Cannondale Historic District

The Cannondale Historic District is a historic district in Wilton, Connecticut, spanning roughly 202 acres with approximately 58 historic structures along Danbury Road and near the Cannondale train station. The northern section called Cannon Crossing features restored 19th-century buildings that now serve as a shopping development.

The district contains structures dating from the early national period through the early 20th century, documenting agricultural and commercial activities of past generations. The Wakeman house features an underground tunnel with a trap door, which was used to transport individuals during the Underground Railroad era.

The buildings showcase Greek Revival, Victorian, and Colonial Revival styles that reflect how construction preferences evolved across generations in this region.

The best way to explore the district is by walking along Danbury Road and through Cannon Crossing, where most restored buildings are accessible. The area is straightforward to navigate and many shops and restaurants occupy the historic structures.

The district was a hotspot for illegal stills during Prohibition, with operators hiding liquor in hidden tunnel networks beneath the buildings. Historians continue to find evidence of this clandestine period in the area's records and structures.

Location: Connecticut

GPS coordinates: 41.22250,-73.42611

Latest update: December 14, 2025 13:03