Wikipedia:
The Nipmuck Trail is a Blue-Blazed hiking trail "system" which meanders through 34.5 miles (55.5 km) of forests in northeast Connecticut. It is maintained by the Connecticut Forest and Park Association and is considered one of the Blue-Blazed hiking trails. There are two southern trail heads (two tines of a fork) in the south of the town of Mansfield, Connecticut. The southwestern terminus is at a road shoulder parking place on Puddin Lane, and the southeastern terminus is a DEEP parking lot on North Windham Road at the southeast corner of Mansfield Hollow State Park. The northern terminus is at the north end of Breakneck Pond along the Massachusetts border in Nipmuck State Forest. Camping permits may be obtained for up to five separate locations for backpacking.
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).[2][3][4]
The Nipmuck Trail Race covers only part of the complete trail.
Scott Livingston added more details:
The Nipmuck Trail extends from Mansfield north to the Massachusetts border. It is part of the 825-mile Connecticut Forest & Park Association (CFPA) Blue-Blazed Hiking Trail network. The trail is shaped roughly like an upside-down fork and has two southern branches: the West Branch starts on Puddin’ Lane in Mansfield; the East Branch starts in Mansfield Hollow State Park in North Windham. The northern terminus of the Nipmuck Trail is in Bigelow Hollow State Park.
The longer East Branch begins at the southern terminus trailhead in the North Windham Road parking lot at Mansfield Hollow State Park. The West Branch is maybe 2 miles shorter. The out & back should hit both branches.
The CFPA Walk Book lists the total distance using the East Branch as 36.3 miles. There is approximately 4,961 feet of elevation gain in the South to North direction.
The trail crosses through a number of recreation and conservation areas including Mansfield Hollow State Park, the Natchaug and Nipmuck State Forests, Schoolhouse Brook Park, the Yale Forest, Bigelow Hollow State Park, and other lands owned by towns and land conservation trusts, most notably Joshua’s Trust. Highlights on the trail include Mansfield Hollow Lake, 50’ Cliff, Pixie Falls, Ladies Room Rock, Coye Hill (highest point on the trail), and the Fenton and Mount Hope rivers. The mostly singletrack Nipmuck Trail crosses open field, follows along ridges and woods roads, and provides a continuous spine to which numerous other trail systems connect.
The northern terminus is in Bigelow Hollow State Park on the east shore of Breakneck Pond where the trail meets the Massachusetts border.
https://ctwoodlands.org/trails/nipmuck-trail/
Comments
Saturday 10/24 I attempted to establish a time on the Nipmuck Trail E2E2E from the SW terminus to the Mass Line and back to the SE terminus for an approximate distance of 68 miles. Â I started at 4:17 am and ran for about 3 hours in the dark and then reached the Mass line in about 7:40. Â On the return trip my pace slowed considerably, and I ended my run early at about 53 miles at the Route 74 crossing. Â I decided that it would be unsafe to navigate the leaf-covered rocks and roots in the dark for several hours while fatigued. Â I plan to return next year when there is more daylight and less leaves on the trail. Â I ran unsupported with 2 bottles and a BeFree filter and mostly had no trouble finding water. Â There is a fairly long section that was dry from Pixie Falls to Bigelow Hollow, but I anticipated this and managed the section. Â I can provide detailed instructions regarding water locations to anyone interested.