Cumberland

Day Trips

Make the most of your day with our curated plans, packed with Cumberland's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Begin your day with a hearty breakfast at a local café, savoring fresh-baked pastries and artisanal coffee. Afterward, stroll down the charming streets of the Historic District, where the architecture tells stories of centuries gone by. Don’t miss the opportunity to visit the Allegany Museum, where you can delve into the local history and culture.

afternoon
:

In the afternoon, grab lunch at a quaint bistro featuring farm-to-table dishes that showcase local flavors. After refueling, take a guided tour of the historic Gordon-Roberts House, an exquisite example of Victorian architecture filled with period furnishings. Spend some time wandering the nearby Canal Place Heritage Area, where you can enjoy the scenic views along the Chesapeake and Ohio Canal.

evening
:

As the sun sets, head to a local brewery for a taste of Maryland craft beer while enjoying live music. For dinner, indulge in a meal at one of Cumberland’s renowned restaurants, where you can try regional specialties like pit beef or crab cakes. Wrap up your evening with a leisurely walk along the canal, soaking in the tranquil ambiance under the stars.

day 2
Outdoor Adventures at Rocky Gap State Park
morning
:

Start your day with a refreshing hike at Rocky Gap State Park, where the trails wind through lush forests and offer breathtaking views of the lake. After your hike, enjoy a picnic breakfast by the water, surrounded by nature's beauty. Don’t forget to keep an eye out for local wildlife while you savor your meal.

afternoon
:

In the afternoon, rent a kayak or paddleboard to explore the serene waters of Lake Habeeb, where you can experience the calm and beauty of the park from a different perspective. Alternatively, take a leisurely bike ride along the scenic trails, breathing in the fresh air and enjoying the natural surroundings. After working up an appetite, grab lunch at the park's snack bar.

evening
:

As the evening approaches, relax at one of the park's scenic overlooks to catch a stunning sunset over the lake. For dinner, head back to Cumberland and try a cozy restaurant that serves hearty comfort food. End the night with a campfire at your accommodations, sharing stories and making s'mores under the stars.

day 3
Cumberland's Arts and Culture Scene
morning
:

Begin your day with a visit to the Arts & Entertainment District, where you can explore local galleries showcasing the work of Cumberland artists. Enjoy breakfast at a nearby café that features locally sourced ingredients to fuel your artistic adventure. Take your time browsing through the unique shops that offer handmade crafts and art pieces.

afternoon
:

After lunch, immerse yourself in the world of performing arts by attending a matinee show at the historic Palace Theatre. Once the curtains close, visit the nearby C&O Canal Interpretive Center to learn about the canal's history and its significance to the region. Explore the interactive exhibits and take a stroll along the canal towpath for some fresh air.

evening
:

As night falls, consider dining at a restaurant that specializes in international cuisine, giving your taste buds a world tour. After dinner, catch a live music performance at a local venue, where you can enjoy everything from folk to rock. Conclude your evening with a nightcap at a rooftop bar, enjoying stunning views of the city skyline.

day 4
Scenic Drive Along the Appalachian Mountains
morning
:

Kick off your day with a scenic drive along the winding roads of the Appalachian Mountains, taking in the breathtaking vistas and fall foliage if you're visiting in autumn. Stop at scenic overlooks to snap photos and breathe in the fresh mountain air. Consider packing a breakfast picnic to enjoy at one of the beautiful viewpoints.

afternoon
:

In the afternoon, visit the nearby town of Frostburg, where you can explore the Frostburg Museum and learn about the area's rich coal mining history. Afterward, take a leisurely hike on one of the nearby trails, allowing yourself to connect with nature and enjoy the sights and sounds of the forest. Stop for lunch at a local diner, where you can experience the warm hospitality of the mountain communities.

evening
:

Return to Cumberland for dinner at a restaurant that offers both local and comfort food favorites. After your meal, take a stroll through the city to admire the beautifully lit historic buildings. Wrap up your day by visiting a local coffee shop for dessert and a warm drink as you reflect on your adventures.

day 5
Family Fun at the Western Maryland Scenic Railroad
morning
:

Start your day with a family-friendly breakfast at a local pancake house, where everyone can enjoy a hearty meal. After breakfast, make your way to the Western Maryland Scenic Railroad for a nostalgic train ride through the picturesque countryside. The sound of the steam engine and the beautiful scenery will create lasting memories for everyone.

afternoon
:

After your scenic train ride, have lunch at a family-oriented restaurant before heading to the nearby city park for some outdoor fun. Spend the afternoon enjoying the park's playgrounds, picnic areas, and walking trails, allowing the kids to burn off some energy. Don’t forget to take a family photo in front of the park’s iconic landmarks.

evening
:

As evening approaches, consider dining at an interactive restaurant where kids can enjoy a meal while watching their food being prepared. After dinner, head back to your accommodations for an evening of board games or outdoor activities like stargazing. Enjoy some quality family time before winding down for the night.

day 6
Culinary Exploration of Local Flavors
morning
:

Begin your culinary journey with a visit to a local farmers market, where you can sample fresh produce and artisanal goods from local vendors. Enjoy a leisurely breakfast at a nearby café that uses farm-fresh ingredients in their dishes. Take your time to chat with the vendors and learn about their farming practices and products.

afternoon
:

In the afternoon, join a cooking class at a local culinary school, where you can learn to prepare traditional Maryland dishes under the guidance of a skilled chef. After cooking, enjoy the delicious meal you created together, along with some local wine or craft beer. Spend some time exploring the surrounding area, perhaps stopping at a local vineyard or distillery for a tasting.

evening
:

As evening falls, choose a restaurant that showcases a farm-to-table concept, allowing you to experience the freshest flavors of the region. Savor a multi-course meal that highlights seasonal ingredients and local specialties. Conclude your culinary adventure with a dessert made from local ingredients at a charming dessert shop.

day 7
Nature and Wildlife at the Great Allegheny Passage
morning
:

Start your day with a bike rental from a local shop to explore the Great Allegheny Passage, a scenic trail stretching from Cumberland to Pittsburgh. Pedal along the beautiful route, enjoying the lush greenery and occasional views of the river. Stop for a mid-morning snack at one of the trail’s rest areas, soaking up the peaceful surroundings.

afternoon
:

Continue your journey along the trail, taking breaks to observe the diverse wildlife that inhabits the area. After a few hours of biking, enjoy a picnic lunch at one of the many scenic overlooks or parks along the way. If time allows, consider taking a nature walk to learn more about the local flora and fauna.

evening
:

After a day of adventure, return to Cumberland for a relaxing dinner at a restaurant with a cozy atmosphere. Share stories of your day’s discoveries while enjoying a meal that features locally sourced ingredients. End your evening with a leisurely stroll through town to take in the night lights and the charm of Cumberland.

day 8
Historical Sites and Civil War Heritage
morning
:

Begin your day at the historic Fort Cumberland, where you can step back in time and learn about the military history of the area. Enjoy a guided tour that provides insights into the fort's role during the French and Indian War. Afterward, grab breakfast at a nearby café that offers a selection of hearty options.

afternoon
:

In the afternoon, visit the nearby C&O Canal National Historical Park to explore its historical significance and view the preserved locks and structures along the canal. Take a leisurely walk along the towpath, imagining the lives of those who traveled this route in centuries past. Stop for a scenic lunch at one of the picnic areas surrounded by nature.

evening
:

As evening approaches, head back to Cumberland and dine at a restaurant that offers a menu rich in local history and flavors. After dinner, take a historic ghost tour of the city, where you can hear eerie tales and legends from Cumberland's past. Conclude your day with a nightcap at a local establishment, reflecting on the history you've uncovered.

day 9
Relaxation and Wellness Retreat
morning
:

Start your day with a peaceful yoga session at a local wellness studio, allowing yourself to unwind and center your mind. Follow the session with a nutritious breakfast at a health-focused café that serves fresh smoothies and wholesome dishes. Take a moment to enjoy the serene atmosphere before embarking on your day of relaxation.

afternoon
:

In the afternoon, treat yourself to a spa experience at a local wellness center, where you can indulge in massages, facials, and other rejuvenating treatments. After your pampering session, enjoy a light lunch at a nearby café that emphasizes fresh, organic ingredients. Spend some time exploring local boutiques that offer wellness products and artisanal goods.

evening
:

As the evening sets in, enjoy a calming dinner at a restaurant that specializes in healthy cuisine. After your meal, attend a local meditation or mindfulness session to further enhance your relaxation. End your day with a peaceful walk through a local park, reflecting on your wellness journey and appreciating the tranquility of the surroundings.

Discover Cumberland

Read more in our Cumberland 2025 Travel Guide.

Cumberland Travel Guide