15 Things To Do In Oakland MD

Things To Do In Oakland MD

Nestled in the picturesque Allegheny Mountains, Oakland, Maryland, is a hidden gem waiting to be explored. This charming town, with its rich history, stunning landscapes, and vibrant community, offers a plethora of activities for visitors seeking a unique and memorable experience. Whether you’re a nature enthusiast, history buff, or someone simply looking for a tranquil escape, Oakland has something to offer. Let’s dive into the diverse array of Things To Do In Oakland MD this enchanting Maryland town.

Things To Do In Oakland MD

  1. Explore Deep Creek Lake:

Oakland is home to the stunning Deep Creek Lake, one of Maryland’s largest freshwater lakes. Embrace the great outdoors by engaging in water activities such as boating, fishing, and paddleboarding. The lake’s serene surroundings also provide the perfect backdrop for a leisurely lakeside stroll or a relaxing picnic with family and friends.

  1. Discover Local Art and Culture:

Immerse yourself in the local art scene by visiting the town’s art galleries and cultural hubs. Oakland is home to various artists who showcase their talents through paintings, sculptures, and crafts. Take a stroll through the charming streets to explore the vibrant art community and perhaps even pick up a unique piece as a memento of your visit.

  1. Historical Exploration:

Uncover the town’s history by visiting landmarks like the Garrett County Historical Museum and the B&O Railroad Museum. These sites provide a fascinating glimpse into the area’s past, highlighting its role in transportation and industry. A walk through Oakland’s historic district will transport you back in time, with well-preserved architecture and stories waiting to be discovered.

  1. Outdoor Adventures:

For the adventure seekers, the surrounding mountains and parks offer an array of outdoor activities. Hike the trails of Swallow Falls State Park, where you’ll encounter picturesque waterfalls and lush greenery. During the winter months, Wisp Resort beckons with opportunities for skiing and snowboarding, ensuring year-round enjoyment for outdoor enthusiasts.

  1. Farmers’ Markets and Local Cuisine:

Delight your taste buds with the local flavors of Oakland. Explore the farmers’ markets, where you can sample fresh produce, handmade crafts, and regional delicacies. Additionally, the town boasts a variety of restaurants and eateries offering everything from traditional Appalachian cuisine to modern, eclectic dishes.

  1. Attend Local Events:

Check the town’s calendar for events and festivals that showcase the lively community spirit of Oakland. From music festivals to cultural celebrations, these gatherings provide a fantastic opportunity to connect with locals, experience the town’s dynamic atmosphere, and create lasting memories.

  1. Relaxation and Wellness:

Take a break from the hustle and bustle of everyday life by indulging in some relaxation. Treat yourself to a spa day or unwind in the peaceful surroundings of Oakland’s parks and gardens. Whether it’s a yoga session by the lake or a rejuvenating massage, prioritize your well-being during your visit.

  1. Golfing at Oakland Golf Club:

For golf enthusiasts, a visit to the Oakland Golf Club is a must. This well-maintained course surrounded by scenic views of the mountains provides a relaxing yet challenging golfing experience. Enjoy a round of golf while taking in the fresh mountain air and picturesque landscapes.

  1. Scenic Drives and Overlooks:

Embark on a scenic drive through Garrett County’s countryside, discovering hidden gems and breathtaking vistas. The town and its surrounding areas boast several scenic overlooks, offering panoramic views of the Allegheny Mountains and Deep Creek Lake. Pack a picnic and make a day of exploring the beauty that unfolds along these picturesque drives.

  1. Cultural Events at The Maryland Theatre:

Check the schedule at The Maryland Theatre for live performances, concerts, and cultural events. This historic venue hosts a variety of shows, from theatrical performances to musical acts, providing entertainment for locals and visitors alike. Immerse yourself in the arts and enjoy a night out in the heart of Oakland.

  1. Waterfall Chasing in Swallow Falls State Park:

Swallow Falls State Park isn’t just for hiking; it’s also home to some of Maryland’s most stunning waterfalls. Muddy Creek Falls, the state’s highest free-falling waterfall, and Swallow Falls are must-see natural wonders. Capture the beauty of these cascades and enjoy the peaceful ambiance of the park’s lush surroundings.

  1. Fishing and Boating Adventures:

Deep Creek Lake isn’t just for leisurely boat rides; it’s a haven for fishing enthusiasts. The lake is stocked with a variety of fish, making it an ideal spot for anglers. Whether you prefer casting your line from the shore or heading out on a boat, the fishing opportunities at Deep Creek Lake are abundant.

  1. Local Breweries and Wineries:

Sample the local libations by visiting Oakland’s breweries and wineries. Enjoy craft beers, ciders, and wines produced in the region while taking in the scenic views. Many of these establishments offer tastings and tours, providing a delightful experience for connoisseurs and those looking to explore the local beverage scene.

  1. Seasonal Festivals:

Oakland hosts a range of seasonal festivals and events throughout the year. From fall foliage celebrations to winter holiday markets, these festivals capture the essence of each season. Check the event calendar to coincide your visit with one of these festive occasions, and immerse yourself in the community’s joyous spirit.

  1. Mountain Biking and Trail Exploration:

Outdoor enthusiasts can explore the area’s rugged beauty on mountain biking trails. The surrounding mountains and forests offer a network of trails suitable for various skill levels. Rent a bike and traverse the scenic landscapes, experiencing the thrill of downhill rides and the satisfaction of conquering challenging terrain.


Oakland, Maryland, is a destination that seamlessly blends natural beauty, history, and community spirit. From the tranquil shores of Deep Creek Lake to the vibrant arts scene and outdoor adventures, there’s something for everyone in this charming town. Plan your visit to Oakland to create unforgettable memories and immerse yourself in the heart of Maryland’s Allegheny Mountains.

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