The Essex Steam Train & Riverboat offers a 2 1/2-hour train and riverboat experience through the historic 1892 Connecticut River Valley. They also have a dinner train, which features a 4-course meal in a 1920's locomotive, and a unique rail biking experience, where you bike 8 miles round trip on the train tracks. This is a favorite date activity of ours. We recommend booking in advance!
Another favorite date activity of ours, Gillette Castle State Park has it all--hiking, a historic castle built by an eccentric actor, incredible water views, and the option to take a ferry ride. The park also features a cafe, and occasionally, food and ice cream trucks in the parking lot! The park and its grounds are free, but tickets to tour the castle are $6/each.
There's so much to do in New Haven. Some of my top recommendations are the Yale Art Gallery (free!), and the Yale Peabody Museum (where we had our first date!). You could also stroll downtown / around Yale's campus, and eat at any of the amazing restaurants. One of our favorite restaurants is Skappo, especially if you're looking for authentic Italian food straight from nonna. We also love Geronimo's (Mexican), Olives and Oil (Italian), Via (tapas), and Bar (pizza).
Mystic is a historic sea port town about a 45 minute drive from our venue. There are two walkable downtown areas, Mystic, and the Mystick Village, with shops, restaurants, and beautiful river views. There's also an aquarium and museum.
Hartford is Connecticut's capital city. There's lots to do nearby, especially if you're interested in venturing outside of the city to West Hartford, where there are several walkable streets and wonderful restaurants. Our favorites in that area are the Wadsworth Athenaeum (art museum), and Elizabeth Park (outdoor gardens). Some of our favorite eats include Bears (Southern BBQ), and Sparrow (pizza and bar food).