Start at the small stone marker on Northwest Road, a quarter mile south of Alewife Brook Road, and you're standing on what used to be the front step of a schoolhouse that hasn't existed in over a century. Most people who walk the Grace Estate loop from here treat it as a straight shot to the water: into the pines, past Grassy Hollow, out to a view of Northwest Harbor with Cedar Point Lighthouse and Shelter Island across the channel. That's a real walk, and a good one. It's also the smallest piece of a trail system that actually connects three separate preserves under three different owners, and the seams between them are where the neighborhood gets interesting.
Grace Estate Preserve, the piece most Northwest Woods residents know best, runs over 500 acres of water and woods under Town of East Hampton ownership, with trails maintained for hiking, bird watching, and photography along the Northwest Harbor shoreline. Keep walking east past the harbor and you cross into different jurisdiction entirely: the Linda Gronlund Memorial Nature Preserve at Barcelona Neck, a state-owned tract named for a Sag Harbor native who was aboard the flight that went down in Pennsylvania on September 11. Barcelona Neck carries seven miles of trail, some dating back to the 1700s, climbing to 80-foot bluffs with panoramic views over Northwest Harbor and Sag Harbor Bay. Keep going past that and you're in Cedar Point County Park, Suffolk County land, where Alewife Pond connects to the harbor by way of the meandering Alewife Brook.
Three preserves, three agencies, one continuous shoreline. On a map it reads as a single green corridor. On the ground, each section gets maintained on its own schedule, by its own staff or volunteers, with its own blazing conventions. That's the part a first-time walker doesn't see coming.
The historical layer here is easy to miss unless someone points it out. Before Grace Estate was a preserve, it was a farming community. The 19th-century Van Scoy homestead, its family cemetery, and the schoolhouse site sit inside the woods you're walking through, and East Hampton Trails Preservation Society hikes routinely start right at the schoolhouse plaque. The community didn't survive the late 1800s. Farmsteads near the harbor were abandoned as the Northwest hamlet fell apart, leaving behind a scatter of foundations, graves, and place names that outlasted the households attached to them. Kirk's Place, on the shore of Northwest Harbor, and the former home site of Wickham Cuffee, one of the last Indigenous residents of the area, are both stops on the historic hikes that trace this ground.
The reason any of this existed here at all traces to the harbor itself. Northwest Harbor was East Hampton's main port from 1654 until the first wharf went up in Sag Harbor in 1761. For more than a century, this stretch of water was the town's connection to the outside world, which is why a working community grew up around it long before it became a place people go to look at scenery.
The connector between Grace Estate and Barcelona Neck is where the system shows its age. One detailed account of walking the DEC Barcelona loop describes a southern section of trail that's rarely used, with vegetation closing in on the tread, and blue disc blazes that have popped off the trees entirely in places, forcing the hiker to navigate by dead reckoning around the edge of the Sag Harbor Golf Course to pick the route back up. The same account describes wading through bog in the wetland crossing, finding planks in some spots and sinking mud in others, before the trail resolves again into open pinewoods along Northwest Creek.
None of that makes the connector unwalkable. It makes it a route that rewards someone who's done it before, or who's walking it with someone who has. That's precisely the gap East Hampton Trails Preservation Society exists to close. The group runs weekly Tuesday morning maintenance hikes specifically to keep as much of this trail network clear and blazed as volunteer labor allows, and new volunteers are welcome to show up with a lopper or hand saw. It's routine, unglamorous work, and it's the reason the well-traveled sections stay legible while the connectors lag behind.
The society's early-September schedule put two hikes directly on this ground. On September 19, the Grace Estate Historic Hike covered five miles through Grassy Hollow and the Grace Estate, stopping at the Van Scoy graveyard and Kirk's Place, led by longtime organizer Rick Whalen out of the Northwest Schoolhouse plaque on Northwest Road. Four days later, a shorter 1.5-mile walk focused on alewives, the fish that breed in Northwest's fresh water, met at the same schoolhouse plaque.
Those two hikes are useful less as an invitation and more as a pattern. Back in late June, the society ran a full weekend built around this same corridor: a three-mile Grace Estate Preserve loop walk led by Dave Luce, a 25-mile bike ride starting from Cedar Point County Park led by Carol and Bill Snee, and a Sunday paddle from the end of Alewife Brook Road out toward Cedar Point. Hiking, biking, and paddling all converge on the same few miles of shoreline because the terrain and the water access make it work that way, not because any one group owns the territory. The September dates just repeat the same logic on foot.
A few specifics worth having on hand year-round:
The instinct is to treat Grace Estate, Barcelona Neck, and Cedar Point as three separate outings, each with its own parking lot and its own afternoon. They're really one shoreline that a working port, a farming hamlet, and three different government agencies have each left their mark on, and the only entity actively stitching the seams back together is a volunteer trail society running a hike schedule that changes month to month. Walk the connector once with a group that knows where the blazes disappear, and the rest of the network stops feeling like three separate destinations.
For more on the ground Northwest Woods residents already walk, and the water it opens onto, The Burns Team keeps tabs on what's changing here month to month.
Compass
63 Main Street
East Hampton, NY 11937
Burns Team