CT is full of quaint little towns. If you're going along the coast, the area around where the Connecticut River meets the Long Island sound is my area
Lots of sweet towns with beautiful houses (there's so much old money in this area, it's stupid) and they all...ALL have some hidden gem of a restaurant or café or deli. Old Saybrook - Essex - Deep River - Chester - East Haddam area. Essex especially has a neat little downtown area to walk around and grab drinks at various pubs, plus one of the most famous New England Inn and Restaurants, the Griswold Inn. It's been operating as such since 1776. The area also boasts the CT river Museum, the Essex Steam Train, Gillette's Castle (it's actually a former home some rich old dude built to look like a castle that overlooks the CT River), The Goodspeed Opera House (no opera but super fun musicals comparative to Broadway), next to one of the only swing bridges left in the country. You can also take a schooner cruise up and down the river or an Eagle watch boat tour. Old Saybrook (5 mins away) has a lot of things too. Katherine Hepburn used to own a ginormous mansion out there (you can still see it if you find a local willing to point it out) but there's a small theater there named after her, the Kate. Super quaint little downtown with shops and many restaurants (lots of seafood!) and several coastal scenic drives that are half scenic for the water, half scenic for the mansions
So much pretty.
Plus it's all right around I-95 so not too far off the map, and most of it is visit-able all in a day or two. Plus, continue heading up I-95 another 20-30 mins and there's the beautiful USCG Academy on the Thames River, right across from Groton Sub Base (the USS Nautilus museum is super cool and would be thoroughly enjoyed by Monello) and another 10 minutes is Mystic CT - Mystic Seaport - that's a huuuggeee historical place with an awesome downtown for shopping, walking, drinking, and seeing. There's a museum for the seaport (used to do whaling out of this port), an old drawbridge, Mystic Pizza (where Julia Roberts got her start in THE movie), the Mystic Aquarium, and so many amazing restaurants, low-key and fine dining. I know a couple hole-in-the-wall places where you'll find the best Lobster rolls evah.
And I know you're not much of a casino person, but there's also the Mohegan Sun casino and Foxwoods both near the Groton/Mystic area. Supposedly the museum outside of Foxwoods is out of this world - the Pequot Museum. There were many indigenous tribes in that area, huge influence. But those casinos are very chill compared to the ones I've seen down here. They're geared to an all-inclusive experience. Many celebrities frequent them bc they're more low-key. And of course, dining is fantastic.
late August - mid-Oct is great for any and all these places bc the trees are filled in and it's not too muggy like it is in June/July. I'll stop now though, that's enough