The Highlands Trail in Chester, NY: A Stroll Through Wilderness That Might Not Have Been

By Sona Mason, West Hudson Program Coordinator 

The Highlands Trail is finding new life in Chester, N.Y.

The Highlands Trail is finding new life in Chester, N.Y. (Photo credit: Sona Mason)

In Chester, N.Y., not far from the hamlet of Sugarloaf, the Highlands Trail (HT) has been given the chance to “get back to nature,” courtesy of a major conservation victory. On Christmas Eve, 2014, a 400-acre parcel that had been slated to become a 222-unit residential development was purchased by the Open Space Institute (OSI) to remain forever green. This acquisition, made possible by the Trail Conference and its partners, is an important step in creating an uninterrupted greenway connection between Goosepond Mountain State Park and Sterling Forest State Park. For the HT, that means a major portion of the trail is now rerouted off a busy roadway and onto beautiful woodlands.

Highlands Trail in Chester Map

You can view and download a map of the Highlands Trail through Goosepond South at

The Highlands Trail, blazed with teal diamonds, leaves its road walk from Sterling Forest along Lakes and Laroe roads, turns onto Bull Mill Road, and right into the forest, just past the bridge crossing over Trout Brook. A new kiosk and bench, compliments of OSI, welcome you to this part of the trail with a short history of the parcel’s acquisition and map of the trail and property. Since this property joins up with Goosepond Mountain State Park’s southern end, it’s been named Goosepond South by OSI, who hopes to hand it over to the New York State Parks system in a few years.

Access the trail via a gravel parking pullout located just after the crossing of Trout Brook on Bull Mill Road, about 1/4 mile from the intersection of Laroe Road in Chester. The easy first few hundred yards of the trail skirt the edge of an open wildflower field, along the edge of a line of stately sycamores and grand old sugar maples. The path turns at the bend of Trout Brook, which presents superb pebble-skimming opportunities. Steadily climbing uphill, the trail passes through a variety of ecosystems, including quiet red cedar groves, to a view sweeping west toward Sugarloaf Mountain. From there the trail heads downhill, crossing over Bull Mill Road, onto the northern part of the property. It travels across a rushing stream and hummocky wetland, ending uphill at a stone wall marking the boundary with Goosepond Mountain State Park.

Lovely scenery on the HT

Lovely scenery on the HT

Future plans will connect the HT with trails in this neighboring park. Until then, we have a new view and pleasant stroll over wilderness that might not have been, as Howie Cohen, neighbor and avid volunteer on the trail, remarked. “We shiver at the thought of what could have been if not for the like-minded people who know the power of the land’s natural beauty and helped preserve this land,” Cohen said. “My wife Vicki and I are so appreciative of the Trail Conference and OSI for investing their resources in our backyard.”

While the trail is open, there’s still work to be done on the reroute—and we could use your help! Volunteers are working on this project throughout the summer, including some Wednesday evenings; find planned work dates here. Anyone with an interest in contributing to the creation of a beautiful, sustainable new HT is welcome to help. No experience is necessary; we provide tools and training on-site before getting started. We’ll also be holding a special Trail University workshop on how to build a stream crossing on August 1. Please sign up for the free workshop so that we can bring enough tools. For more information about the HT reroute in Chester and volunteer opportunities on the trail, contact West Hudson Program Coordinator Sona Mason: or 201-512-9348 ext. 16.

About Trail Walker

Since 1920, the New York-New Jersey Trail Conference has partnered with parks to create, protect, and promote a network of more than 2,100 miles of public trails in the New York-New Jersey metropolitan region. The Trail Conference organizes volunteer service projects that keep these trails open, safe, and enjoyable for the public. We publish maps and books that guide public use of these trails. The Trail Conference is a volunteer-driven nonprofit organization with a membership of 10,000 individuals and 100 clubs with a combined membership of 100,000 active, outdoor-loving people.
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