June 28th, 2026 | Portland, ME
LEARN MORE & REGISTER WITH PORTLAND TRAILS: Kennebec Savings Bank East Bayside Trail Fest – Portland Trails
Join the Bicycle Coalition of Maine and Portland Trails for their 2nd annual Kennebec Savings Bank East Bayside Trail Fest on June 28th! All registration fees and donations from the Kennebec Savings Bank East Bayside Trail Fest will support the work of two local nonprofits, Portland Trails and the Bicycle Coalition of Maine. Portland Trails creates connections between neighbors, communities, and the natural world through a 100-mile trail network. The Bicycle Coalition of Maine makes Maine a better and safer place to bike, walk, and roll. This is Portland Trails’ largest fundraising event of the year! There are three ways you can participate:
- Run the Trail to Ale 10K
- Bike the Bayside Ride
- Walk the Trail Mix 2-Miler
Once you cross the finish line, celebrate at a festival featuring music, food trucks, local beer, and more!
Event Information
Route Options
Join hundreds of other runners for this trail race with views of Casco Bay, Back Cove, and Portland’s iconic skyline. This race is timed and will feature awards for top finishers and age group winners.
Registration for the Trail to Ale 10K includes:
- One complimentary event t-shirt
- Two drink tickets for the festival
- Discounts to participating local businesses
Bayside Ride
This casual, non-competitive group bike ride is hosted by the Bicycle Coalition of Maine and features scenic views of Casco Bay. With 15-mile and 30-mile route options, the ride will head north through the towns of Portland, Falmouth, Cumberland, and Yarmouth. Rest stops will be positioned along the way with refreshments. Cyclists of all skill levels are welcome to participate! E-bikes are welcome.
Registration for the Bayside Ride includes:
- One complimentary event t-shirt
- Two drink tickets for the festival
- Discounts to participating local businesses
Routes:
The Trail Mix 2 Miler is a family-friendly fun run and walk on the trails. All ages and skill levels are welcome! This event isn’t timed. Instead of being a competition, the Trail Mix will focus on fun and camaraderie. Once you cross the finish line, it’s time to party! This two-mile event is perfect for…
- People getting into (or returning to) running
- Families – including little ones in strollers!
- Anyone who is new to trails
When you register four or more people for the Trail Mix 2-Miler, you’ll receive a $2.50 discount for each participant. The more the merrier! Please note that registration for the Trail Mix 2-Miler does NOT include a t-shirt or drink tickets.
Schedule
June 28th, 2026. The events will be staggered throughout the morning, and then we’ll put the “fest” in Trail Fest!
Bayside Ride: 8:00am
Trail to Ale 10K: 9:00am
Trail Mix 2 Miler: 9:30am
Location
38 Diamond Street
Portland, ME 04101
Cost
Price increases after May 31, 2026 at 11:59pm EDT.
Trail to Ale 10K: $60
Bayside Ride: $60
Trail Mix 2 Miler: $15
Volunteer
Interested in volunteering? We need great people to join our crew! Email fest@trails.org