Hartford gets passed over a lot. People zip up I-91 on the way to Boston or jump off I-84 just long enough to grab gas, never realizing they're driving past one of the most underrated little capital cities in New England. That's a shame, because Hartford packs more history, art, and weird old charm into a few square miles than most cities twice its size. Mark Twain wrote his best books here. One of the country's oldest public art museums sits downtown.

Most people show up in Boston thinking they'll just walk the Freedom Trail, eat a lobster roll, and call it a trip. Then they lose three days — in the best possible way. Boston is one of those cities that keeps pulling you deeper. You wander into a neighborhood for lunch and suddenly you're standing in front of a church that predates the country. You duck into a market for coffee and end up staying for the afternoon.