- Our list of the best things to do in Oakland, Maryland, features the top 30 nearby activities — including 16 great attractions with user approval ratings of 90% or more!
- Oakland, MD has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Entertainment & Shows, Sights & Landmarks, and Amusement.
- The results below include the top 16 things to do within the city of Oakland, MD , followed by 14 popular activities in nearby cities, including Davis, Grantsville, Cumberland and Medley
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38.2 Miles
At the bottom of the railway depot is the Cumberland Visitor Center. The first floor is the visitor center and C&O Canal National Park museum, and on the second floor is the lobby for the Western Maryland Scenic Railroad.
38.2 Miles
Western Maryland Scenic Railroad is a heritage railroad which operates between Cumberland and Frostburg offering scenic train rides to passengers with the help of their steam and diesel locomotives.
38.2 Miles
17 Howard St, Cumberland, MD
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From dry to semi-sweet to sweet selections, the Charis Winery offers visitors a well-rounded wine tasting experience. Their grape and fruit varieties will tickle the palates of connoisseurs and everyday tasters alike.
38.2 Miles
Located off of the I-86, Sidling Hill Overlook & Rest Area offers visitors a scenic walking bridge that crosses over the highway. From the bridge, visitors have panoramic views of the surrounding hills and rock structure.
38.2 Miles
With flashlights, visitors can explore the brick tunnels of C&O Canal Towpath. Other structures that can be seen in the canal include lift locks, lock houses, feeder dams, waste weirs, and culverts.
38.2 Miles
An art deco-styled, vintage 1930s-style theater, the New Embassy Theatre hosts a wide variety of entertainments. Cumberland's oldest theater, it shows films as well as hosting live drama, burlesque shows, and a variety of live musical performances.
38.5 Miles
Winding through Elkins natural beauty is the Allegheny Highlands Trail. The trails, popular for walking, jogging and cycling, offers picturesque views that change with each season and runs over twenty-six miles.
38.6 Miles
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White Oaks Shopping, 1649 Oldtown Road, Cumberland, MD 21502
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A 32 lane bowling alley with 8 wood and 24 synthetic lanes, White Oak Lanes also features a pro shop, video games and a full-service snack bar. They have numerous specials, leagues and party packages.
38.8 Miles
See the latest and greatest feature films at Carmike Cinemas in Uniontown. The theatre is equipped with closed captioned technology. A concession stand is available. Child, matinee and senior rates are offered.
38.9 Miles
Alpaca in the Moon Farm is home to small alpaca herds including Suri and Huacaya varieties, and they specialize in alpaca fiber, sales and breeding. The farm hours vary so appointments are recommended.