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  • Distance: 7.3 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: 3.2 km from Portland
    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
    CyclingMountain BikingTrail via BikeReg
  • Distance: 5.5 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: 8.6 km from Portland
    Sat, Jul 18, 2026 at 8:00 AM

    The Peaks to Portland Swim to Benefit Kids is one of the oldest open water swims in the world; since before World War II thousands have braved Maine’s waters to swim the 2.4 miles from Peaks Island to Portland’s East End Beach.

    2.4 MilesKidsOpen WaterSwim via RunSignup
  • Distance: 8.6 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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