Top 10 things to do in Middletown, Connecticut



Middletown, Connecticut has a lot to offer. From outdoor adventures to scenic train rides, dinosaur parks, and of course, celebrity homes, Middletown has a plethora of things to do that everyone can enjoy.

Embark on an unforgettable journey on the Essex Steam Train

Lasting approximately two and a half hours, the Essex Steam Train offers a narrated round trip through the heart of the unspoiled Connecticut River Valley. The vintage locomotive chugs through the tidal wetlands of Chester Creek and Pratt Cove and offers unique access to several coves.

Immerse yourself in an on-board eco-excursion as you discover birds like Greenland Geese, Egrets, Blue Heron and Red-winged Blackbirds in their natural habitats. Catch the spectacular site of the majestic Bald Eagle migration in February and March.

Spend a day in a writer’s shoes at Mark Twain’s House

Tour the home of America’s greatest author and cultural figure, Samuel Clemens, also known as Mark Twain. This National Historic Landmark is the restored home where the author and his family lived from 1874 to 1891. Named by National Geographic as “one of the most historic homes in the world”, The Mark Twain House and Museum is definitely Instagram worthy.

Explore the handsome Billiards room where Twain wrote his famous books The Adventures of Tom Sawyer, The Adventures of Huckleberry Finn, and The Prince and the Pauper. Marvel at the stick-style architecture of the 25-room home that features a lush glass conservatory, a dramatic grand hall, and a library.

The museum offers a budget-friendly lunch at the Nook Café and the store offers exclusive Victorian gifts, souvenirs, memorabilia, and books for readers of all ages.

Dare to defy the Brownstone Exploration and Discovery Park

Outdoor adventurers should gear up for the Brownstone Exploration and Discovery Park, spending a summer day maneuvering insane, water-based obstacles. The inflatable water park features 11 zip lines, an ‘extreme’ rope swing, cliff jumping, rock climbing, wakeboarding, kayaking, and paddleboarding.

You can rent everything you may need from snorkeling gear, wetsuits, a floating gazebo to a large private dock. There are food and snack shacks located throughout the park as well as a general/apparel store with all the necessities for a fun-filled day in the sun.

Get airborne at the New England Air Museum

Take a stroll through aviation history at the New England Air Museum. Stacked with over 100 aircraft ranging from early flying machines to supersonic jets, the museum will thrill aircraft enthusiasts of all ages.

Immerse yourself in the aeronautics world with featured activities such as ‘build and fly challenges’, flight science demonstrations, aircraft quest scavenger hunts as well as personalized tours of selected aircraft cockpits like the Douglas A-26C ‘Invader,’ and Kaman SH-2F ‘Seasprite’. 

The Museum is situated over three large exhibit hangars and there is an outdoor display area when the weather allows. The library spans over two floors and showcases aviation books and technical manuals, photographs, and artworks of aircraft and several personal collections related to WWI and WWII aviation history.

Have a Jurassic moment at the Dinosaur Place

Relive the Mesozoic Era at the Dinosaur Place at Nature’s Art Village. This 60-acre outdoor adventure park houses over 50 life-sized dinosaurs scattered on pristine nature trails. Work as a paleontologist at a replica dig site, get lost and found in the mammoth-sized A’maze’asaurus with twists and turns bordered by identical white panels. Finish off the day at New England’s largest Splash Pad that boasts over 30 dinosaur-themed features.

Watch out for the ground sensors that activate the ‘flying’ Pteranodon, and from October catch the goblins, ghouls, and mythical creatures of five spooky Halloween experiences along the Raptor Bay Trail. Challenge yourself at the 18-hole tournament-style golf course built to resemble the theme of a one-of-a-kind Old West Mining Town.

Trek to the Seven Falls State Park

If jumping over boulders and scrambling uphill over weeds gets your blood pumping, then the rugged trail to the Seven Falls State Park is a great workout for hikers and nature lovers. 

Located on the outskirts of the southern end of the city, the 3.7-kilometer (2.3 mile) loop trail winds its way through the wooded environment close to the Connecticut River, leading to a series of small cascading waterfalls. The trail is full of surprises and may be slightly difficult for dogs and young children. There are specific areas set up with picnic tables for an ‘on-the-way’ snack break as well as marked trails for short to medium hikes. 

Learn about the Middletown Community at General Mansfield House

From major exhibits showcasing artifacts from the Historical Society’s permanent collection, the museum at General Mansfield House will give you a sneak preview into the history of Middletown.

Live through the experiences of local soldiers in the Civil War by examining letters, diaries, photographs, and military gear. Explore artifacts from World War I, follow the advances of 19th-century women’s clothing, and examine the rise and fall of manufacturing in Middlesex County.

Discover the small town with a big telescope

Find out what is written in the stars at the Van Vleck Observatory. Located at the highest point on the campus of Wesleyan University, visitors are welcome to attend interactive presentations by astronomy majors and faculty on space news. If the weather permits, visitors can observe the sky through the telescopes.

The Van Vleck Observatory is fitted with three telescopes. Public observation nights make use of the 16-inch (40.64 cm) and 20-inch (50.8 cm) telescopes. The third telescope is the 24-inch (60.96 cm) Perkins Telescope that is one of New England’s largest telescopes and is mostly used for research purposes.

Cruise around the Dart Island State Park

Take a boat ride to the Dart Island State Park that is technically situated on a sandbar island in the middle of the Connecticut River. The park consists of nineteen acres of undeveloped land and is only accessible by boat.

Be at one with nature while bird watching, as you drift through a myriad of ‘typical river trees’ including willow, poplar and red maple. Dart Island State Park is an ideal local’s hotspot for swimming, fishing, water sports and volleyball.

Indulge in a red or white sundowner

Take a vino-inspired tour of Arrigoni Winery where you get to sample an extensive selection of traditional and specialty wines, including Cabernet Sauvignon, Malbec, Merlot, Sauvignon Blanc, and Pinot Noir.

Enjoy friendly conversation and weekly live music under the umbrella-tabled patio. Sip 20 varieties of wine in the covered pavilion with outdoor heaters and a fireplace. When the weather gets frosty, warm up with delicious wines at the rustic tasting room and indoor seating area. Don’t forget to pick up your souvenir wine glass after your tour.