Fair. Madison ranks 16 in state, Guilford is right behind at 19. Definitely assumptions I made based on what I saw

I grew up in Madison (graduated 2013) and had a friend group in Guilford, here's my honest assessment.

Madison is overall a better school system and might bode better with in state colleges. Madison oozes athletics and sports, is a bit richer and preppier. Vineyard Vines people.

Guilford seemed a bit more arts focused, almost more hipstery. There's a bunch of recording studios in Guilford, not so much in Madison. Still a similar type of person I'd reckon, but less stuck up.

At the end of the day either are more similar than different, Guilford being a bit cheaper from a real estate perspective. I can't say I enjoyed growing up there though.

New Haven is the ONLY Connecticut city on the map in terms of outside interest. Without Yale, New Haven is nothing. CT is lucky to have such a top notch ivy league and medical brand in its borders. Its not perfect for the area, but look at Bridgeport or Hartford 🤷‍♂️