- Our list of the best things to do in Trumbull, Connecticut, features the top 332 nearby activities — including 133 great attractions with user approval ratings of 90% or more!
- Trumbull, 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 Trumbull, CT , followed by 322 popular activities in nearby cities, including New Haven, Norwalk, Stratford, Ridgefield, Fairfield, Hamden, Danbury, Bridgeport, Stamford, Milford, Waterbury, Port Jefferson, Branford, Westport, West Haven, Woodbury, Southbury, Shelton, Wallingford, Cheshire, New Milford, Naugatuck, Smithtown, East Haven and Greenwich
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46.5 Miles
82%
51 votes
1071
Deep Hollow Ranch
Montauk Highway across from Theodore Roosevelt County Park, Montauk, NY
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The oldest working ranch in US, Deep Hollow Ranch offers its visitors horseback riding adventures on 3,000 acres of hills and beaches. The children can enjoy the Summer Pony Camp, and from the Trading Post can be bought souvenirs such as T-shirts and cowboy hats.
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
Featuring two annual prestigious performances, the Orange County Ballet Theater produces many professional dancers each year. The artistic directors are professionals and positions in the company are regarded with high esteem.
46.6 Miles
The best place to sample locally brewed beers, the Thomas Hooker Brewery is open during the weekends for beer sampling. This is also a great place to drink quality craft beer and, at the same time, meet local people.
46.6 Miles
Built in 1862 and being 2 stories high, the Flushing Town Hall is the home of the Council on Culture and Arts. Exhibition and public events, such as jazz concerts, are held in here. It is included in the National Register of Historic Places.
46.6 Miles
The pirate-themed Crow's Nest Mini Golf is a standard 18-hole course with a wide range of obstacles and features. Life-sized pirate statues stand next to several of the holes, and there is a cave with a waterfall.
46.6 Miles
Offering general walking and scenic tours Freeport's Nautical Mile has many fun and free forms of street entertainment. The site also features paid-for entertainment in the form of restuarants, shops, and a mini-golf course.
46.6 Miles
The Pinchot Sycamore Tree Park leisure park that is home to the Pinchot Sycamore, which is best known for being the largest tree in Connecticut. The park has trees that are estimated to be 200-300 years old.
46.6 Miles
Filled with wall to wall trampolines, Bounce Sports offers visitors a cardio fitness experience where they can jump across the facility. In addition to a foam pit, the facility has baskets for visitors to practice dunking on.
46.6 Miles
An entertainment center, Bounce! Trampoline Sports features activities that include open and foam pit jumping, dodgeball and slam dunk basketball. The center also provides party rooms, a foam pit, flat-screen televisions, arcade games and a snack bar.