5 running, walking, cycling, and other events in Kennebunkport, Maine
From big races to Saturday morning group runs—find running, walking, cycling, and fun run events and connect with the local endurance sports community.
Kennebunkport
5 events in Kennebunkport-
Sun, Jun 07, 2026 at 9:00 AMSee full details
Join us for a festive day along Maine’s southern coast to celebrate cycling, walking, good food, and community. Your support of this fundraising ride directly supports the Bicycle Coalition of Maine’s work to support safer streets for all.
We’re offering three ride options for 2026!
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17 mile, family-friendly ride,
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33 mile, enough without too much,
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53 mile, extended coastal tour (this route is subject to change)
All routes include a rest stop, beautiful oceanside views, and a finish line post-ride celebration at the Kennebunkport Conservation Trust with live music and games for all.
Above registration fees include 100% of BikeReg service fees.
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Sun, Jul 05, 2026 at 9:00 AM
Sunday, July 5th, 2026.
The race will start at the Community House at 9am! Number pick-up will be day of the race beginning at 8am. T-shirts will be distributed on race day to all registered runners.
Online registration ($45) will be open until midnight on July 1st. After that time you must register in person on race day ($50). Race day registration will begin at 7:00am on July 5th.
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Sun, Aug 09, 2026 at 9:00 AM
Pick from a 5k or 10k. The courses wind through our beautiful trail system and end at our headquarters with a party you won't want to miss! The events will feature music all day, a beer tent, delicious food and games for the whole family!
Everyone who registers before noon on July 15 gets a shirt!
Check in and day-of registration begins at 9:00 AM, and the races start at 10:00 AM.
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Sat, Oct 03, 2026 at 10:00 AM
The Bobcat Ridge 25K is a 25K trail race on the beautiful trails of the Edwin L. Smith Preserve, with all proceeds going directly to the Kennebunkport Conservation Trust
Please note: registration is capped at 100, and the cutoff for shirt-included registration is Saturday September 5th
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Sat, Oct 31, 2026 at 10:00 AMSee full details
Please join us at the beautiful Emmons Preserve in Kennebunkport for the 4th Annual Holistic Hustle. There will be music all morning with a timed 5K and 10K run/walk and a kids 1/2 mile fun run and all participants will receive a unique wood burned finishers medal! We will award first place overall male/female in the 5K and 10K.
Check out our great venue and trail maps here: Emmons Preserve.
Everyone is welcome to take part in the music, face painting, yard games and refreshments, anyone for Congdon's doughnuts, cookies, hot chocolate and wicked Joe coffee?
All participants will receive a raffle ticket to our awesome raffle filled with great prizes and local gift cards (some valued up to $250)! Extra raffle tickets will be available for purchase at the event.
Schedule of events:
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9:00 registration opens
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10:00 10K Run
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10:10 Kids Fun Run
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10:30 5k Run/Walk
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11:30 Awards and Raffle
About Us:
School Around us is a 501C(3) Co-Learning community founded in 1970, serving students ages 5 to 14, with the aim of embodying the philosophy of holistic & environmental education. We believe that as learners we develop meaning, identity, and purpose through self-discovery, relationships, a lifelong connection to the environment and accountability to our community.
The Hustle for Holistic Education will be an opportunity for the school community, extended family and friends and the surrounding community to come together to support lifelong learning, a love for the outdoors and holistic education. We anticipate upwards of 100 participants to support our mission.
Note that the Family Rate of $60 will be applied at checkout (for families registering 3-8 people).
There are three key ways you can support the School Around Us and our 4th annual Hustle event:
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Join Us for a Run / Walk on Saturday, November 1, 2025. There is a 5K, 10K and kids fun run.
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Donate! Make a tax deductible donation to our 501(c)3 to help further our mission. You don't need to participate in the run to show your love & support by following and sharing THE DONATE LINK
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Share the link to our fundraiser on social media to drive more awareness of our event and help in our fundraising efforts.
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