I’ll add to the Middletown love, it’s a great place to live and a great place to visit. We have a 9-month-old and absolutely love taking him around town.
Breakfast at O’Rourke’s or cross the bridge to Sarah’s on Main in Portland, Coffee at Perkatory, take a walk down the harbor, your kid will love Amato’s toy store and RJ Julia bookstore next door to each other and there’s even a place called Kid City downtown.
Way too many lunch/dinner options to list here but Krust, Mondo, Celtic Cavern, Sicily and Whey Stationary are some of our favorites. Beers on the beach at Eli Cannon’s or a trip over to Stubborn Beauty/Spoke & Spy/Forrest City for brews, cider and a food truck.
Wesleyan’s campus is beautiful and very walkable with a baby in the summer, Wadsworth Falls is right there and there are a ton of trails in the area.