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  • 38 Diamond Street, Portland, Maine, 04101, United States
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    Distance: 903 m from Portland
    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
    2 Miles10kCyclingRunTrailWalk via RunSignup
  • Distance: 3.3 km from Portland
    Sun, Jul 12, 2026 at 12:00 AM

    What: The STRIVE for 5 5K Road Race and Fun Run hosted by the STRIVE Business to Business Networking Group, a collection of business leaders from the Foden Road/Maine Mall district of South Portland (business leaders from surrounding communities also welcome). Foden Road Networking Group members are invested in supporting the local economy and residents through business-to-business fellowship, culminating in the annual STRIVE for 5 5K.

    Proceeds benefit STRIVE, a nonprofit in the heart of the Foden Road district of South Portland. STRIVE engages and empowers 1,400+ young adults with developmental disabilities throughout Southern Maine through educational, social and employment training programs.

    When: Sunday, July 12th, 2026

    Children’s Fun Run begins at 8am, 5K/Walk Begins at 8:30am

    Rain or Shine

    Where: STRIVE, 28 Foden Road, South Portland ME 04106

    Entry Fee: $25 on or before 04/12. $30 on or before 07/10. $35 for participants signing up on 07/11 (day before/packet pick-up) or 07/12 (day-of).

    Participants 12 and under are free with an adult.

    Every participant receives a shirt from STRIVE and free admittance to all elements of the block party.

    Race Info: Children’s Fun Run will start at the STRIVE parking lot and go to the end of Foden Road (will be closed to traffic) before turning around to finish back at the parking lot. During the 5k, runners will line up and walkers will follow. The course runs from STRIVE on Foden Road through Texas Instruments’ Property onto Jet Port Plaza Road then circles back. Spectators can view the race on Foden Road & Jetport Road. Map available: www.pslstrive.org/STRIVEforFive

    Pancake Breakfast: Join us after the STRIVE for 5 for a Pancake Breakfast starting at 9 AM! Breakfast will include pancakes, sausage, fruits, and assorted toppings! $3 for runners/walkers and $6 for anyone else!

    Parking: Parking information available soon!

    Packet Pick Up: Friday. July 10th from 3pm-9pm at 28 Foden Road, South Portland AND Sunday, July 12th (race morning) from 7:00am-8:00am at 28 Foden Road, South Portland

    Awards: Presented to top male & female per age group: 12 and Under, 13-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70+.

    FMI: please contact STRIVE Program Director, Alex Woodhouse at (207)774-6278 or [email protected]

    See full details
    5kFun RunRunWalk via RunSignup
  • Distance: 8.2 km from Portland
    Sat, Jul 18, 2026 at 7:30 AM

    2026 - 13th Annual Race

    This race is in memory of Matthew Rairdon, whose life was tragically taken in November 2013. When preparing to go to college, Matt was extremely appreciative to receive a scholarship to attend St. Joseph's College. The intent of this scholarship fund is to help other people who want to pursue a nursing education at St. Joseph's. The first scholarship was awarded in the fall of 2014, and now we award 2 scholarships annually.

    Here are the details for this year's race:

    1. Packet Pickup will be done over 2 evenings, from 4-6 pm on Thursday, July 16th and Friday, July 17th at BreaLu, 511 Main Street in Westbrook.

    2. We have a water station on the course route.

    3. We will have an awards ceremony in the park after the race.

    4. "Matt's Mile" is a short fun run for children, located in the park. The race is for children age 10 and under and will be split into 2 heats: first 1-5 year olds, and then 6-10 year olds. If you want a t-shirt that is smaller than a Youth Small, please email us at [email protected] with your request. Make sure to write Matt's Mile T-Shirt Request in the Re: line.

    5. Well-behaved dogs are welcome on the course every year. We will have Westbrook Strong Dog Bandanas available for sale at packet pick up and in the park during race day. They are $5 each. You can pay with Venmo or cash.

    This year's charitable gift recipient will be Safe Voices. Safe Voices currently operates the only shelter and support services for victims of domestic violence and sex trafficking and exploitation in Androscoggin, Franklin, and Oxford counties. If you want more information on them, please go to their website: www.safevoices.org

    Thank you for 13 years of support - the Rairdon Family very much appreciates it. Westbrook Strong!

    See full details
    3.1 Miles5kFun RunRun via RunSignup
  • Distance: 4.5 km from Portland
    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
    1 Miles1.5 Miles4.5 MilesCyclingDuathlonKidsRunSwimTrailTriathlonVirtual via RunSignup
  • Distance: 5.1 km from Portland
    Sat, Jul 25, 2026 at 12:00 AM

    Enjoy a 5 mile loop around beautiful and scenic Peaks Island off of the coast of Maine.

    NO RACE DAY REGISTRATION. Please register by July 23, 2026

    1k5 MilesRun via RunSignup
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