Skip to main content

More cycling events nearby

  • Kennebec Savings Bank East Bayside Trail Fest [runsignup.com]

    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]

    4.9 km from Portland
    38 Diamond Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    2 Miles 10k Cycling Run Trail Walk

  • Portland Kids Duathlon [portlandkidsduathlon.com] [Register at runsignup.com]

    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/.

    3.2 km from Portland
    Portland, Maine, 04103, United States
    OpenStreetMap Google Maps

    1 Miles 1.5 Miles 4.5 Miles Cycling Duathlon Kids Run Swim Trail Triathlon Virtual

  • Maine Lighthouse Ride 2026 [runsignup.com]

    Sat, Sep 19, 2026 at 7:00 AM

    Join us for the 23rd Annual Maine Lighthouse Ride (MLR) on Saturday, September 19, 2026. True to its name, MLR highlights the breathtaking views of coastal southern Maine, including multiple

    lighthouses, rolling terrain, and stunning views of the Atlantic Ocean and the iconic Scarborough Marsh. MLR offers four ride lengths to challenge riders of all abilities – 25 miles, 40 miles, 62 miles, and 100 miles!

    This ride benefits the Eastern Trail Alliance, a nonprofit organization that builds, maintains, and promotes the Eastern Trail, southern Maine’s premiere multi-use greenway. ETA members use discount code Member2026 to save 10% off registration! Your registration fee includes the ride, well-stocked rest stops with yummy snacks, pickles, PB&Js, and more, and post-ride festivities including a meal and two beers.

    7.7 km from Portland
    2 Fort Road, South Portland, Maine, 04106, United States
    OpenStreetMap Google Maps

    25 Miles 40 Miles 62 Miles 100 Miles Cycling Trail

  • Portland Velo Club (PVC) 2026 Membership [portlandvelo.com] [Register at bikereg.com]

    Sat, Oct 31, 2026 at 11:59 PM

    4.9 km from Portland
    65 Cove Street, P.O. Box 15093, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    Cycling

More cycling events nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.