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Walking Events Calendar near Sebago 2026-2027

Monthly updates for Sebago

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Explore the top walking events near Sebago for 2026-2027! We've gathered 17 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
The Save a Stray One Mile Walk offers a leisurely 1 mile route through downtown Freeport, starting at Morse Elementary School just behind L.L.Bean. It is dog friendly, good for chatting with friends, and day of registration is available at the Mo..
Walkers use the road course starting at St. Max Church (150 Black Point Road, Scarborough, ME) with options for 5K or the kids 1 mile route. Online registration is $30; day of is $35 or $30 with a food donation, alongside the running races.
The Open 5k 3.1 Miles is a walkable loop around the Cumberland fairgrounds at 197 Blanchard Rd, Cumberland Center ME, finishing on the horse track. Walkers share the course with mile races and the event includes a farmers market and music.
September 2026
Walkers follow a 5K trail through open fields, rolling hills and woods on Skyline Farm and Yarmouth Water District trails. A free Kids’ 1K runs alongside and food, music and family activities follow.
Walkers follow a scenic 2.5 Miles route along Portland's ocean side Back Cove Boulevard on the boulevard pathway. Registration and activities are offered before the event and controlled pets are welcome.
Walkers can choose Half Marathon or 5K, starting and finishing at Schouler Park on a fast, flat scenic course along West Side Road and the Saco River; no dogs or strollers.
Walkers can complete a 5k course around Maine Beer Company starting at 525 U.S. 1 in Freeport, ME. The event welcomes walkers alongside the running races and finishes at the brewery.
October 2026
A 5k walk starts and ends at Oxbow Beer Garden in Oxford on wooded ski trail Anne's Moon Dance to Moxie's Place, with restrooms on site and only trained service dogs allowed.
Walkers follow a 3.1 Miles route on the Bates College campus in Lewiston, starting at 2 Andrews Road and enjoying a beautiful campus route at their own pace. Registration fee is $20.
Walkers can take part in the Fitness Walk of 5k (3.1 miles) along Keoka Lake. The challenging out and back route features rolling hills and autumn lake scenery alongside the running races.
Walkers follow a 5k course at Allagash Brewing Company in Portland, ME. The in person event runs alongside runners and joggers and ends with a finish line celebration at the brewery.
Walkers use the official 5K Run/Walk course that starts and finishes at the Biddeford Primary School parking lot. The route follows Hill Street west to Forest, then Elm, Grayson and back to Hill along local streets alongside the running race.
November 2026
Walkers join the 2.5 Mile walk on arrival along the Bayside Trail, starting and finishing at the Sewage Treatment Plant Rd Bayside Trail entrance. Packet pickup is at Marathon Sports 309 Marginal Way and maps are provided; the finish is near Flee..
Walkers can choose the 1 Mile walk starting at Norway Fire Station, looping through downtown Norway and along Norway Lake. The course has a turnaround with a water station at the Wook Nook upper parking lot and runs alongside the running races.
December 2026
The event offers a 5K walk starting at 7 Nulty Street in Bridgton, Maine and an untimed kids fun run. Amenities for walkers include water, fruit, bathrooms, parking, hot cocoa and free finish line photos.
April 2027
The walk follows a 5K route from the Humane Society 55 Strawberry Ave along the Androscoggin Riverwalk to Sunnyside Park; dogs allowed if vaccinated and not on flex lead leashes.
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