visitors can explore the site of ancient discoveries. The cave contains fossils and remnants of prehistoric creatures that once roamed the area.

Pros and Cons

• Pros:

  • A fascinating site for archaeology and paleontology enthusiasts.

  • Educational and informative tours.

  • Unique opportunity to see fossils in their natural setting.

• Cons:

  • Not suitable for visitors with mobility issues.

  • Limited visitor facilities.

Key Attractions and Events

• Fossils and bones from ancient animals.

• Tours explaining the geological and historical significance.

• Great spot for geology and history enthusiasts.

18. Downtown Cumberland Historic Walking Tour

Short Description of Activity
The Downtown Cumberland Historic Walking Tour offers visitors a chance to explore the city's rich history through its well-preserved architecture. The tour highlights important landmarks, historical sites, and offers a glimpse into Cumberland’s past.

Pros and Cons

• Pros:

  • Great for history lovers and architecture enthusiasts.

  • Walking tour makes it easy to see a lot in a short time.

  • Learn about the local history and culture.

• Cons:

  • Can be tiring for those not used to walking.

  • The weather can be a factor, especially during the summer.

Key Attractions and Events

• Historic buildings and landmarks.

• Guided tours that provide deep insights into Cumberland’s past.

• Occasional historical reenactments and cultural events.

19. Embassy Theatre

Short Description of Activity
The Embassy Theatre in Cumberland is a historic venue offering a wide range of live performances, from plays and musicals to concerts and special events. It’s a great place to enjoy local culture and entertainment.

Pros and Cons

• Pros:

  • Beautiful historic venue with excellent acoustics.

  • Diverse programming that appeals to various audiences.

  • Charming, intimate setting for performances.

• Cons:

  • Limited seating capacity.

  • Shows may be limited depending on the time of visit.

Key Attractions and Events

• Live performances throughout the year.

• Special events and concerts showcasing local talent.

• Historic interior that adds to the charm of the experience.

20. Charis Winery & Distillery

Short Description of Activity
Charis Winery & Distillery offers an authentic experience for wine and spirits enthusiasts. With a beautiful vineyard and distillery, visitors can sample locally made wines and spirits while enjoying the peaceful countryside.

Pros and Cons

• Pros:

  • Great for wine and spirit lovers.

  • Relaxing atmosphere with scenic views.

  • Friendly and knowledgeable staff for tastings.

• Cons:

  • Limited food offerings on-site.

  • May not be suitable for families with young children.

Key Attractions and Events

• Wine and spirit tastings.

• Vineyard tours to learn about the production process.

• Special events and festivals throughout the year.

Best Time to Visit Cumberland

Cumberland, Maryland, experiences four distinct seasons, each offering unique opportunities for visitors. Here’s a breakdown of the best times to visit depending on the activities you prefer.

• Spring (March to May): As the weather warms up, Cumberland comes alive with blooming flowers and mild temperatures. It’s the perfect time for outdoor activities like hiking along the Great Allegheny Passage and biking through the city’s scenic landscapes.

• Summer (June to August): The summer months bring warm weather, making it an ideal time to visit Rocky Gap State Park for activities like boating, swimming, and fishing. In addition, the city hosts several festivals and events, offering a lively atmosphere.

• Fall (September to November): With cooler temperatures and vibrant autumn colors, fall is one of the best times to explore Cumberland’s natural beauty. Scenic drives, hikes, and visits to the historic sites are all enhanced by the colorful foliage.

• Winter (December to February): If you're a fan of winter sports, Cumberland is the place to be in winter. The snowfall creates perfect conditions for skiing, snowboarding, and snowshoeing. The festive season also brings special events that add to the city’s charm.

Unique Gems of Cumberland

Cumberland is home to several unique gems that offer historical, cultural, and natural attractions. Here are a few must-visit sites when in town:

Canal Place Heritage Area

The Canal Place Heritage Area is one of Cumberland’s most iconic landmarks. It’s the western terminus of the Chesapeake and Ohio Canal and offers visitors a chance to step back in time. You can explore a replica canal boat, enjoy a picnic in the scenic area, or visit the Cumberland Visitor Center, which features interactive exhibits about the region’s history.

George Washington's Headquarters

This small cabin in Cumberland is where George Washington stayed during his time as a young aide to General Braddock. The one-room cabin provides a fascinating insight into early American history and the young commander’s experiences before he became the first President of the United States. If you're exploring nearby, consider adding things to do in Annapolis, Maryland (MD) to your itinerary for a deeper dive into the region’s rich past.

Sideling Hill Overlook & Rest Area

For breathtaking views, head to Sideling Hill Overlook. Located just outside Cumberland, this spot offers panoramic views of the Allegheny Mountains and allows visitors to observe impressive geological formations. It’s a perfect stop for nature lovers and photographers looking to capture Cumberland’s stunning landscapes.

Suggested Day Itinerary

Here’s a suggested day itinerary for those looking to explore the best of Cumberland in one day:

Morning

Begin your day with a guided tour of the Allegany Museum, where you’ll learn about the region’s rich history, including its role in transportation and industry.

Late Morning

Hop aboard the Western Maryland Scenic Railroad for a picturesque journey to Frostburg. This 16-mile ride takes you through the Allegheny Mountains, providing a glimpse of Cumberland’s scenic beauty.

Afternoon

Once you reach Frostburg, enjoy lunch at a charming local café, then head over to the Thrasher Carriage Museum. This museum houses an extensive collection of horse-drawn vehicles, offering a glimpse into the past when transportation relied on horse power.

Evening

Return to Cumberland in the evening and enjoy dinner at one of the downtown restaurants. Many local spots feature a cozy atmosphere and delicious meals inspired by the city’s history and culture.

How to Reach Cumberland, Maryland

Cumberland is easily accessible by various modes of transportation, making it a convenient destination for visitors.

By Car

Cumberland is located along Interstate 68, which connects travelers from both the east and west. It’s a smooth drive from nearby cities such as Baltimore, Washington, D.C., and Pittsburgh, making it an easy road trip.

By Train

The Western Maryland Scenic Railroad offers scenic excursions from Cumberland to Frostburg. This historic route provides a unique and enjoyable way to travel through the mountains.

By Air

The nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is approximately a two-hour drive from Cumberland. If you’re flying in from another city, BWI is the best option for reaching Cumberland.

Conclusion

Cumberland, Maryland, offers a delightful mix of history, culture, and natural beauty. Whether you’re exploring historical sites, enjoying outdoor activities, or experiencing the vibrant arts scene, there’s something for everyone in this charming city. With its convenient location and diverse offerings, Cumberland is the perfect destination for a weekend getaway or a longer stay.

If you’re looking to explore a city rich in heritage, stunning landscapes, and unique attractions, Cumberland is an excellent choice. Start planning your visit today and immerse yourself in the many wonders this historic Maryland city has to offer.

FAQs

What outdoor activities are available in Cumberland, Maryland?

Cumberland offers a variety of outdoor activities, including hiking and biking along the Great Allegheny Passage, boating and fishing at Rocky Gap State Park, and exploring the C&O Canal Towpath.

Are there family-friendly attractions in Cumberland?

Yes, Cumberland is home to several family-friendly attractions, including Constitution Park, which features playgrounds, picnic areas, and a public swimming pool. Additionally, the Western Maryland Scenic Railroad offers a historic train experience for families to enjoy.

What cultural events take place in Cumberland?

Cumberland hosts numerous events throughout the year, including the Heritage Days Festival, Friday After Five concerts, and the Farmer’s Market at Canal Place.