- 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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        32.5 Miles 
    
    
        
        
            Supfari Adventures Cape Cod is stand-up paddleboarding instruction combined with yoga and they offer various excursions on the lakes, including recurring classes. Their sessions typically last from 1.5 to 2 hours.        
    
    
        32.6 Miles 
    
    
        
        
            One of the most popular landmarks in Brewster, Massachusetts is the Brewster Store. This general-goods and grocery store was built in the mid-1800s and is still in business today. It also has an attached ice cream parlor called the Brewster Scoop.        
    
    
        32.9 Miles 
    
    
        
        
            Specializing in stand up paddle board rentals, Adventure Chatham offers visitors lessons on how to paddle through rivers and lakes. It also organizes sunset sight-seeing tours where visitors can paddle board with glow sticks.         
    
    
        32.9 Miles 
    
    
        
        
            Located along the scenic Cape Cod Bay, Breakwater Beach is a popular public beach among tourists and locals alike. The beach offers numerous tide pools, picturesque views, and ample parking spaces.        
    
    
        33.0 Miles 
    
    
        
        
            The Cape Cod Rail Trail is a popular biking path through the scenery of Cape Cod with the Rail Trail Bike Shop serving most visitors. They allow guests to rent their own bikes or arrange for package guided tours of the trail.        
    
    
        33.1 Miles 
    
    
        
        
            Cape Cod Rail Trail is a paved path leading from the town of Dennis to Wellfleet and is much used for biking, hiking and horseback riding. The trail follows an abandoned rail route and passes through a variety of landscape which comprises of woods, bogs, marshes and ponds.        
    
    
        33.1 Miles 
    
    
        
        
            An indoor/outdoor sports complex, Jungleplex maintains 60 000 square feet of playing space for activities including soccer, martial arts, field hockey and baseball, and also includes an arcade and cafe on the premises.        
    
    
        33.2 Miles 
    
    
        
            
        
                                    100%
                22 votes
                            
			
            
                
                391 Barn Hill Road, Chatham, MA 02633
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            Spend a day stretching your muscles on the water with Chatham Kayak Company - Guided Tours. The knowledgeable tour guides with lead the tour to areas populated by native wildlife and discuss the culture and history of the surroundings.        
    
    
        33.2 Miles 
    
    
        
            
        
                                    100%
                1 votes
                            
			
            
                
                Lafayette Road, Tiverton, RI 2878
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            With over 730 acres and 4 miles of trails, Wetamoo Woods & Pardon Gray Preserve is a great place for a hike or bird watching. Historic sites include an abandoned saw mill, stone bridges, and gray cemetery.        
    
    
        33.3 Miles 
    
    
        
        
            A part of the Nantucket Island, Sankaty Head Lighthouse is a historic structure dating back to late 19th century and operates as a scenic overlook today offering beautiful views of the shoreline and the ocean.