Smack dab in the middle of the state, the city of Hartford isn’t the prettiest introduction to Connecticut. In the middle of the 20th century, the city suffered as much of the middle class moved to a ring of suburbs around the city, taking their wealth with them. While nearby cities like Providence were able to revitalize their cores with new restaurants and galleries in the 1990s, Hartford has so far stubbornly resisted gentrification. That’s a shame, since its downtown is home to many fine attractions and magnificent architecture left over as a legacy of its one-time status as an important river shipping port.

Hartford was settled soon after Boston, when Thomas Hooker led an expedition of 130 souls to found a settlement just north of a Dutch trading port in 1637. For the next two hundred years it flourished as a port city, despite being more than 30 miles away from the nearest ocean. After trade declined in the mid-19th century, the city reinvented itself by selling insurance to protect ship’s cargoes; from that seed the city grew into the so-called “insurance capital of the world.”

Even today, it is headquarters to many insurance companies, such as Travelers, which keep it bustling during the week. On weekends, however, it’s a different story—and a different city—as white-collar workers go home to the suburbs and leave downtown a ghost town. Not that that means you should avoid the city at that time; the lack of crowds makes weekends the best time to check out its many museums and historic sights.