East Bayside Trail Fest
Back Cove, United States • 28 Jun 2026
East Bayside Trail Fest : Portland, ME
The East Bayside Trail Fest takes place on Sunday, June 28, 2026, in the East Bayside neighborhood of Portland, Maine. The event is a collaboration between Portland Trails and the Bicycle Coalition of Maine, presented by Kennebec Savings Bank. Activities culminate in a community celebration on Diamond Street featuring music, food trucks, and local beer and spirits. Proceeds support Portland Trails and the Bicycle Coalition of Maine.
Events and logistics
Distances offered:
- 10K Trail to Ale
- 15-mile Bayside Ride option
- 30-mile Bayside Ride option
- 2-mile Trail Mix
The Trail to Ale 10K is a timed road/trail race with age-group awards. The course offers views of Casco Bay, Back Cove, and Portland’s skyline. The Trail to Ale start is at 175 Anderson St and the finish at 34 Diamond St. Registration for this event includes a beverage at the post-race celebration; participants receive two free-drink tear-offs on their bibs.
The Bayside Ride is a non-competitive group bike ride with 15-mile and 30-mile route options that head north through Portland, Falmouth, Cumberland, and Yarmouth. Rest stops with refreshments are provided, e-bikes are allowed, and the ride is not timed. Participants receive two free-drink tear-offs for the after-party.
The Trail Mix Two-Miler is a family-friendly, untimed trail run/walk. Registration for this event is $15, with a discounted family rate for groups of four or more. Packet pickup is available at 38 Diamond Street (Portland Trails office) on the days before and the day of the event. Visit the organization's website for the most recent information.