7 events in Cumberland County, Maine

From big races to Saturday morning group runs—find 5k events and connect with the local endurance sports community.

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

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

  15 Farm View Dr., Cumberland County, Maine, 04260, United States
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• Race for Recovery 5K [runsignup.com]
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  Sun, Jun 28, 2026 at 8:00 AM

  Description

  Race for Recovery 5K

  Race benefits "Tucker House"

  Sunday June 29th 7AM packet pick up

  $20 Pre-Registration

  $25 Race Day Registration

  7AM-8AM at Harrison Post Office 5 Front St Harrison, Maine

  Race Start is at Tie Up. Race start Time at 8am

  First 50 registrants receive a t-shirt.

  3.1 Miles 5k Run

  5 Front St, Cumberland County, Maine, 04040, United States
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• 4th Annual 5K Race for Recovery [runsignup.com]
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  Mon, Jun 29, 2026 at 8:00 AM

  Description

  Registration Opens March 16th, 2026

  Race for Recovery 5K benefits "Tucker's House" in Bridgton and Harrison Maine.

  Sunday June 28th 7am packet pick-up.

  $20 Pre-registration

  $25 Race Day Registration

  Meet at Harrison Post Office, 5 Front St, Harrison, ME between 7am and 8am.

  The race will begin at 8am promptly at the Tie Up General Store in Harrison.

  The first 50 Registrants receive a t-shirt.

  5k

  5 Front St, Cumberland County, Maine, 04040, United States
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• Sebago Days 5K [runsignup.com]
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  Sun, Jul 19, 2026 at 8:00 AM

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  The 47th annual Sebago Days celebration will again include a road race open to both runners and walkers. It'll be a 5-kilometer out-and-back course on Route 11, starting near the intersection of...

  The 47th annual Sebago Days celebration will again include a road race open to both runners and walkers. It'll be a 5-kilometer out-and-back course on Route 11, starting near the intersection of Route 114, and the course will be closed to traffic.

  T-shirts to the first 150 entrants in the 5K.

  Registration through March 31 is $25. The entry fee for adults increases to $35 on April 1 but remains $24 for ages 17 and under, and race-day registration for everyone is $40.

  No preregistration is required for the free 50-yard toddler dash at 7:50 a.m.

  Awards for top three overall males and females, and first place in the following male and female categories: Overall, 10 & under, 11-13, 14-17, 18-29, 30-39, 40-49, 50-59, 60-69, 70 & over.

  Packet pickup and registration will be available Saturday, July 18, at the Sebago Days information tent next to the raffle camper.

  5k Run Walk

  Cumberland County, Maine, 04029, United States
  OpenStreetMap Google Maps
• Crooked River 5k [lelt.org] [Register at ultrasignup.com] - Facebook - Instagram
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  Sun, Jul 26, 2026 at 9:00 AM

  5k

  244 Scribners Mills Rd, Cumberland County, Maine, 04040, United States
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• UCan 5k - Raymond, Maine [runsignup.com]
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  Sat, Aug 29, 2026 at 8:00 AM

  Description

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  UCan 5K & Kids Fun Run – A Community Tradition Continues

  Join us on Saturday, August 29th as we proudly host the second year of the revived UCan 5K, a cherished community tradition held in loving...

  UCan 5K & Kids Fun Run – A Community Tradition Continues

  Join us on Saturday, August 29th as we proudly host the second year of the revived UCan 5K, a cherished community tradition held in loving memory of Candace Woolston. This meaningful event celebrates community spirit, wellness, and the enduring legacy of a beloved community member.

  Participants will enjoy a scenic 5K course showcasing the natural beauty of Raymond, including picturesque views of Sebago Lake. The race will begin and end at Sheri Gagnon Memorial Park, traveling along familiar local roads that make this event both memorable and enjoyable for runners and walkers of all abilities.

  In addition to the 5K, we are excited to offer a Kids Fun Run prior to the main event—providing our youngest community members an opportunity to participate and promote healthy, active lifestyles.

  Proceeds from this year’s UCan 5K will directly benefit four outstanding organizations dedicated to strengthening our community.

  We invite you to run, walk, and rally around this special cause as we continue building momentum in the second year of bringing this important tradition back to Raymond.

  Registration is now open. Shirts are not guaranteed for participants who register after August 1st.

  5k Fun Run Run Walk

  63 Mill Street, Cumberland County, Maine, 04071, United States
  OpenStreetMap Google Maps