Falmouth and Cumberland land trusts to celebrate trail connection
Two Land Trusts Unite for Second Annual Trail Fest to Celebrate New Hampshire-Maine Border Trail Network
Cumberland — When the Falmouth Land Trust and the Chebeague and Cumberland Land Trust first joined forces to pursue a shared grant through Maine's new Trails Program, organizers knew the partnership meant something bigger than a single funding application. This year, that collaboration takes center stage at the second annual Trail Fest, a community celebration and fundraiser set for Sunday, Sept. 27, at Wander at LongWoods Preserve in Cumberland.
The event, running from 3 to 7 p.m., promises a full afternoon of outdoor fun. Attendees can enjoy pizza and salad, visit a bar, listen to live bluegrass music, and explore guided trail tours of the surrounding conserved land. Family-friendly games and activities will keep younger visitors entertained, and a mountain bike raffle will offer attendees a chance to score a prized piece of cycling gear. Admission is $50 for adults and $5 for children ages 5 and older.
But beneath the festivities lies a serious mission. Trail Fest serves as both a tribute to the growing trail network linking Cumberland and Falmouth and a vital fundraiser. Money raised at the event will be divided evenly between the two land trusts and directed toward the ongoing maintenance and safety of their conserved properties.
"It takes a lot to manage the trails and keep them nice and usable and safe for everybody," said Penny Asherman, executive director of the Chebeague and Cumberland Land Trust. "So help us take care of them by supporting us, by coming to the event."
The seeds of the event were planted last year when the two trusts collaborated on a joint proposal to the Maine Trails Program, a $30 million bond approved by state voters in 2024. Their application focused on building and repairing trails that span the border between the two communities, broadening the trail network for residents in both towns. The application was successful, and work is now well underway.
Current projects include trail repairs at Hadlock Community Forest in Falmouth, an expansion of the parking area at Blackstrap Hill Preserve in Falmouth, and the construction of two miles of new trails at Watson Woods in Cumberland — a property the Chebeague and Cumberland Land Trust acquired last year. Together, these efforts represent a meaningful expansion of accessible outdoor space for the region.
Mila Plavsic, executive director of the Falmouth Land Trust, described the collaborative process as a series of fortunate overlaps. "There were a lot of threads that came together last year," she said.
Last year's inaugural Trail Fest drew more than 400 attendees, a turnout that underscored the community's enthusiasm for shared outdoor spaces. Organizers said the gathering also serves a more personal purpose: bringing together people who care about the land.
"Part of the event is a celebration, just coming together and … enjoying each other's company, other people who like to get outside," Plavsic said.
With small staff overseeing extensive tracts of conserved land, the two trusts rely heavily on community support to keep trails open and in good condition. Trail Fest has quickly become a cornerstone of that effort — a place where neighbors can connect over a shared love of the outdoors while contributing to the long-term health of the trails they use.
Those interested in attending can find more information through the Falmouth Land Trust at falmouthlandtrust.org or the Chebeague and Cumberland Land Trust at ccltmaine.org.
