Friday, May 15, 2026

Chalk the Trail brings color to Windham with art, family fun, and community connection

By Masha Yurkevich

Families, artists and outdoor enthusiasts are encouraged to gather in Windham on Sunday, May 17, for the annual Chalk the Trail event, a growing community tradition that transforms the Mountain Division Trail into a colorful outdoor art display.

Friends of the Mountain Division Trail and Windham Parks
and Recreation are hosting the annual 'Chalk the Trail' event
for the public on Sunday, May 17 to decorate the trail with
chalk art while learning more about the recreational trail
system. The family event runs from 10 a.m. to 1 p.m. at the 
Gambo Soccer Fields in Windham. COURTESY PHOTO  
The free event is hosted by the Friends of the Mountain Division Trail and Windham Parks and Recreation and invites participants of all ages to decorate the trail with chalk art while learning more about the popular recreational trail system.

“Chalk the Trail was my idea in 2022, the idea stemmed from wanting a trail event that was easy to put on, low cost, and family friendly,” says Andrew Walton, Secretary for Friends of the Mountain Division Trail. “I came up with the idea and started it in Fryeburg. After two years of doing it there and seeing it be successful, I added a twin event in Windham. Windham is our busiest section of trail, with over 344 users per day last year. We will get updated numbers this year but expect the number to rise.”

The Mountain Division Trail itself has become an important recreational resource for residents across southern Maine. The trail is used year-round by walkers, runners, cyclists and families looking for a safe outdoor space to exercise and enjoy nature.

Because the trail connects multiple communities, events like Chalk the Trail help introduce new visitors to the area while encouraging residents to spend more time outdoors.

The Chalk the Trail event brings trail users to the trail for a very different reason than to walk or bike and is a great way to connect with community members and share their love for the trail.

Unlike many outdoor recreation events focused on athletics or competition, Chalk the Trail encourages creativity and community engagement. Participants use sidewalk chalk to create drawings, messages and artwork directly on the pavement while visitors walk or bike through the trail to admire the displays.

“Friends of the Mountain Division Trail educate event participants on the progress of the trail expansion and for those who are on the trail for the first time, we tell them where it goes and what amenities are along the way. Last year we saw well over 100 people participate in Fryeburg and Windham,” says Walton.

The event continues to grow along with the popularity of the trail, he said.

“Chalk the Trail is our main event; it is needed to bring the community together on the trail and educate them on everything Mountain Division Trail,” Walton says.

The event has changed slightly over the years by moving the start time to a later hour to allow more people to attend. Since its inception, the number of participants has doubled, and this is the fourth year for the Windham Chalk the Trail.

Friends of the Mountain Division Trail and Windham Parks and Recreation Department are the main hosts of Chalk the Trail.

“Parks and Rec do a fantastic job assisting with parking and planning the event,” says Walton. “They are present at the event as well. Community tables are also there, and one that has been gaining popularity is the Lake's Region Kids Calendar.”

The Kids Calendar is a great resource for families to find events and tips on things to do.

“This year, we are trying a drawing contest where the participants will be judged and awarded prizes,” says Walton. “Otherwise, our goal continues to be the same: to educate and have fun chalking. We want this to be a fun event that was easy to bring kids to and learn about the trail.” 


Chalk the Trail in Windham will run from 10 a.m. to 1 p.m. Sunday, May 17 at the Gambo Soccer Fields connected to the Mountain Division Trail. Visitors should expect free chalk, temporary tattoos, giveaways, and many walk or bike the trail while at the event. All are encouraged to come and enjoy a fun event that is free and show their creativity.

To enter the Chalk the Trail Drawing Contest, please sign up at: https://forms.gle/BtFzL7YWFcNbJSNE8.

Another Chalk the Trail event will be held from 9 to 11 a.m. Sunday, June 21 at the Fryeburg Visitor Center on Route 302. <

No comments:

Post a Comment