Lace up for an unforgettable experience at the East Bayside Trail Fest on Sunday, June 28, 2026, in the vibrant East Bayside neighborhood of Portland, Maine. This distinctive event offers both the challenging Trail to Ale 10K and the family-friendly Trail Mix Two-Miler, catering to all running enthusiasts. The Trail to Ale 10K, a beloved local favorite making its return, winds through scenic trails and roads, providing breathtaking views of Casco Bay, Back Cove, and Portland's iconic skyline as it traverses the Back Cove Trail, Bayside Trail, and Payson Park. Approximately 50% of the 10K course is on unpaved trails, promising a true trail running adventure. For those seeking a more relaxed pace, the untimed Trail Mix Two-Miler is perfect for all ages and skill levels, even welcoming strollers for a fun-filled community walk or run on the trails.

What truly sets the East Bayside Trail Fest apart is its vibrant community atmosphere and its mission to support local trails. Starting points for the 10K are at the intersection of Cove St & Anderson St (or 175 Anderson St), while the 2-Miler kicks off on Diamond Street, with all races culminating in a lively block party on Diamond Street. Here, runners, spectators, and locals alike can enjoy live music, indulge in delicious offerings from food trucks, and sample local beer, cider, and spirits. Historically, runners have expressed excitement for this event's return, highlighting high energy and a great time on the course. Typical race day conditions in late June bring comfortable highs around 77F and lows near 59F, with only a 16% chance of precipitation, ensuring pleasant running weather.

Beyond the personal challenge and enjoyment, participating in the East Bayside Trail Fest contributes directly to the vital work of Portland Trails and the Bicycle Coalition of Maine. This collaboration between local nonprofits and businesses not only celebrates active living but also champions community engagement and neighborhood revitalization. As Portland Trails' largest fundraising event, your registration for the 10K even includes two complimentary post-race drinks to toast your accomplishment at the festive celebration. Join us for the second annual East Bayside Trail Fest for an unforgettable blend of scenic running, community spirit, and post-race celebration.