- 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
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.
17 Howard St, Cumberland, MD MoreLess Info
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.
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.
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.
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White Oaks Shopping, 1649 Oldtown Road, Cumberland, MD 21502 MoreLess Info
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.