Bring the Trail to Life: A Day of Art & Fun in Windham, Maine

Windham, Maine is about to get a splash of color, and it’s all happening right in my neck of the woods!

Chalk the Trail kicks off on Saturday, May 18th, from 10:00 AM to 1:00 PM at Soccer Drive (Gambo Fields). This free, family-friendly celebration invites community members of all ages to come together for a day filled with artistic expression, local engagement, and springtime fun.

The main event is, of course, the chalk art. Participants are encouraged to use their imagination as they decorate the scenic trail with vibrant drawings, uplifting messages, and colorful designs. Chalk will be provided on-site, but guests are welcome to bring their own supplies to add a personal touch to the trail.

Alongside the artwork, attendees can enjoy food from Great Scott’s MacWagon, a popular food truck offering comfort food classics perfect for a day outdoors. The event also features giveaways and surprise goodies, adding an extra layer of excitement for both kids and adults.

Several local organizations will be on hand to share resources, engage with attendees, and offer interactive, hands-on activities. It’s a great opportunity to connect with neighbors, learn more about Windham's community programs, and simply enjoy a day outdoors.

Whether you're an artist at heart or just looking for a way to enjoy the spring weather, Chalk the Trail promises creativity, connection, and plenty of color. Mark your calendar and bring the whole family. Windham’s trail is waiting for your masterpiece!

Fingers crossed for good weather, but just in case, there's a rain date of May 25.