Depends on their interests. I remember it being pretty boring being a teen in the Hartford area. That’s a tough age gap in some ways - about the same as my sibling and I. It’s like one is too old and the other is too young, and it’s hard to find things that would be interesting to both.

We have some cool outdoor places to explore. The rail trail along the CT River is fun. If they’re into hiking, look at some the land trusts in the region.

You could drive or take a train to New Haven. Walk around Yale campus, walk through the free museum, grab some food, check out some stores. Go to Edgerton Park, check out the free greenhouses. The older brother might like Strangeways. New Haven feels more like a city and I loved that stuff as a kid.

Alternately, head north to Basketball Hall of Fame, or maybe check out Northampton, Easthampton, Amherst.

Or check out Mystic Aquarium.