The Paugussett Trail extends from its southern terminus at Buddington Road in Shelton, and travels north through the Shelton Lakes Greenway, Indian Well State Park, and Birchbank Mountain Open Space, then enters the Town of Monroe at Webb Mountain Park, and turns southwest to follow the Boys Halfway River.

Site-specific activities enjoyed along the route include hunting (very limited), fishing, horseback riding, bouldering and rock climbing (access).

The main trail then begins following the riverbank, passing a white-blazed access trail leading up from the Indian Well beach, and continuing for about two miles through sometimes difficult terrain before reaching another overlook of the Housatonic River at the Birchbank Mountain Open Space.

The trail then descends gradually, passing over an old charcoal mound and crossing Upper White Hills Brook at the side of the former Monroe Rod and Gun Club, where a chimney stands.

After another brief road walk on Thoreau Drive, the trail drops steeply to Round Hill Brook, which marks the Shelton/Monroe border and the beginning of Webb Mountain Park.

[4] Indian Well in Shelton is named the pool beneath the waterfall at the entrance to the state park as well as for the legend of a Native American tragic romance between a Paugussett brave and a Pootatuck maiden.

Note that only cars with Town of Stratford resident stickers are officially allowed parking privileges inside Roosevelt Forest (others are supposed to pay a non-resident fee though this may not be enforced).

[9] Paugussett is the name of an Algonquian-speaking[10] native American tribe and sachemdom existing in southwestern Connecticut in the 17th century.

Lake Zoar was created in 1919 by the construction of the Stevenson Dam to produce hydro-electric power and to provide Housatonic River vehicle crossing.

[14] Webb Mountain Park was a farm owned by the Mr. and Mrs. Alfred E. Wagner which was purchased by the Town of Monroe in 1972.

It is regularly maintained, and is considered easy hiking, with very few sections of rugged and moderately difficult hiking (notably the initial steep climb near the Indian Well waterfall and the steep climb using "stairs" between two suburban houses at Princess Wenonah Drive in Shelton).

Ice can form on exposed ledges and summits, making hiking dangerous without special equipment.

[17] Extensive flooding in ponds, puddles and streams may occur in the late winter or early spring, overflowing into the trail and causing very muddy conditions.

Some parts of the trail follow forest roads which often contain ruts from ATVs and four-wheel drive vehicles.