Litchfield was settled in 1721, and looks very much the part of the quaint colonial town. It still boasts the 18th-century architecture of its beginnings, and the town center’s green is more pristine than ever. Surrounding it are streets full of tony and stylish boutiques and restaurants, which then lead out to wide avenues lined with historic homes.

Despite its remoteness, Litchfield played a big part during the Revolutionary War era, since it was a hotbed of Revolutionary sentiment that sired many famous figures from the age, including Vermont’s militia captain Ethan Allen, future vice president Aaron Burr, and several signers of the Declaration of Independence.

Because of that tradition—not to mention its almost impregnable position deep in the hills—Litchfield served as a command center and storehouse during the war. General George Washington passed through four times during 1780 and 1781, and Litchfield and its surrounding communities have painstakingly marked his steps and noted every place he laid his head at night.

A few miles away, Torrington, the largest city in Litchfield County, has been the industrial and commercial hub of northwestern Connecticut for more than a century now. Fringing its center are picturesque hills and valleys, while in its downtown area sits a sizeable stable of art deco architecture, an area deemed a national historic district in 1988. Despite the fine architecture, however, Torrington is now mainly a working-class city routinely overshadowed by its much cuter neighbors.