There are innumerable hiking trails in the watershed’s high hills, including three major long-distance trails.

The Appalachian Trail, the 2,000-mile footpath from Georgia to Maine, runs through much of the eastern portion of the watershed, climbing up and down in the Hoosac Range and the Green Mountains. (The Long Trail, which runs through Vermont from Massachusetts to Canada, shares the route of the AT in this section.) The trails cross MA Rt. 8 in Cheshire, MA Rt. 2 in North Adams, and VT Rt. 9 in Woodford. Several trail shelters along the way make a walk through the watershed on the AT/LT a comfortable two- to four-day backpack. Streams and ponds are plentiful. Views are extraordinary, especially from Mt. Greylock, Pine Cobble, and Harwood Hill. The recently restored Glastenbury Mountain fire tower is just beyond the watershed divide on the northeast.

The Taconic Crest Trail begins off Madden Road in Hancock, MA and ends on NY Rt. 436 in Petersburg, NY. The mostly ridge-line trail traverses a total distance of about 29 miles, with an “up” of 7,827 feet and a “down” of 9,470 feet. A trail beginning in Hopkins Forest, a Williams College research facility west of Williamstown, and a trail beginning on Prosser Hollow Rd. in Petersburg provide alternative access to the ridge. Other alternative access paths begin in the Berlin (NY) State Forest, and Mattison Hollow Road off NY Rt. 22 in Cherry Plain.

Special features of the trail include an old ski area, great views from the high points near Rt. 2, and something called the “snow hole” – a very cool, mossy cleft that, it is said, has held snow even in August. The Taconic Hiking Club sponsors an End-to-End hike along the trail every two even-numbered years. Early pre-registration is required and the number of hikers is limited.

Shorter hiking possibilities are present in a number of federal, state, municipal, or private open spaces.

The Mt. Greylock State Reservation contains many miles of trails. Favorites include Bellows Pipe Trail, Hopper Trail, and Money Brook Trail.

In the Green Mountain National Forest, the trail to the Dome in Pownal, the trails around Woodford Lake in Woodford State Park, and the trail to White Rocks on Bald Mtn. in Bennington are popular.

The Mile-around Woods, owned by the Fund for North Bennington, sits adjacent to the historic Park McCullough House in North Bennington, VT. The site is renowned for its spring wildflowers.

In New York state, Mt. Tom State Forest in White Creek offers extraordinary views southward to Mt. Greylock, unusually rich assemblages of spring wildflowers and ferns, and painfully large historic stone walls. Right on the watershed divide, in the Batten Kill State Forest in Jackson, Peaked Rock provides views north to the Adirondacks.

Tibbets State Forest in the Town of Hoosick permits ATV use by handicapped riders with a permit. Large trees and an ancient road are highlights on this property.