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4 cycling events in Portland, Maine

From big races to Saturday morning group runs—find cycling events and connect with the local endurance sports community.

4 events

Portland

4 events in Portland
  • Wed, Jun 03, 2026 at 6:00 PM

    Meet Lindsay of Still Peaking, LLC at Allspeed Cyclery in Portland, Maine for a monthly ride just for the ladies. Each session begins with a microdose of skills instruction to enhance your on trail experience. Ride concludes with a Chill & Grill session provided by Allspeed Cyclery.

    All bodies, abilities and fitness levels are welcome to join!

    Riders under 18 must be accompanied by a parent or guardian.

    See full details
  • 38 Diamond Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps
    Sun, Jun 28, 2026 at 8:00 AM

    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]

    See full details
  • Wed, Jul 15, 2026 at 6:00 PM

    Meet Lindsay of Still Peaking in Portland, Maine for this monthly ride w/ Allspeed X Wild Rye! Each session begins with a microdose of skills instruction to enhance your on trail experience. Ride concludes with a Chill & Grill session provided by Allspeed Cyclery. This month we will enjoy a presentation by Desirae LeBlanc, owner of Cadence Pelvic Health & Wellness.

    All bodies, abilities and fitness levels are welcome to join!

    Riders under 18 must be accompanied by a parent or guardian.

    See full details
  • Sun, Jul 19, 2026 at 7:00 AM

    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/.

    See full details
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