Middletown is a small city in Middlesex County, Connecticut, with an area of just around 40 square miles.
What the city lacks in size is recouped by its quintessential New England charm that unlocks plenty of exciting activities.
English settlers established it as a town in 1651 and named it after the local indigenous people Mattabeseck.
Two years later, the Middletown name was adopted, descriptive of its location between Hartford and Saybrook along the Connecticut River.
Middletown was incorporated as a city in 1784, achieving growth initially as a sailing port on the west banks of the Connecticut River.
The city later became an industrial center but eventually turned largely residential.
The 1831 establishment of the Wesleyan University in Middletown contributed much to this shift and the city’s emergence as an interesting place to visit.
Find out the top attractions of this city on this list of the best things to do in Middletown.
Explore the Wadsworth Falls State Park
Adjacent to Long Hill Estate, Wadsworth Falls State Park spreads over 267 acres and offers opportunities for hiking and biking on its meandering trails.
Its crown jewel, Wadsworth Falls, is located on the park’s southwestern side and formed by the cascading waters of the Coginchaug River.
This river is a popular canoeing route as it flows onward into the Mattabesset River’s tidal marsh.
Like its neighboring Parklands at Long Hill, this park features lush woodlands with a giant laurel tree as one of its landmarks.
The park also offers a picnic area and a pond where visitors can swim under the canopy of leafy trees.
Visitors of Wadsworth Falls can extend their exploration north to the half-acre Frank S. Marszalek Park near Starr Millpond and Covered Bridge.
Enjoy the River View at Harbor Park
Harbor Park spreads over 2.6 acres and offers visitors an extensive pathway along the banks of the Connecticut River.
Along this riverwalk, you can savor refreshing views of the river and the graceful curves of the Arrigoni Bridge across it.
The park on Harbor Drive provides a dock to launch boats into the river and has fishing spots.
Right off the city’s Main Street, you can access the trail to this park, where a playground and picnic facilities are also available to visitors.
Some public art pieces in Middletown are displayed in this park on Harbor Drive, including a sculpture of Christopher Columbus.
Additionally, a Middletown Lions memorial honoring military veterans is also located in this park.
Visit Dart Island State Park
Dart Island State Park is a large sandbar along the Connecticut River on the southeast side of Middletown.
This park is accessible only by boat, which you can launch from Middletown’s waterfront Harbor Park in the north.
Dart Island State Park offers opportunities for birdwatching and fishing on the Connecticut River.
Fishing on this river can be enjoyed year-round, and anglers can resort to techniques like fly fishing, spin fishing, bait fishing, and ice fishing.
Potential catch on the Connecticut River includes Trout, Bass, Striped Bass, Pike, and Carp.
There are no public facilities in the Dart Island State Park, but you may access those in its nearby city park.
Browse the Artifacts of the Greater Middletown Military Museum
Visit the Greater Middletown Military Museum on Walnut Grove Road and see the memorabilia of those who have served in the U.S. Armed Forces.
Admission to this museum at Veterans Memorial Park is free for visitors of all ages.
The museum’s military memorabilia collection includes artifacts from all branches of military service.
Local veterans and their families donated these artifacts to the museum.
The artifacts include medals, weapons, uniforms, flags, photographs, documents, letters, and books, among other items.
The museum’s grounds draw attention, too, with its Huey chopper used during the Vietnam War and a monument of the Secret Guerilla Unit.
The Connecticut Trees of Honor Memorial Park, a tribute to the state’s KIAs in the Iraq and Afghanistan conflicts, is also adjacent to the Greater Middletown Military Museum.
Bring Your Toddlers to the Kidcity Children's Museum
The Kidcity Children’s Museum is a fun attraction for kids on Washington Street.
Children one to eight will enjoy this three-story museum, where they can see many exciting exhibits and pretend to be their favorite grown-ups in imaginative play.
All the Kidcity Children’s Museum exhibits are handmade and unique, which in-house artists crafted to inspire kids’ playfulness.
Kids can play in themed exploration areas like a pirate ship, underwater cave, farm, and fishery.
Tour the Wadsworth Mansion
The Wadsworth Mansion is a historic residence at the 103-acre woodlands of Long Hill Estate in the rolling hills of western Middletown.
A local businessman and philanthropist, Colonel Clarence S. Wadsworth, built it as a summer home in the early 1900s.
The City of Middletown owns this mansion on Wadsworth Street, with the Long Hill Estate Authority operating it.
The mansion is open by appointment for guided historical tours on Wednesday afternoons.
During the Wednesday tours, you will see up close the outstanding classical revival features of this 16,000-square-foot mansion,
The points of interest include the vintage furniture that the Wadsworth family donated and is now displayed in the mansion’s History Room.
The tours on second Wednesdays are special, as, on these days, visitors can have tea and goodies in the tradition of the mansion’s fabled hospitality.
Watch out for special events, like outdoor bazaars and performing arts presentations held seasonally at the mansion.
Step Back in Time at the General Mansfield House
Take a closer look at U.S. history by visiting the General Mansfield House on Main Street.
During the 1950s, the Middlesex Historical Society saved this 1810 Federal-style home from demolition.
The historical society restored and converted it into a museum and as its headquarters.
Gen. Joseph King Fenno Mansfield of the Union Army was the original owner of the General Mansfield House, which is now aptly the home of Civil War artifacts and other memorabilia.
The past rotating exhibits of the museum included World War I artifacts, 19th-century clothing Middletown’s 19th-century ladies, and varied immigrant groups.
Besides its museum exhibits, the historical society hosts re-enactments of Colonial War battles, walking tours, and a lecture series.
Many visitors and locals also look forward to the society’s Annual Antique Car Show and Flea Market, typically set in October each year.
Join an Event at The Buttonwood Tree
The Buttonwood Tree is a unique performing arts center on Main Street at Middletown’s fabled North End.
It started out as a shop for used books and a performance space in 1989 and grew to host over 250 cultural events annually.
A nonprofit, North End Arts Rising, Inc., runs The Buttonwood, resulting in free or affordable entertainment and cultural enrichment.
Its funds are drawn from box-office donations, state and local arts grants, individual contributions, foundation grants, and book sales.
The events that this venue hosts include musical concerts, exhibits, literary readings, and storytelling.
The Buttonwood Tree also accommodates educational programs for leading artists in dance, theater, art, literature, and poetry.
Watch the Teen Talents of the Oddfellows Playhouse
The Oddfellows Playhouse Youth Theater is located on Washington Street, just a short walk from the Kidcity Museum and Harbor Park.
This theater presents high-quality shows of young people from multiracial and multicultural backgrounds.
Most playhouse productions resulted from repertory programs for ages 12 to 14 and 14 to 20.
The theater’s talents are drawn from over 2,500 youngsters living in central Connecticut.
Oddfellows Playhouse is especially popular for its Annual Children's Circus of Middletown, held from July to August, with a finale performance at the end of the season.
Swing at Vinnie’s Jump and Jive
Get to the dance floor of Vinnie’s Jump and Jive at either Washington Street or Main Street.
Fear not, even if you're not good at dancing, as this dance studio goes by its adage, “All Kinds of Dance, All Kinds of People.”
It has about a dozen seasoned instructors to see you through any dance moves.
Vinnie’s Jump and Jive offers open sessions and lessons in country line dancing, swing dancing, salsa mambo, hip-hop, tango, and more.
Attend its Swing and Blues Dance on Saturdays when a live band provides the dancing tunes.
Shop at Main Street
Turn to the corridor of Main Street and its east extensions to shop for souvenirs and sample the local cuisine.
This district hosts a wide variety of shops like Bob’s Stores, popular for its discounted apparel and footwear.
Children’s gifts can be sourced from Amato’s Toy and Hobby on Middletown’s Main Street near the KidCity Museum.
Drop by the mini-mall Main Street Market with a wide range of stores and restaurants for one-stop shopping and dining.
Union Green, a pocket park on the corner of Main and Pleasant Streets, hosts Middletown’s seasonal farmers market from June to October.
In these months, shoppers enjoy bargains on fresh local produce from late morning to early afternoon on Fridays.
Catch a Show in the Wesleyan Center for the Arts
Wesleyan University banners the superiority of its program on Visual and Performing Arts via events at this school’s Center for the Arts.
Located on High Street at the university’s north campus, the center hosts 300 events yearly.
These events include art exhibits and music, dance, and theater performances.
The Center for the Arts presents not only the works of its faculty and students but also the work of guest artists.
One of CFA’s regular annual events is Navaratri, a celebration of India’s diverse music and dance.
Order Breakfast or Lunch at O'Rourke's Diner
Relish a gourmet breakfast or lunch at O'Rourke's Diner, a classic boxcar diner on North Main Street.
Established in 1941, this unique restaurant features a mini-jukebox at each booth.
The restaurant’s varied menu offers dishes of strong Irish influence and traditional American recipes.
Try the four-course Specialty Dinners of O’Rourke flaunting fresh salad, homemade soup, an exquisite entrée, and dessert.
There’s also live music during these special events, so check out O'Rourke's Diner on your trip to Middletown.
Stroll on the Parklands at Long Hill
The Parklands at Long Hill is the 103-acre lush, wooded area around the historic Wadsworth Mansion.
It features a two-mile dual trail open daily to the public from sunrise to sunset, providing a full view of the mansion dubbed “the gem of Middletown.”
Hikers exploring the trails will also enjoy walking under the canopy of white oaks and curved brownstone walls.
More than 20 tree species were planted around the mansion, including the Amur Cork Tree native to China and designated in Connecticut as a notable tree.
Informative plaques called “Tales along the Trails” have been installed along the Parklands’ footpaths to tell hikers the story of the Long Hill Estate.
Trail brochures about the history of the estate and the Wadsworth family are available at a kiosk at the trails’ entrance.
Go Organic at It's Only Natural Market
A large health food store, It's Only Natural Market is located on Main Street and specializes in fresh organic produce.
This retailer is a must-visit for vegetarians and vegans.
Besides meeting their dietary needs, this organic grocery store can also supply them with a wide variety of wellness, health, and beauty products.
This store likewise runs an adjacent cafe offering salads, smoothies, and nutritious juices.
Another organic menu choice comes from the nearby ION Restaurant, a vegans’ favorite in central Connecticut for over 30 years.
Besides its organic and imaginative dishes, It's Only Natural Market offers gluten-free food options and creative cocktails.
Middletown offers plenty of fun attractions and activities for all kinds of travelers.
This city's main points of interest are all within arms’ length reach, thus making for a very fulfilling visit.
Include these best things to do in Middletown, Connecticut, in your itinerary if you’re planning a trip to the state.