East Bayside Trail Fest

Event Overview

The Kennebec Savings Bank East Bayside Trail Fest takes place in Portland, Maine, specifically in the East Bayside neighborhood. The event features three separate activities staggered throughout a Sunday morning.

The activities include:

• Trail to Ale 10K: A timed trail race presented by Martin's Point Health Care. It features views of Casco Bay, Back Cove, and the Portland skyline, with awards for top finishers and age group winners.
• Bayside Ride: A casual, non-competitive group bike ride hosted by the Bicycle Coalition of Maine. It offers 15-mile and 30-mile route options through Portland, Falmouth, Cumberland, and Yarmouth, with rest stops and refreshments. E-bikes are welcome.
• Trail Mix 2-Miler: A family-friendly, non-timed fun run and walk on the trails, also presented by Martin's Point Health Care. It welcomes all ages and skill levels, including people with strollers.

Following the activities, there is a community celebration with music, food trucks, and local beer.

Registration and Fees

Registration fees vary by event. The Trail to Ale 10K and Bayside Ride cost $50, though this price increases after February 28, 2026. Registration for these two events includes a complimentary event t-shirt and two drink tickets for the festival.

The Trail Mix 2-Miler costs $15. Registration for this event does not include a t-shirt or drink tickets. A discount of $2.50 per participant is offered when registering four or more people together.

Beneficiary

The event is the largest annual fundraiser for Portland Trails, a non-profit organization. All registration fees and donations support its work to maintain and connect a 100-mile trail network in the area. The event address is 38 Diamond Street, Portland, Maine. Visit the organization's website for the most recent information.