"How much of this are we going to continue to buy?"
— Adam Dews, quoted in the Press Herald.
At the 2017 Town Council meeting, after members voted to add another piece to Knight's Pond Preserve, the lifelong Cumberland resident spoke. He wasn't objecting. He rattled off the town's recent acquisitions as he asked it: Broad Cove Reserve, Rines Forest, Twin Brook Recreation Area, the Town Forest. It read like a checklist of separate parks, each one nice on its own, each one a little more town money spent on land.
Nine years later, that's the wrong way to see it. The land the Chebeague & Cumberland Land Trust has spent almost four decades buying and easing doesn't sit in separate boxes. Pieces of it touch other pieces. The connected preserves offer a much larger landscape than any one trailhead suggests.
A Connected Trail Network
Start at Knight's Pond Preserve, off Greely Road Extension. At 163 acres it's the largest undeveloped parcel left in Cumberland, built around a 46-acre pond, a ridgeline running to roughly 500 feet, and views out to Casco Bay and, on a clear day, Mount Washington. The preserve continues beyond its own boundary: it abuts another 50 acres in North Yarmouth that the neighboring town and the Royal River Conservation Trust conserved separately, so a walker can cross a town line without noticing.
Go the other direction from Knight's Pond and there's a second connection, quieter and less obvious because it runs through a parcel most residents have never heard of. Farwell Forest is a 45-acre tract that exists almost entirely to link two bigger pieces together: it connects Knight's Pond Preserve to Rines Forest. Rines Forest itself isn't small. In late 2019 the land trust added a 52-acre parcel next to it that pushed the town-owned tract past 260 acres, and its own trail network continues on into Hadlock Forest across the line in Falmouth.
Knight's Pond, Farwell Forest, and Rines Forest together form more than 460 contiguous acres, with an open connection into North Yarmouth on one end and a trail continuing into Falmouth on the other. None of it requires a car to move between. None of it shows up as one name on a map, because it isn't one preserve. It's three, stitched together on purpose.
The Piece Everyone Actually Knows
Twin Brook Recreation Area is the exception, and it's the exception precisely because it's the one most people can name. It's town-owned rather than trust-owned, just over 224 acres, with about 4 miles of wooded walking trails plus 22 acres of ballfields, soccer fields, and a disc golf course. It has two entrances, one off Tuttle Road and one off Greely Road, and in winter the town grooms it for cross-country skiing. It's the park with the parking lots big enough for tournament traffic and the paved quarter-mile loop that's wheelchair accessible.
Twin Brook is Cumberland's front door to green space. It isn't part of the Knight's Pond to Rines Forest chain. That distinction matters if you're trying to understand how the town's conserved land actually functions: one system is built for volume, athletic fields, dog walkers on a Tuesday evening, disc golf leagues. The other is built for distance, a network of easements and donated parcels that keeps extending outward with less fanfare and no ballfields at all.
The Newer Additions Round Out the Map
The land trust hasn't stopped adding pieces since Dews asked his question. Closer to the town center, the trust accepted a 40-acre conservation easement for Greely Woods in October of that same push, a trail network across three adjoining undeveloped town-owned parcels bordered by Greely Road Extension and Sparhawk Lane, close enough to Main Street that it functions as a lunch-break walk rather than a destination hike.
Across both Cumberland and Chebeague Island, the trust now holds more than 1,200 acres conserved since it formed in 1987, under executive director Penny Asherman and board president Rod Vogel. That's roughly 30 separate properties, some connected into the Knight's Pond chain, some standing alone like Greely Woods, all of it added parcel by parcel by a volunteer-run nonprofit rather than delivered as one master-planned park.
Water Access Is Its Own Category
Broad Cove Reserve doesn't connect to any of the inland chain, and it doesn't need to. It's off Route 88 near Tuttle Road, and it exists because Cumberland voters approved a referendum in November 2014 to buy 12 acres of shorefront, including the beach and pier, plus 9 more acres along Route 88 to connect them. It's the only piece in this whole network with direct saltwater access, and the town calls it the best waterfront public access it has.
The rules there are different from the inland preserves in a way that trips people up. Dogs are prohibited on the beach itself but permitted on the trails, leashed. Bikes and motorized vehicles are barred entirely. A sign on the property notes the land's earlier use as Abenaki fishing grounds and later as the town farm, a detail that predates every trail marker on it.
What This Means for a Fall Weekend
None of this is abstract if you're deciding where to spend a Saturday between now and Halloween. The Knight's Pond ridge is the best foliage view in the network because it's the only piece with real elevation, and the trails along Blueberry Hill pass through oak and hickory forest that's genuinely uncommon this far north in Maine. Rines Forest is the better choice if you want tree cover the whole way rather than open ridge. Twin Brook is still the right call if you're bringing kids who need a ballfield to run around afterward, or a dog that does better off-leash on the Greely Road side than on-leash at Tuttle Road, since the town's rules differ by section.
The Fair Still Anchors the Calendar
Cumberland's oldest use of open land isn't conservation at all. The 154th Cumberland Fair runs September 27 through October 3, 2026, on Blanchard Road, with the pumpkin contest and squash weigh-off that have been fixtures for generations and an All American Rodeo running Wednesday and Thursday evenings. It's the same town, using land two completely different ways: one plot given over every fall to livestock barns and midway rides, the rest of it quietly extended, easement by easement, into trail.
Dews got his answer, just not in a council meeting. The trust kept buying, past 1,200 acres now, and the payoff wasn't more disconnected parkland. It was a network a person can actually walk end to end, from a ridge with a view of Casco Bay to a trail that crosses into Falmouth, without a single mile of it requiring a car.
If you already live here, you probably know one piece of this well. Worth finding out how far the rest of it actually goes before the leaves are down.
If you're weighing a move to Cumberland, or thinking about what a place like this is actually worth to live near, Ashley Fearon and the team at A Team Realty know this town's trails as well as its listings. Book your free seller strategy consultation and let's talk about what's next.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
