How long do you have. You can really get a good variety by a few towns along the coast and take trains. New Haven and get some famous pizza and see a small college town. Bars and restaurants.
Mystic Seaport for quirky fun history and the Aquarium is one of the bests. For extra time there some cool historic stuff along the way like in Lyme. Art musuem and such.

If in summer go on a fishing trip with the Blackhawk. Super fun and we have fantastic ocean fishing.

The casinos are unique so could be worth a visit. The Native American musuem at Foxwoods is fantastic. I like vibe of Mohegan.

We have beautiful nature too so plenty of hikes but I'd have to look for accessible ones.

You seem like my kind of traveler. It's how I do it too.

Enjoy and feel free to reach out.