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

    Sun, Apr 19, 2026 at 3:30 PM

    17.1 km from Windham
    575 Congress Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    Run Trail

  • 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!

    14.8 km from Windham
    15 Farm View Dr., Cumberland County, Maine, 04260, United States
    OpenStreetMap Google Maps

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

  • Shipyard Old Port Half Marathon & 5K [oldporthalfmarathon.com]

    Sat, Jun 06, 2026

    17.2 km from Windham
    433 Fore Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    5k Half Marathon Run

  • 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.

    16.3 km from Windham
    309 Marginal Way, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    5k Run Trail Virtual Walk

  • Sebago Lake Triathlon [tri-maine.com] [Register at runsignup.com]

    Sun, Jun 28, 2026 at 7:00 AM

    Description

    Offering both Sprint and Olympic distances race on beautiful Sebago Lake, the Sebago Lake Triathlon offers the premiere Maine race weekend . From the swim on the clean, clear water of Sebago Lake to...

    Offering both Sprint and Olympic distances race on beautiful Sebago Lake, the Sebago Lake Triathlon offers the premiere Maine race weekend . From the swim on the clean, clear water of Sebago Lake to the challenging bike course on country roads and run on trails across St. Joseph’s College, the Sebago Lake Triathlon promises you safe scenic races, great post race barbecue, professional announcer and music and more!

    The Sebago Lake Triathlon will take place at St. Joseph’s College.

    PLEASE DO NOT ARRIVE AT THE COLLEGE BEFORE 5:00a

    Sprint Swim:

    1/3 mile triangular course in beautiful Sebago Lake. Average water temperature is in the mid 60s at that time of the year.

    Olympic Swim:

    .9 mile swim in the calm basin of beautiful Sebago Lake. Average water temperature is in the mid 60s at that time of the year.

    Sprint Bike: 13.1 Miles

    Olympic Bike: 22.8 Miles

    Sprint Run: 5k course through the campus on wooded trails with many bridges. The red loop is fairly flat, but the blue finish loop will challenge you. There will be aid stations approximately every 1 mile.

    Olympic Run: 5.2 Miles

    Transition Area

    There will be one Transition Area adjacent to the finish. The transition area will open at 5:30 a.m. on Sunday (race morning) and will be closed approximately 15 minutes before the start of the first wave. Only volunteers, staff, and registered athletes are allowed into the Transition Area at any time. You must be body-marked before entering Transition (relays included), and have a safe, approved helmet and will have their bikes inspected for USAT compliance. Once you complete the race, you will not be allowed back into the Transition Area until all of the cyclists are back, or the bike time cutoff is reached.

    The Sebago Lake Triathlon will finish near the transition on the grass in front of Xavier Hall

    Relays:

    Relay members are required to hand off the timing chip after each leg of the race. The handoff takes place at their designated bike rack spot only. The cyclist cannot remove the bike from the rack before being tagged by the swimmer. The cyclist cannot tag the runner before re-racking the bike. The overall time for a relay will be the aggregate of times for each of the members.

    Timing

    Professional chip timing will be provided by All Sports Events. Every athlete and relay team will receive a timing chip to be worn around the ankle. Participants will receive times for swim, bike, run, T1, T2, and finish.

    Results

    Click here for results!

    Awards:

    Top 3: Male/Female overall

    Top 3 in each age triathlon category (19 and Under, then every 5 years up to 80 and over)

    Top 3: Male/Female overall Aquabike

    Top 3 Clydesadales (Men over 220 lbs) and Athenas (Women over 165lbs) (must be registered for this division)

    Top relay in each division (all-male, all-female, co-ed)

    Please note that age (and age group) is based on Dec. 31st of this year, NOT what your age is on race day.

    Packet Pick-up

    YOU MUST HAVE YOUR ID TO PICK-UP YOUR PACKET

    Friday, September 26 TBA

    Packet pickup Opens – Cyclemania 65 Cove St, Portland, ME 04101

    Cyclemania / Packet Pick-up Closes

    Saturday, September 27 TBA

    2:00 pm Packet Pickup Alfond Center St Joseph’s College opens

    4:00 pm Packet pickup Alfond Center St Joseph’s College closes

    Sunday, September 28

    5:30 am Packet Pickup Alfond Center St Joseph’s College opens

    6:30 am Packet pickup Alfond Center St Joseph’s College closes

    Post Race

    We will make every effort to have an awards ceremony in a safe way and hope this will be possible at the time of the event. A Post race celebration with music and refreshments. We hope to have a a fun, festive atmosphere celebration for the whole family where you want to stick around and hang out with your family and fellow triathletes, but we can’t know if this will be possible until closer to the event.

    Parking is conveniently located on campus a short distance from the transition area. PLEASE COME TO THE VENUE ONLY VIA Rt 302 to White Bridges Rd and turn right on to Wisteriea Way coming to campus and leave by making a left out of Wisterlea way. This will allow to you leave after your event is complete while we still have cyclists coming and going from campus. Thanks for your assistance making the event as safe as possible for all participants.

    USAT Sanctioning:

    The Sebago Lake Tri will be sanctioned by USA Triathlon. If you are not an annual member of USA Triathlon, you will need to purchase a 5 one-day membership as part of your registration.

    Rules:

    Please look over the rules - you are responsible for understanding them and abiding by them. They are available on the USA Triathlon website.

    Inclement Weather:

    There is NO rain date, We Go Rain or Shine. In the case of foul weather or inclement conditions, Acts of God, or other reasons the race cannot be executed as planned, management reserves the right to cancel, postpone, reschedule, switch to virtual for all participants, alter, modify the race / course, remove one or more of the legs (swim, bike, or run), or cancel the race altogether.

    In any case there will be No Refunds of race entry fees. Each athlete must except any such risk of their entry fee paid. There is no complementary race entry to a future race. All monies collected are used to develop and produce the event, including all race supplies, staffing, and administration. We pledge to make every effort to produce a fair, safe and exciting event for all and we will do everything in our power to prevent changes to the published race course and schedule; however, there are many factors and stakeholders involved. Any decision we make to go forth with the race is based on the overall event safety. In the case of a change or cancellation due to factors beyond our control, we are unable to offer any refunds for any entry, regardless of what type it is.

    The race has a no-refund policy (click here to read the specifics and reasons why). However, we understand that things come up and plans change. Therefore, we are offering a new option to purchase a “fully refundable entry” at the time you sign up, for an additional $25. This will provide peace-of-mind, knowing that your entire entry fee is refundable up until three days before the race

    16.5 km from Windham
    Standish, Maine, 04084, United States
    OpenStreetMap Google Maps

    Aquabike Cycling Duathlon Run Swim Trail Triathlon Virtual

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