- Our list of the best things to do in Westport, Connecticut, features the top 290 nearby activities — including 110 great attractions with user approval ratings of 90% or more!
- Westport, CT has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Entertainment & Shows, Museums & Galleries, and Sights & Landmarks.
- The results below include the top 13 things to do within the city of Westport, CT , followed by 277 popular activities in nearby cities, including Norwalk, Stratford, Ridgefield, Fairfield, Bridgeport, Stamford, Danbury, Milford, Port Jefferson, New Haven, Greenwich, White Plains, Trumbull, Smithtown, West Haven, Shelton, Glen Cove, Southbury, Huntington Station, Port Chester, Commack, Plainview, Coram, Cooperstown and Carmel
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1415
46.5 Miles
The Peconic Bay Winery was founded in 1979 and offers an extensive variety of wines, hard cider, and grape brandy. Outdoor live entertainment is presented during the summer months and harvest season, but the actual tasting room is located off-site.
46.5 Miles
A reservoir that supplies water to Newburgh, Chadwick Lake has walking trails, a playground, picnic shelters and basketball courts. Visitors can fish and boat on the lake, roller skate in the rink area, and walk dogs on the trails.
46.5 Miles
87%
15 votes
31855 Main Road, Cutchogue, NY 11935
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Coffee Pot Cellars Tasting Room is a small-production winery with connections to the beekeeping world that features beeswax and honey products in addition to their wines. They also occasionally host live music.
46.5 Miles
Producing 5 different varieties of wines, Coffee Pot Cellars is a winery that also makes handcrafted products including candles, crayons, and lip balm. The winery has a tasting room that is open Friday through Monday.
46.5 Miles
100%
5 votes
126 Degarmo Road, Poughkeepsie, NY 12603
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Open seasonally, the Overlook Drive-In Theatre Inc is an old-fashioned drive-in movie theater with contemporary digital video and sound. The theater shows a different movie each week, and runs a variety of promotions.
46.5 Miles
Founded in 1983 on farmland gravel, Palmer Vineyards was born. Now a sprawling area of vineyard, green hills and garden grounds, the winery and vineyard is appreciated by locals and tourists alike who come to sample the famous Robert Palmer wine.
46.6 Miles
1267
New Britain Museum of American Art
SPECIAL GROUPON DEAL: Up to 50% Off Admission at New Britain Museum of American Art
56 Lexington St., New Britain, CT
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Art lovers and history buffs always enjoy visiting the New Britain Museum of American Art in New Britain, Connecticut. This spacious museum owns impressive collections of paintings, drawings, sculptures and other creations made by American artists.
46.6 Miles
98%
1026 votes
2036 61st Street, Brooklyn, NY 11204
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Besides the varieties of pizza served during it, a Slice of Brooklyn Pizza Tour has other highlight too, since it takes the travelers to the Brooklyn Bridge, Coney Island, famous houses, and the locations for famous movies, such as Goodfellas and Annie Hall.
46.6 Miles
New Britain, Connecticut is home to Walnut Hill Park, a beautiful expanse of green land that is popular for strolling, picnicking and nature photography. Its amenities include a paved walking track, two tennis courts and a baseball diamond.
46.6 Miles
Offshore Sailing School offers lessons on how to sail on the open water for adults and their family. The courses taught by experienced sailors include topics that range from day sailing to cruising and racing.