Westbrook
Walking Events Calendar near Westbrook 2026-2027
Monthly updates for Westbrook
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Explore the top walking events near Westbrook for 2026-2027! We've gathered 46 great walks in the area. Check out our detailed list below to find your next local walk.
May 2027
Walkers can choose an untimed John May Mile fitness walk or the 5K across the Peconic Landing campus in Greenport, NY. Strollers, baby joggers, rollerblades, skates and pets are not permitted on the course.
Walkers can do a 5K course starting at Greenport High School on Front Street in Greenport, with on course water stations, restrooms and free finish line photos alongside the run.
Walkers can join the 5K course that starts at The Bridgehampton Museum on Montauk Highway with parking on the museum grounds. Amenities include free finish line photos, live text and email results and in person bib pickup about one hour before th..
June 2027
Ramble walkers follow trails through high meadows, woods and fields starting at Coogan Farm, with separate registration required; strollers and other equipment are not allowed.
Walkers can choose the 10 km or 5 km routes on a scenic Shelter Island course starting at Shelter Island Union Free School District, 33 N Ferry Road. Routes include water stops, a ferry shuttle between ferries and the race site, and a staffed..
July 2027
Walkers can enjoy a 3 Mile walk starting and finishing at Agawam Park in beautiful Southampton. All participants receive a tech tee and light refreshments, with registration and bib pickup held on the morning of the event.