September 10, 2025

Litchfield’s Revolutionary Roots in Autumn
By Lydia Kennedy

Photograph courtesy of Litchfield Historical Society

As the crisp autumn air rolls through the Litchfield Hills, there is no better time to take advantage of the region’s history, where the legacies of Revolutionary War figures are preserved in its classic Colonial structures and unforgettable landscapes. 

Begin in Litchfield, home to the nation’s first law school, founded by Tapping Reeve in 1784. This pioneering institution trained nearly 1,000 men, including Aaron Burr and John C. Calhoun. Reeve’s historic schoolhouse still stands, allowing visitors to journey through the 19th-century life of a real Litchfield Law student. 

Continue your adventure north toward the rugged terrain favored by Ethan Allen, a soldier and frontiersman who led the Green Mountain Boys during the American Revolution. Allen’s revolutionary spirit is reflected in the beauty of Connecticut’s western frontier, especially when hiking Bear Mountain or Mount Riga. 

Then there is Benjamin Tallmadge, Washington’s very own spymaster and a native son of Litchfield. As head of the Culper Spy Ring, a covert intelligence network, Tallmadge fed crucial information about British-occupied New York directly to General George Washington. Today, you can walk on the same Green where Tallmadge drilled his militia—and returned to after the war. His Federal-style home still stands just off North Street. 

Connecticut remains dotted with Colonial homes and worn stone walls, all telling stories that intertwine centuries of history with the enduring beauty of New England.