City: Canaan, CT

Category: Tours & Attractions

Telephone: (860) 824-0850

Address: 1 Railroad St.

Description: Part of the Housatonic and Connecticut Western Railroad systems in the 19th century, Canaan’s Union Depot was the oldest operating station in the US until it was devastated by fire in 2001. Today it is being renovated, and at the famous Canaan Railroad Days you can honor the tradition while having some good family fun. Every business in town and the larger area participates in this weeklong festival, which includes car shows, craft fairs, a treasure hunt, gold panning, a parade, and fireworks. And, of course, you can ride the old trains up to Great Barrington, Massachusetts (and back if you like). Check the schedule for the days (usually in July); this is a great time to visit northwest Connecticut.