During the late 1700s, the small village of Cherry Valley was the gateway to America's Western Frontier. Located along a well-traversed Indian path, the geography surrounding the village made it perfect for western migration on the Cherry Valley Turnpike – now known as Route 20, a NYS Scenic Byway. After the Erie Canal opened in 1825, the village was less-traveled; but the advent of post-WWII auto travel breathed new life to the tiny village.

"Tiny" in size only, Cherry Valley became an artist haven during the 1960s and 70s, a place where Allen Ginsberg and other beatnik-types called home.

The architecture is notable, with the oldest bank building west of Albany still in use. The Cherry Valley Museum documents the history of the area; the Plaid Palette offers some of the finest Irish merchandise in upstate New York; and visitors can experience fine dining, superb lodging and shopping treasure hunts.

Cherry Valley Artworks continues the tradition of avant-garde arts-related activities, including renovating an old theater for upcoming performing arts, as well as a not-to-be-missed semi-annual Kite Festival.

Just down the road, visitors can discover the Old Middlefield Schoolhouse Museum and explore outdoor recreation at the Roseboom State Forest.