Round Jeremy's Trail on any weekday morning, a 0.4-mile loop through Emmons Preserve, and you are walking the same ground Steve Emmons first cut a path through in the late 1990s, back when the woods were still his own and there was no trust, no headquarters, and no name for any of it. He donated the land not long after, and the path only became Jeremy's Trail later, renamed in memory of a fifteen-year-old named Jeremy Walker Georgitis. That gap between how settled a place feels underfoot and how recently it was actually cut, donated, or renamed is the real story of walking in Kennebunkport this year.
Most people who live here carry a mental map of the town's outdoor life that stops at the harbor loop and Ocean Avenue. That map is not wrong. It is just out of date. A meaningful share of the trail network residents rely on for a daily walk, a dog off leash, or a quiet hour away from Dock Square did not exist ten years ago, and one piece of it is still being built right now, on Mills Road, a few miles from where most people assume the town's green space ends.
A tiny staff behind a very large footprint
The organization that owns and maintains almost all of this is the Kennebunkport Conservation Trust, a nonprofit founded in 1973. Today the Trust stewards over 3,000 acres, twelve harbor islands, and 30 miles of trails, all run by four full-time and two part-time employees. That ratio matters more than it sounds like it should. A land trust that size, with that little paid staff, does not expand its trail system through press releases. It expands through donated parcels, volunteer labor, and a board that meets once a year to report on projects most residents never hear about until they stumble onto a new trailhead sign. That is exactly what has been happening at two properties most people drive past without a second look.
The map most people already know
Emmons Preserve, at 57 Gravelly Brook Road, is the Trust's headquarters and its oldest developed property, built on land donated by Steve and Natalie Emmons specifically so children could connect with nature. It is also the easiest place to see how the network actually grew, one named trail at a time.
| Trail | Length | What it's named for |
|---|---|---|
| Roller Trail | 1 mile loop | Longtime volunteers Mark and Gail Roller |
| Jeremy's Trail | 0.4 mile round trip | Jeremy Walker Georgitis, who died at fifteen |
| Batson River Trail | 1.8 miles | Runs from Trust headquarters to Tyler Brook Preserve |
| Learning Trail | 0.7 mile loop | Thirteen stations built with Kennebunk High School |
| Jenne's Loop | 0.5 mile | Connects to an overlook above the Batson |
The Community Labyrinth sits just off the Learning Trail, a stone-dust path accessible by wheelchair and stroller from the trailhead through the labyrinth itself. According to the Trust, the stones that form it were donated by community members, and it was "designed to be as accessible as possible." One of those stones was chosen by a group of Arab and Israeli young people who visited together through a program called Forever Friends, and it now sits marking the labyrinth's east axis. None of that is on a plaque you'd notice from the road.
The corner most residents haven't found yet
If Emmons Preserve is the network's oldest developed core, the James Trail is its newest addition inside the village itself, and it is still only six years old. It opened in the fall of 2020 on 15 wooded acres donated by David and Lisanne James, beginning on the east side of North Street barely 100 yards from the town parking lot. The mile-long route passes views of the tidal inlet at Mast Cove, winds through stands of ferns, and crosses a 24-foot ravine on an arched bridge built over a firebreak that was dug in 1947 to help stop that year's fires from spreading. Parking is at 30 North Street. A trail this close to downtown, carrying a piece of 1947 fire history in its bridge, is not something most longtime residents grew up walking, because for most of their time here it simply was not there.
The bigger shift is happening farther out, on Mills Road toward Biddeford, at a property called Meadow Woods Preserve. Its story did not start as a trail project at all. In 2006, Gloria and Eric Moline donated 19 acres there with no plan beyond conserving a landlocked parcel. It had no name until 2019, when a much larger gift from the Hutchins family, nearly 133 acres, turned it into something worth naming. Between 2018 and 2021 the Trust purchased close to 200 more acres to connect the pieces, and two sections that had previously been excavated for soil, about seven acres total, became the property's most-used amenities: a spring-fed pond the Trust calls Pollywog Pond, ringed with a stone table and benches, and a fenced, tree-lined off-leash dog park.
The preserve now has its own small network of named paths: the Forager Trail, a 0.15-mile connector to the pollinator meadows named for Patsy Bray Mahoney, the short stone-dust Tommy McNamara Trail from the parking area to the pond, and Patsy's Path, a 0.46-mile loop around the pond and meadows. According to the Trust's own 2024 annual meeting update, the work is not finished. The plan going forward calls for a second off-leash dog area and a small, four-season welcome and education center on the property.
"Especially excited about the new dog park at Meadow Woods Preserve."
That is how one longtime board member, a veterinarian who has practiced in Kennebunkport for 40 years, described his own reaction to the project in the Trust's staff bios. If a board member who has watched the organization for two decades is still catching up to what is being built, it is a fair bet most residents are too.
The fixed points that give the rest of it context
Not everything is new, and the older landmarks are worth knowing precisely because they anchor how much has changed around them. Goat Island Lighthouse, visible from the beach at Cape Porpoise Harbor, was established in 1833 and has marked that harbor mouth for nearly two centuries. Ganny's Garden, tucked onto the Trust's River Green in the heart of the village, was planted in the fall of 2011 as a surprise for Barbara Bush from friends and family, its layout inspired by a needlepoint carpet she made that hid her grandchildren's initials among the flowers. And the Trust's largest single holding, the Smith Preserve, carries over 1,100 acres and 10 miles of trails on its own, part of a 3,000-acre block of undeveloped land that is the largest contiguous piece between Kittery and Brunswick on the Maine coast. None of that is going anywhere. It is the newer corners of the map, concentrated at James Trail and Meadow Woods, that keep shifting under people's feet.
Where to actually go this month
If you want to see the gap between the old map and the current one for yourself, a short list of addresses covers most of it:
- Emmons Preserve and Trust headquarters: 57 Gravelly Brook Road, for the Roller Trail, Jeremy's Trail, and the Community Labyrinth
- James Trail: public parking at 30 North Street, trailhead just down the street and across the road
- Meadow Woods Preserve: 406 Mills Road, look for the large engraved rock at the entrance and the dirt driveway down to the pond and dog park
The Trust also holds the Grist Mill Property on Mill Lane, acquired in 2006, which gives walking access to Mast Cove, the site of the old Perkins Grist Mill, and the Clement Clark Boathouse, all within walking distance of the lower village for anyone who wants a shorter loop before dinner.
Why this matters if you already live here
None of this changes what Kennebunkport looks like from Dock Square. It changes what the town offers on a Tuesday evening after work, which is a different and, for most residents, more useful question. A trail system built almost entirely on private donations and volunteer hours does not announce itself the way a new restaurant does. It shows up as a rock at a trailhead, a fence line around a pond, a line on a map that was not there the last time you looked closely. The version of Kennebunkport most people carry in their heads is the one they learned when they moved in. The version on the ground right now has at least two pieces, one downtown and one out toward Biddeford, that are younger than a lot of the cars parked at the trailheads.
Whether you have lived near one of these trailheads for twenty years or you are simply curious what else the Trust has quietly built while you were not looking, it is worth a walk before the next annual meeting update changes the map again. I spend my time in these small, specific details of daily life here because they are usually the ones that matter most once you actually live somewhere. Shanna Jadooram is always glad to talk through what a corner of Kennebunkport offers beyond the listing photos. Let's Connect.
