Chalk the Trail is a fun, creative, and family-friendly community event hosted by the Friends of the Mountain Division Trail. First launched in 2022, the event invites families, children, artists, and trail users to decorate sections of the Mountain Division Trail with colorful chalk art—transforming the trail into a temporary outdoor art gallery.
What began as a small community gathering has quickly grown into one of the most popular annual events celebrating the Mountain Division Trail. Each year, hundreds of participants come together to draw, create, and explore the trail while enjoying music, games, and outdoor activities. The event helps introduce new people to the trail and highlights the importance of preserving and expanding this important regional recreation corridor.
Chalk the Trail is designed to show that the Mountain Division Trail is more than just a place for walking or biking—it is also a place for community connection, creativity, and outdoor fun. Families spread out along the trail with buckets of chalk, creating colorful drawings, messages, and murals that brighten the pavement and bring the trail to life for everyone passing by.
Since its start in Fryeburg in 2022, Chalk the Trail has expanded to include multiple communities along the trail corridor, including Windham, helping more residents experience the trail firsthand. Each year the event continues to grow in participation and partnerships, with support from local organizations, volunteers, and community sponsors.
Beyond the artwork, Chalk the Trail also helps raise awareness about the ongoing effort to complete the full Mountain Division Trail from Portland to Fryeburg. By bringing people onto the trail in a fun and welcoming way, the event strengthens community support for building and improving this important recreational and transportation corridor.
Today, Chalk the Trail has become a beloved tradition that celebrates creativity, community, and the shared vision of a connected trail network across Southern and Western Maine.