The New Haven & Northampton Canal Rail Trail closely follows the path of what was once the New Haven & Northampton Canal, a man-made waterway that served as a freight transport passage between New Haven, Connecticut and Northampton between 1835 and 1847. During its time, the canal was the most efficient option for overland transportation, as movement on the fluid, level surface made travel by canal smoother, faster and less expensive than travel on contemporary roads. The success of the canal was short lived, however, as just after a decade of use, portions of the canal were filled in those portions became part of the New Haven and Northampton railroad. Some canal landscape features still exist along the path of the rail trail.

The Northampton section extends from the MassCentral Rail Trail to the Easthampton Town Line, with the trail currently extending through Easthampton and eventually planned to connect to other rail trail sections to eventually create a continuous trail all the way to New Haven. In addition, the trail connects to the Hospital Hill Rail Trail Spur which leads to the former Northampton State Hospital, now known as Village Hill.

The New Haven and Northampton Canal Rail Trail is within walking distance for 50% of the Northampton community and offers connecting points to the nearby cities of Easthampton, Hadley and Amherst.

One of the highlights of the trail is as it goes through downtown Northampton on a raised section, crossing a rail trail bridge over Main Street with a trail related art mural on the bridge.