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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]

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

    2 Miles 10k Cycling Run Trail Walk

  • Women’s MTB Ride w/ Allspeed X Wild Rye [stillpeaking.com] [Register at bikereg.com]

    Wed, Jul 15, 2026 at 6:00 PM

    11.3 km from Scarborough
    936 Brighton Ave, Portland, Maine, 04102, United States
    OpenStreetMap Google Maps

    Cycling Mountain Biking

  • 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/.

    14.3 km from Scarborough
    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.

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

    25 Miles 40 Miles 62 Miles 100 Miles Cycling Trail

  • 2026 ACT Trail Fest [arundeltrust.org] [Register at raceroster.com]

    Sat, Sep 26, 2026 at 9:00 AM

    Arundel Conservation Trust

    6th Annual Trail Fest

    September 26, 2026

    First race begins at 9:00 am

    Join the Arundel Conservation Trust Community on Saturday, September 26th for a race through our

    trails!

    Trail Fest features a 5k, 10k and a half marathon trail race. This event is in proud partnership with our sister organization, the Kennebunkport Conservation Trust who is hosting their annual Trail Fest on August 9th, 2026.

    Half Marathon: 9:00am

    10k Race: 10:00am

    5k Race: 10:30am

    The courses are set on the beautifully maintained ACT Multi-Purpose Trail and the Eastern Trails with stunning woodland and stream views. Runners will start at the new Arundel Municipal Building parking lot on 257 Limerick Road. All participants receive a medal and a t-shirt! There will be a live band and great food - come join the fun!

    All races return and finish at the Arundel Municipal Building parking lot. Please visit our website for parking information.


    Advance registration will close on September 25 at noon. You may register in person on race morning.

    We will be taking photos at this event to share on our social media channels for ACT promotion.

    22 km from Scarborough
    257 Limerick Road, York County, Maine, 04046, United States
    OpenStreetMap Google Maps

    5k 10k 21k Cycling Run Trail

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