This Quiet Connecticut City Is Hiding In Plain Sight
Picture this: A morning spent hiking waterfalls and stone ruins, followed by a New York-style pizza slice for lunch, and an afternoon at the military museum. Capping off the day, you can enjoy a sparkling drink at the local meadery. And it's all found right here in Middletown, Connecticut.
Situated on the Connecticut River, Middletown is a city of about 48,000 people. The presence of Wesleyan University helps drive the local culture, giving you plenty of things to do alongside the natural spots like the river and the waterfalls. However, it's easier to just show you what a visit here actually looks like. Let's dive into the specific attractions that make a trip to Middletown well worth your time.
Outdoor Recreation

Within a 15-minute drive from Middletown, you can reach waterfalls, ruins, and mountains, making for one of the most memorable hiking itineraries in Connecticut. The adventure begins at Wadsworth Falls State Park, where travelers can enjoy 4.5 miles of hiking and biking trails that lead to the park’s namesake waterfall. The Coginchaug River makes the park a great spot for fishing, and with swimming and picnic areas nearby, it is easy to spend the whole day outdoors.

Next up, you can check out the intriguing Spiderweed Preserve. This area is home to the stone ruins of a woman’s summer home, donated to the Nature Conservancy several decades ago. A 2.7-mile loop trail steadily climbs to the summit, where the ruins, once a two-story home, still stand with three outer walls slowly crumbling. Though just outside Middletown, Chauncey Peak lies only 15 minutes west and offers an invigorating hike. The trail winds along Chauncey Peak and Lamentation Mountain, passes Crescent Lake, and provides views of the Hanging Hills in the distance.
Arts & Culture

Middletown also has some impressive museums and theaters to check out during your trip. History lovers will definitely want to explore the Greater Middletown Military Museum, which preserves stories, artifacts, and documents from the soldiers who have served in the US Armed Forces.
If you are traveling with children, your family might enjoy a stop at the Kidcity Children's Museum, featuring themed rooms that encourage pretend-play. A few of the rooms inside include a fishery, a space-age road trip room, a toddler sea cave room, a Main Street, a farm, and a pint-size medieval village.

When the evening rolls around, you can grab a show put on by Artfarm, a theater company known for its focus on social justice and environmental sustainability. Depending on the time of the year, you might also catch a public exhibition at the Davison Art Collection at Wesleyan University, home to over 25,000 works of art.
Local Breweries and Meaderies

Middletown’s brewing scene is constantly evolving, with some fantastic breweries and meaderies to prove it. Forest City Brewing, located on Johnson Street, is a family-owned brewery that is open from Thursday to Sunday each week, specializing in NEIPAs, sours, and more.
Eli Cannon's Tap Room is a spectacular option on Main Street, serving only microbrewed beers and non-mainstream imports. IPAs, lagers, and porters are just a few of the craft brews you will likely find on tap. They also sell some hearty food options if you need a snack, including wings, wraps, and sandwiches.
Just around the block from Eli Cannon’s, you will find The Bergen House, a craft meadery that produces session meads, full-strength meads, and “meadtails.” Each month, the meadery also showcases work from a different local artist, so make sure to take a look around at the art during your visit.
Dining and Shopping

Middletown’s dining scene has gained a reputation for its diversity and creativity, with several restaurants offering unique experiences. Haveli India Restaurant is the first to have on your radar, a family-owned establishment specializing in Indian cuisine like lamb samosa, chili paneer, shrimp Manchurian, and chicken curry.
For some New York-style pizza, you can grab a bite at Mondo, which has been serving the community since 2010. Travelers seeking an upscale dinner, meanwhile, can make reservations at Osa, which features mouthwatering wood-fired small plates, cocktails, whiskey, and wine.
And, of course, no trip is complete without a souvenir. Fortunately, Middletown has the perfect boutique for your keepsake. The Handmade Hub showcases the work of over 75 local artisans and crafters, while Amato’s Toy and Hobby of Middletown sells art kits, puzzles, LEGOs, trains, toys, and more.
A Town To Rave About

It is never too early to start planning your spring or summer trips, and Middletown is one of those destinations that will fit into your itinerary perfectly. Families have plenty of options with waterfall hikes, the children’s museum, and toy stores, while adults looking for a laid-back weekend can stick to the breweries, meaderies, and ruins. Just about everybody will appreciate the culinary scene, which offers Indian food, pizza, pub fare, and more. You will likely be raving about the town by the end of your trip, too.