The New England Trail flows through Holyoke down the backbone of Mount Tom Range and East Mountain. Through the Mount Tom Reservation it supports many side trails on the eastern flanks of Mount Nonotuck and Mount Tom.
As it leaves the Mount Tom Reservation, the trail still has side trails into the former Mount Tom Ski Area and then into the Whiting Street Reservoir area. As a hiker crosses Route 141, the trail enters East Mountain. To the east are side trails into the Holyoke Community College area and the Jarvis Road area and to the west are side trails to Mountain Road. Lastly, at the southern end of the trail in Holyoke, a hiker will have side trails to McLean Reservoir and Ashley Reservoir.