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The most accessible trailhead for the Upper Lake Loop is near the entrance to the Kendall Sports & Dance Complex and the dam and waterfall on Upper Lake, just after crossing Park Street. The loop is approximately one mile long and primarily circles the entire lake. The loop will take you past the lake and its bordering wetlands and some stands of upland hardwood forest. Wetlands along the lake border include marsh, scrubby wetlands, and some small stands of forested wetlands. The loop will also take you past the Restoration Ecology Program’s wetland restoration project, identifiable by the boardwalk and information kiosk. In addition, a vernal pool borders the trail just above MacGregor Hall.

The Stony Brook Trail is also accessible from the Upper Lake Loop.

Two trails run parallel to the eastern side of Stony Brook, forming a loop. These trails can be entered from several locations off of the Upper Lake Loop, but the most accessible trailhead is at the far end of the Upper Lake loop, near the bridge by the path up to the Equestrian Center. Taking the trail closest to Stony Brook will start you on the Stony Brook trail, which takes you 1.6km along the stream until you reach the cross-country field at the Long Farm. Make a left and walk up the field until you see a trail on your left marked by a sign dedicating the field to the Equestrian Center. This marks the beginning of the Long Farm trail. Follow this trail 1.6km through the woods and back to the trailhead, completing the loop.

There are several trails winding through the forest covering Prospect Hill. These trails traverse through some mature hardwood forest, mixed conifer and hardwood forest, and hemlock stands.

Carriage Way Loop

The main Carriage Way Trail can be entered at the sign by the guardrail behind Prospect Hall. This path winds up the hill in front of a hemlock and pine stand and then curves around where the trail diverges. At the point where the trail sharply turns, bear left and continue ascending Prospect Hill. You will shortly encounter another split in the trail. This marks the beginning of the loop around Prospect Hill, and you can go either way. This main loop will take you to the crest of Prospect Hill, though some grassy/herbaceous openings, and past one of the two town water supply tanks. On either side of the water tank are areas of blowdown (trees toppled during windstorm.) The loop also curves around the field above the Ham/MacGregor parking lot and then goes back into the woods. On the western side of the loop, near the opening for the Ham/MacGregor parking lot, the trail intersects with the 1882 footpath -- stay straight here to remain on the Carriage Way Loop. After completing the loop, head back down to the trailhead.

1882 Footpath

The trail is accessible from the Prospect Hall parking lot, beneath the Willits Hallowell center and is marked with a sign. The 1882 Footpath was recently named so after historic maps of campus showed a trail opening near the current Prospect Hall parking lot. The trailhead was located, but the trail itself was found overgrown and hard to follow. Facilities (with the help of several staff members) cleared the trail, opening it to hikers, and now the trail takes visitors through a jaunt of the upper section of Prospect Hill, intersecting with the Carriage Way Trail.

Begin this trail at the trailhead and ascend Prospect Hill following a number of switchbacks. The trail will intersect with the Carriage Way trail, but stay straight and follow the switchbacks until you reach the Prospect Hill weather station. The trail culminates at this weather station, and to the right of the weather station, you will see the remains of the foundation of the old pavilion at the top of the hill. This trail does not make a loop, so you will either need to follow the trail back down to the trailhead, or join the Carriage Way Loop and follow the instructions in the section above.