Consider spending a day in the beautiful Watch Hill, RI. Home to Nappatree Point, The Ocean House, and one of Taylor Swifts homes. While during the peak of the summer parking can be slim, September will be a wonderful time to experience the Rhode Island beaches. Kristina grew up spending time at Watch Hill Beach with her Baba eating ice cream and riding the carosel. Drive up the road a bit and grab a sandwich at The Cooked Goose... you won't be dissapointed.
Consider spending some time in Rhode Island. Narragansett Beach in September will be free admission so take advantage of the free parking, clean beaches, and close proximity to dining at The Coast Guard House. The calamari at Coast Guard is one of our favorites!
Catch a Worcester Red Sox game. While the Boston Red Sox will be away at NY playing the Yankees, consider catching a Woo Sox game.
Consider taking a day trip to Block Island. Ferries are a bit more limited in September from nearby New London Port, but Friday or Sunday consider taking a day trip to explore what the island has to offer such as renting a bike, shopping, catching a bite to eat, experiencing the Block Island Exotic Animal Farm, and seeing the Mohegan Bluffs