- Our list of the best things to do in Cheshire, Connecticut, features the top 451 nearby activities — including 186 great attractions with user approval ratings of 90% or more!
- Cheshire, CT has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Museums & Galleries, Entertainment & Shows, and Sights & Landmarks.
- The results below include the top 10 things to do within the city of Cheshire, CT , followed by 441 popular activities in nearby cities, including New Haven, Hartford, West Hartford, Hamden, Middletown, Wallingford, Bristol, Waterbury, Milford, Branford, Newington, Guilford, Wethersfield, New Britain, Farmington, Torrington, Bloomfield, Madison, Southington, Trumbull, Stratford, West Haven, East Haddam, Woodbury, Litchfield, Southbury, Avon, Clinton, Shelton, Glastonbury, Meriden, New Hartford, East Hartford, Simsbury, Naugatuck, Washington Depot, South Windsor, Plantsville, Mashantucket, Windsor, Manchester, East Haven, Washington and Goshen
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40.0 Miles
85%
363 votes
102 West Broadway, Port Jefferson, NY 11777
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Visitors enjoy the ease of travel with the Bridgeport and Port Jefferson Steamboat Company. The company offers ferry rides along Long Island Sound, making traveling the area simpler as well as offering beautiful scenic views.
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Guided individual tours of the Mather House Museum are held during opening hours which covers period furniture and paintings, vintage tools, model ships, and antique toys and dolls. The building is also the headquarters of the Historical Society of Greater Port Jefferson.
40.0 Miles
The Fireboat Firefighter Museum documents the history of fireboats and firefighting in New York City. The museum is located in a real working fireboat that operated for over 70 years in New York's harbor before being retired.
40.0 Miles
93%
59 votes
234 Carpenter Street, Greenport, NY 11944
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Greenport Harbor Brewing Co. is a small craft brewery that focuses on providing beer made with a base of the common hop. The brewery sells roughly 14 specific beers and has an on-site tasting room.
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The Mijoy 747 is an 85 foot fishing ship used for private deep sea fishing charters. The ship is outfitted with up-to-date electronics and equipment and features an experienced crew open to answering any questions customers may have.
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Located on the Niantic River, Niantic Bay Marina Boat Valet is a marina offering a number of amenities for boat owners to enjoy. Indoor rack storage for boats, a repair facility, and a marine store are among the amenities available.
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North Folk Wine Tours is a wine tour company that offers bachelorette party tours, birthday party tours, limo/party bus tours, and team building events. The company can accommodate tours up to 200 people.
40.0 Miles
60%
5 votes
Long Island Wine Council, 5120 Sound Avenue, Riverhead, NY 11901
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With over 30 wineries located in the region, Long Island Wine Country offers visitors a chance to sample a wide selection of wine produced in the area. There are also many farm stands where visitors can purchase fresh produce.
40.0 Miles
100%
3 votes
Prestons Dock, 120 Main Street, Greenport, NY 11944
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A charter boat and tour company, Greenport Electric Launch Co features the Glory, a boat that has been converted completely to solar power. Visitors can learn about and ride on the ship on a variety of cruises.
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Providing direct access to Greenport Harbor, Mitchell Park & Marina offers a dock that can board a variety of boat sizes. The marina is located next to a park with a boardwalk and carousel.