I live near Middletown and I’m in and out of there all the time. It’s a small city of almost 50,000 people. It has a bustling Main Street a few blocks from Wesleyan withe tons of restaurants, a multiplex movie theater, and a small live music venue, The Buttonwood Tree. There’s not much in the way of museums, but there are museums in Hartford, New Haven, and up and down the Connecticut Valley. You said that your son likes restaurants, movies, and museums. If you can be more specific about what else he likes, I can tell you what’s available.
I should note that Wesleyan has a student run farm if he likes that sort of thing. Students also volunteer in various ways in the community if he’s looking for that. There’s community theater in addition to what’s available on campus. There’s the best children’s museum anywhere where I’ve seen psych students doing research with children who have willing parents. There’s an active soup kitchen that’s always seeking volunteers. For a history buff, central Connecticut reeks with colonial and pre-colonial history. It’s also been home to writers like Mark Twain, Harriet Beecher Stowe, and Daniel Webster. It’s where Samuel Colt manufactured rifles and where modern aircraft engines are designed. Across the CT River in Portland are the old brownstone quarries where 90% of the brownstone for NYC, Boston, and Philadelphia was quarried. It’s now a zip line, rock climbing and water sport action and adventure park. Portland is also where the Airline Trail begins, a rails to trails project 25 years in the making, which runs across Eastern Connecticut for more than 60 miles and is shared by walkers, joggers, bikers, and horseback riders alike - basically any means of getting around as long as it’s not motorized. Portland is accessible by a short ride on local bus service.
There really is a lot happening in Middletown right now and there are lots of ways to get involved. The energy is coming from Ben Florsheim, the barely 29-year-old mayor who was elected just 2 years ago. He is bubbling with ideas and looking for ways to make them happen. Covid has changed things, closing some restaurants as it has everywhere, but Ben has convinced the city to buy one of them, an historic building on the river, and is turning it into a waterfront food court with plans for more to follow as one example of his efforts to keep the city thriving.
Ben is a 2014 graduate of Wesleyan and has mostly lived in Middletown since graduation except for a short stint in New Haven. You say that your son’s academic interests include government. Im sure that Ben will be very accessible to a Wesleyan student who is interested in getting some hands on experience with city government. Ben also worked with Sen. Chris Murphy for 5 years, so I expect that he has connections with that office for more experiences at that level as well. The senator maintains an office in nearby Hartford.
One example of Middletown’s community spirit is O’Rourke’s Diner, a vintage landmark going back 80 years. The O’Rourke family has run the diner the entire time. About 7 years ago the diner was devastated by fire. The O’Rourkes didn’t have to go to a bank to finance a rebuild. The community wasn’t going to let a beloved landmark die. Local citizen rallied and raised the necessary funds with donations from ordinary citizens. Be sure to stop and have a bite to eat there when you’re in town.
Really, lots happening and lots to do.