With New Haven as the big draw for visitors, the outlying areas of the city are generally content to serve as quiet suburbs. As the sixth-oldest town in the state (founded in 1639), the small but squeaky-clean Milford abuts a pretty harbor fed by Long Island Sound. The town green, complete with gardens, a gazebo, and several monuments, is the pride of the community.

Just north of New Haven, the cultural mecca of Hamden sits in the shadow of an unusually shaped mountain known as the “sleeping giant” for its similarity to a reclining man. In addition to acres of hiking and biking trails, the town was once home to inventor Eli Whitney.

Up the coast to the east, meanwhile, the pretty seaside towns of Brandon and Guilford compete in the beauty contest with their own meticulous town greens. Brandon is known for its quirky museums and revitalized downtown, as well as its ready access to the beautiful Thimble Islands. Guilford sports several historic house museums as well as miles of trails along picturesque coastal wetlands.