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  • Trail Running Film Festival - Portland, ME [trailfilmfest.com] [Register at ultrasignup.com]

    Sun, Apr 19, 2026 at 3:30 PM

    24.6 km from Freeport
    575 Congress Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    Run Trail

  • The Polar Bear Triathlon and Duathlon [runsignup.com]

    Sat, May 02, 2026 at 8:25 AM

    Description

    The Polar Bear Triathlon / Duathlon will take place on its traditional date of May 2, 2026

    The Polar Bear Triathlon / Duathlon is New England’s season opening event! A sprint triathlon and duathlon...

    The Polar Bear Triathlon / Duathlon will take place on its traditional date of May 2, 2026

    The Polar Bear Triathlon / Duathlon is New England’s season opening event! A sprint triathlon and duathlon perfect for beginners and experienced triathletes alike combining a pool swim, a scenic bike course on country coastal roads, and epic and fast run on wide hard packed trails and quiet neighborhood streets,

    8:25a Start Time

    The Polar Bear Triathlon and Duathlon takes place the first Saturday of May annually to open the triathlon season in New England. The race is contested on the beautiful campus of Bowdoin College with world class facilities including a 16 lane pool, locker rooms with showers (pending availability), wonderful flat grass transition area and world class event production. This pool swim triathlon is a great race for beginners to get their feet wet and seasoned triathletes to start their season without the concerns of a cold, open water swim.

    Distances

    525 yard swim OR 2 mile run for duathletes

    11.5 mile bike

    3 mile run

    Virtual participants compete them all at once, or separately, it’s up to you. Swag will be mailed after May 4th to all virtual participants.

    The Polarbear Triathlon / Duathlon will be sanctioned by USA Triathlon. If you are not an annual member of USA Triathlon, you will need to purchase a $15 one-day membership when you register.
    12.4 km from Freeport
    35 Watson Dr, Brunswick, Maine, 04011, United States
    OpenStreetMap Google Maps

    Duathlon Open Water Run Swim Trail Triathlon Virtual

  • Buttermilk Mountain Backyard Bash [runsignup.com]

    Sat, May 09, 2026 at 7:00 AM

    Description

    A backyard-style run-til-you-stop ultra race at Kate Furbish Preserve East in Brunswick, ME.

    Join us for a long, fun, hard day of running on coastal Maine trails on May 9, 2026! Sample some of the...

    A backyard-style run-til-you-stop ultra race at Kate Furbish Preserve East in Brunswick, ME.

    Join us for a long, fun, hard day of running on coastal Maine trails on May 9, 2026! Sample some of the finest single and double track Buttermilk Mountain (elevation 121ft) has to offer. Nutrition: not provided. PFAS: guaranteed. Stoke: High.

    What is a backyard race? Run a 4.17 mile lap on the same course every hour on the hour. If you don't finish a loop within the hour, you are out of the race. 12 hour cutoff time for a maximum of 50 miles of running.

    The race is open to all experience levels! Run as many or a few loops as you like. Whether you're a lactate demolishing machine planning to finish the full 50, or a casual trail runner who wants to put in a few hours outside on a beautiful day, this event is for you.

    The race course is about a 12 minute drive from Bowdoin's campus.

    The $20 registration fee will go towards race expenses, and the rest will be donated to Preble Street nonprofit. If the registration fee poses a financial barrier to your participation, email tmooney@bowdoin.edu & fperez@bowdoin.edu.

    See you there.
    12.3 km from Freeport
    Brunswick, Maine, 04011, United States
    OpenStreetMap Google Maps

    50 Miles Run Trail Ultra

  • Trail Festival at Pineland Farms [trailfestpineland.com] [Register at runsignup.com]

    Sat, May 23, 2026 at 6:00 AM

    Description

    The premier trail running festival in Maine returns for year 3 with long runs on Saturday, shorter distances on Sunday, and a Sunset 5k and 24 hour solo and team events in between!

    It's time to mark Memorial Day weekend 2023 on your calendar and start training!
    17 km from Freeport
    15 Farm View Dr., Cumberland County, Maine, 04260, United States
    OpenStreetMap Google Maps

    5k 10k 15k 25k 50k 100k Run Trail

  • Luv 2 Run Portland 5K [runsignup.com]

    Sun, Jun 14, 2026 at 9:00 AM

    Description

    Luv 2 Run Portland 5K Walk/Run

    WALKERS WELCOME

    The Luv2Run Portland 5K Race is running the old fashioned way --- scenic off road courses --- great competition --- no rock bands --- fresh fruit &...

    Luv 2 Run Portland 5K Walk/Run

    WALKERS WELCOME

    The Luv2Run Portland 5K Race is running the old fashioned way --- scenic off road courses --- great competition --- no rock bands --- fresh fruit & pastries --- no squeezable yogurt --- beautiful T-Shirts --- useful awards (pint glasses) --- plain water, not flavored water --- plus bad jokes by the race director before and after the race!!!

    CASH PRIZES FOR OVERALL WINNERS

    Sunday June 14th, 2026 9AM Back Cove Trail, Portland, ME*

    Packet Pickup and Race Day Registration 7:30-8:45AM at Marathon Sports 309 Marginal Way Portland, Maine

    Directions to Start: 84 Baxter Blvd Portland

    $26 Wicked Early Bird Pre-Registration by January 1st $29 Early Bird Registration by April 1st--- $34 Thereafter--- $39 Race Day

    Race Makes Donations to: “Sons of the Amvets Michael Shone Scholarship”

    Colorful Luv2Run T-Shirts to entrants by May 10th, as available after this date.

    Luv2Run Pint Glasses Top Male/Female Overall & Top 2 Male/Female Age Groups

    Team Prizes to 1st Running Club, Corporate or Open Teams of 4 or more people.

    50/50 Raffle $2 Per Chance

    New for 2024 all participants 21+ may receive one (1) complimentary Mimosa at the post-race party (non-alcoholic Mimosas available as well).

    Post-Race Party at Charles J Loring Amvets Post 25 186 Washington Ave Portland 10:30AM. All under 21 must stay with parent.

    For more information E-mail: Tonedog86@aol.com

    **Due to recent changes in fee structures in the City of Portland and to keep race entry fee reasonable, packet pickup is 0.4 miles away from the finish and 0.9 miles away from the start. Maps will be provided. Driving time is less than 5 minutes from each location. There will be 15 minutes between closing of packet pickup and race start to allow runners to assemble.

    No Refunds. In the event of catastrophic weather, a public health crisis, or extreme events beyond race managements’ control every effort will be made to hold the race on an alternate date. If this is not possible, the race will be transformed to a virtual event where participants run the course & submit their results on their own.
    24.3 km from Freeport
    309 Marginal Way, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    5k Run Trail Virtual Walk

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