The northern terminus is at the north end of Breakneck Pond along the Massachusetts border in Nipmuck State Forest.

For 9 miles (14 km) the Nipmuck Trail travels through the Yale-Myers Forest which is owned by Yale University.

The trail also traverses 3.5 miles (5.6 km) of the University of Connecticut's East Campus (the protected Moss tract through the Fenton Forest).

For about 6 miles, the trail follows the Fenton River from the University of Connecticut to Mansfield Hollow State Park.

[2] Also on that date a number of conveyances between the University of Connecticut, CFPA, the Norcross Wildlife Foundation and the towns of Willington and Mansfield secured the preservation of 531 acres (2.15 km2) of land on four forested properties near or surrounding the Nipmuck Trail.