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  • 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]

    23.3 km from Freeport
    38 Diamond Street, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    2 Miles 10k Cycling Run Trail Walk

  • 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/.

    22.8 km from Freeport
    Portland, Maine, 04103, United States
    OpenStreetMap Google Maps

    1 Miles 1.5 Miles 4.5 Miles Cycling Duathlon Kids Run Swim Trail Triathlon Virtual

  • WEEKLY BACK COVE SERIES 2026 [backcove.runtowin.com] [Register at raceroster.com]

    Wed, Aug 26, 2026 at 6:00 PM

    Weekly Back Cove Series Rules

    The Back Cove Weekly 5k Series registration requires the same donation no matter what point of the series that registration takes place. Registration costs a flat rate

    of $50 and only needs to be paid once whether you run 1 race or all 14.

    A portion of each registration fee is donated to Portland Trails and A Running Passion!

    Registration is online only. Prior to your first race, you can pick up your bib in the Portland Store for the week from May 20th at 10am through Wednesday, May 27th at 4pm during store hours. If you aren't able to pick up your bib at the store before the series starts, you can pick your number up at the Back Cove before the start of each race from 5:15pm until the race starts at 6pm or during our regular business hours.

    Please keep your bib for the entire series as you will only receive 1 bib!

    T-Shirts can be added to your registration at a $10 charge. New for this year is a season finisher hoodie option. Run all 14 races and receive a free WBCS series finisher hoodie for your fall adventures!

    See the check the map for details.

    Due to city requirements, we may only have 250 participants in each Wednesday Back Cove 5k. Registered runners will be required to check-in on line each week. Check-in begins on Saturday morning at 8:00 am and continues until Wednesday at 2:00 pm or until capacity reaches 250, whichever comes first. Check in will be closed at that time. See below for directions on the check-in process.

    Please note, if you do not plan on running, please do not check in! If you run in the weekly Back Cove without checking in, you risk having the event cancelled. Please respect this request and don’t run if you are not checked in!

    The entire series is treated as one event. Once you register, and pick up your race number, keep your WBCS number and visibly wear it. Your race number is how we identify you.

    Please keep your WBCS race # for the entire Summer series!

    June 3rd is Global Running Day at Marathon Sports! As in previous years, we will use the Weekly Back Cove Series as our race portion, the course distance is 5K and will begin at 6pm. We will also offer a casual group run, about 3-5 miles in distance, leaving directly from our Portland location at 6pm. No registration is required for the group fun run but you must be registered and checked in to participate in the Back Cove race.

    After both the Weekly Back Cove Series and our group fun run, everyone will meet back at Marathon Sports- Portland for refreshments and socializing. We hope to see you on June 3rd!

    2026's Themed Races:

    • June 10th - Nowhere To Wear This (Its been sitting in your closet waiting for this race cause where else would you wear it?)

    • June 24th - Rainbow Run (How many colors can you represent in one race outfit?)

    • July 8th - What's Your Favorite Movie (Dress like a character from your go to movie!)

    • July 22nd - Hawaiian Shirts Only (Well not ONLY but strongly encouraged!)

    • August 5th - Twinning Day (Find your run bestie and coordinate your race day drip!)

    • August 19th - Fancy Day (We are almost to the end of summer, lets celebrate in some upscale style!)

    Awards

    Grand Prix Series – open male/female top 6 times with lowest cumulative time receives 2 pairs of running shoes courtesy of Marathon Sports!

    Age Group Awards - Age group winners based on top 6 times with lowest cumulative time receive a $50 Marathon Sports certificate. Age is determined on the date of the last race of the season, and the categories are:

    • 13 and under

    • 14-19

    • 20-29

    • 30-39

    • 40-49

    • 50-59

    • 60-69

    • 70 and over

    Maine Track Club Running Community Spirit Award – will be awarded to a participating individual or individuals who represent the “Community Spirit” of the Back Cove Series for commitment, improvement, determination and dedication to the event!


    Results will be posted here at the website.

    For more information call Marathon Sports Portland at 207-773-6601 or go to backcove.runtowin.com.

    Check-In Process

    The maximum number of runners each week is 250. So far, 250 runners have checked in for the next race.

    To Check-In, click on the link to your individual race results which should have been emailed to you when you registered. You can also check the complete runners list and click on your name there in to reach that page.

    Once there, you will see a list of all of this year's races. Each week, the next race will have a button next to it that will look like one of the following:

    • Check-In Not Yet Open...

    This button means that the check-in process for the next race has not yet started. Check back on Saturday morning at 8:00 to check-in.

    • Click to Check-In...

    This button means that check-in has opened for this week and there are spots available. Click this button in order to check-in. If check-in is successful, the button will change to:

    • You are checked in!

    This button means that you have checked in for the week and can come to the next race.

    • Race Limit Reached!

    This button means that you missed the check-in period, either because our race capacity for the week has been reached or because it is after 2:00 in the afternoon on the day of the race.

    Please remember that the city is limiting our number of participants each week and if you don't check-in but race anyway we may have to cancel the series. Please only come to the race if you have successfully checked-in. Thank you!

    23.8 km from Freeport
    Back Cove Trail, Portland, Maine, 04101, United States
    OpenStreetMap Google Maps

    5k Fun Run Run Trail

  • Last Man Standing Ultramarathon [lastmanultra.com] [Register at runsignup.com]

    Sat, Sep 05, 2026 at 12:00 PM

    Last Man Standing Ultramarathon is a backyard ultra race held on the pristine, wooded trails of Pineland Farms in New Gloucester, Maine. The course is a 4.2 mile loop with double track and some

    moderate elevation gain.

    The LMS course is as inviting as it is challenging. Those who are new to trail running and the backyard ultra format may find themselves completing new personal best distances. Trail veterans will push against their toughest limits and break through them!

    16.1 km from Freeport
    Oak Hill Trail, Cumberland County, Maine, 04260, United States
    OpenStreetMap Google Maps

    Backyard Ultra Marathon Run Trail Ultra

  • Farm to Farm Ultra [runsignup.com]

    Mon, Sep 14, 2026 at 12:00 AM

    The Farm To Farm Ultra Run is held on a looped course in Freeport, Maine on the Wolfe's Neck Center & Freeport Conservation Trust trails, but also includes four virtual options: 5 miles, 10 miles, 30

    miles, and 50 miles. This event is part of the Maine Track Club Grand Prix Series, and participants are allowed to earn points for one virtual event in addition to or instead of the in-person race. If you intend to do both in-person and virtual, you must register separately for each event.

    Click here to register for the in-person race on Sunday, Sep. 27 2026

    The entry fee for each virtual event is $25, with no t-shirt included.

    If you would like a shirt, please contact us! They are 15$ for local pickup (greater Portland area) or 20$ to ship.

    Participant will have from Sep. 14 2026 to Oct. 12 2026 (Indigenous Peoples' Day) to complete their chosen distance(s) and submit results.

    654 m from Freeport
    184 Burnett Rd, Freeport, Maine, 04032, United States
    OpenStreetMap Google Maps

    5 Miles 10 Miles 30 Miles 50 Miles Run Trail Ultra Virtual

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