Cumberland
Walking Events Calendar near Cumberland 2026-2027
Monthly updates for Cumberland
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Explore the top walking events near Cumberland for 2026-2027! We've gathered 17 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Walkers join the TD Beach to Beacon Walk, Run and Roll at Fort Williams Park, Shore Road, Cape Elizabeth. Routes run alongside the running and roll events and welcome athletes of all abilities.
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 can join the 3.5 mile Fun Walk from Old Town Hall, 181 Main Road on bridge accessible Westport Island, Maine, following Main Road onto Post Office Road. The route runs on island roads near pine and fir forests and coastal inlets, with ref..
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 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
Walkers can choose a timed or untimed 5K of 3.1 Miles from Hermit Island Campground in Phippsburg, ME along ocean trails with coastal scenery and low traffic. A virtual option lets walkers complete the distance during the week and timed heats use..
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..
December 2026
May 2027
July 2027