- Our list of the best things to do in Oak Bluffs, Massachusetts, features the top 233 nearby activities — including 102 great attractions with user approval ratings of 90% or more!
- Oak Bluffs, MA has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Museums & Galleries, Sights & Landmarks, and Water Activities.
- The results below include the top 25 things to do within the city of Oak Bluffs, MA , followed by 207 popular activities in nearby cities, including Edgartown, Hyannis, Barnstable, New Bedford, Sandwich, Vineyard Haven, Woods Hole, South Yarmouth, Mashpee, Wareham, West Yarmouth, Dartmouth, Chilmark, West Tisbury, Plymouth, Gay Head and Menemsha
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36.7 Miles
Purgatory Chasm is a chasm formed by glaciers thousands of years ago. The chasm is about 10 feet wide, 120 feet long, and 50 feet deep. Visitors will find a small bridge over the chasm offering an unobstructed downward view.
36.8 Miles
Blue Claw Boat Tours is a local company which offers custom boat tours on Cape Cod which include sightseeing seal cruises, oyster farm and critter tours, beachcombing trips and more.
36.8 Miles
Bowling, dining and a full bar are offered at Orleans Bowling Center. Guests can select from a barbeque menu and 16 available beers on tap. Arcade games are also part of the fun.
36.8 Miles
Located next to Maidford River, Paradise Valley Park features a windmill built in 1810 and is home to local community events. The park provides a walking trail, picnic tables and benches as well as grassy and wooded areas.
36.9 Miles
Orleans, Massachusetts is home to the Academy of Performing Arts. This prestigious arts institution is dedicated to dance, visual arts, musicals, straight plays, opera and other forms of artistic expression.
36.9 Miles
Located in the restored and preserved historic home of Bishop George Berkeley, the Whitehall Museum House contains art and items of historical interest. A series of philosophical lectures is hosted there, as well, in honor of Berkeley's tradition.
37.0 Miles
Escobar's Highland Farm is a working farm open to the public. Its highlight is an 8 acre corn maze, which has a unique design each year, and visitors can also go on hayrides and explore a large pumpkin patch.
37.0 Miles
Guests can enjoy a play center that features the Eyeplay gaming platform that projects graphics and sounds onto floors and walls at Kidventure Play & Party Center. The center is also available to host birthday parties.
37.2 Miles
Middletown, Rhode Island is home to the Newport Vineyards, an expansive vineyard, winery and event venue. The winery offers two tours every day and invites visitors to its tasting room for samples of its finest wares. Bottled wines are sold in the adjacent shop.
37.3 Miles
Church of the Transfiguration belongs to a local Benedictine monastic community called Community of Jesus. The church features 4th-century architecture decorated with numerous handcrafted frescos, mosaics and sculptures made of bronze, glass and stone.