Cycling in Portland, Maine | 2026-2027

Kennebec Savings Bank East Bayside Trail Fest [runsignup.com]
Sun, Jun 28, 2026 at 8:00 AM
Description
Get active on the trails that make Portland so awesome.

On Saturday, June 28th, join us for the second annual Kennebec Savings Bank East Bayside Trail Fest! Be part of this community-wide event that...
Get active on the trails that make Portland so awesome.

On Saturday, June 28th, join us for the second annual Kennebec Savings Bank East Bayside Trail Fest! Be part of this community-wide event that brings hundreds of runners, bikers, and walkers together on the trails. Then celebrate with one another at a party featuring music, food trucks, local beer, and more!

This one-of-a-kind event in the heart of Portland's East Bayside neighborhood has three activities you can choose from to celebrate and support your local trails:
- Trail to Ale 10K
- Bayside Ride
- Trail Mix Two-Miler
The events will be staggered throughout the morning, and then we'll put the "fest" in Trail Fest!

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!

Thank you to our title sponsor, Kennebec Savings Bank, for making this community event possible!

Interested in volunteering? We need great people to join our crew! Email us at [email protected]
2 Miles 10k Cycling Run Trail Walk
38 Diamond Street, Portland, Maine, 04101, United States
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Portland Kids Duathlon [portlandkidsduathlon.com] [Register at runsignup.com]
Sun, Jul 19, 2026 at 7:00 AM

Description

About the Race

Portland’s first multisport race for children, The Portland Kids Duathlon, is presented by Benchmark Real Estate. The race gives young people ages 3-12 an opportunity to participate in...

About the Race

Portland’s first multisport race for children, The Portland Kids Duathlon, is presented by Benchmark Real Estate. The race gives young people ages 3-12 an opportunity to participate in the fast-growing world of multi-sport racing. The run, bike, run format of a duathlon is fun and approachable, a great race for non-swimmers and triathletes alike. A bike only event for our youngest athletes as well as those with special needs makes the event even more accessible. All young athletes will finish the race with a smile on their face, a medal around their neck, and a boost of self-confidence and pride. All profits from this race will be donated to the Foundation for Portland Public Schools. Both in-person and virtual race options available.

Course

Transition will be at the triangle in front of Payson Park with separate transition areas for each race. We are on Baxter Boulevard with out-and-back bike courses on the road and out-and-back runs on the trail. Courses will parallel each other to make for easy viewing for spectators. All roads will be traffic free.

NOTE: All participants will need to purchase an annual membership with the USA Triathlon (USAT) for an additional $10. This is because our race is sanctioned and supported by USAT. See details below. USAT has now made this a one time fee.

About USAT

The Portland Kids Duathlon is USA Triathlon (USAT) sanctioned event. This means that not only do you have the confidence to know that the race will be safe, sanctioned, and insured but also that we follow a uniform set of rules with other USAT events. The term “sanction” refers to the compliance of a multisport event to USA Triathlon’s safety requirements. Safety plans, course maps, and event details must be submitted for review by USA Triathlon staff. It further requires our race director undergo an annual background check and maintain a certification from the U.S. Center for SafeSport. As a member, you also have access to discounts from many of USAT's partners including sports related products and travel companies. Those are found once you've created an account and then added and logged in to your child's account at https://member.usatriathlon.org/.

1 Miles 1.5 Miles 4.5 Miles Cycling Duathlon Kids Run Swim Trail Triathlon Virtual
Portland, Maine, 04103, United States
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2 cycling events in Portland, Maine

Description

Description

Local Clubs & Organizations