Westport Island
Walking Events Calendar near Westport Island 2026-2027
Monthly updates for Westport Island
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Westport Island for 2026-2027! We've gathered 12 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 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..
An untimed 1 Mile walk at Medomak Valley High School in Waldoboro follows a one mile loop over stone dust trail and grassy field, perfect for a nature walk, with raffles for walkers alongside the 5k event.
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..
May 2027