Westport
Walking Events Calendar near Westport 2026-2027
Monthly updates for Westport
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Explore the top walking events near Westport for 2026-2027! We've gathered 158 great walks in the area. Check out our detailed list below to find your next local walk.
April 2027
Walkers can use the 4 Mile course, flat with a scenic start and finish on the Great South Bay at East Islip Marina; strollers free, baby must be registered and start at back.
May 2027
Walkers can follow the 5K course starting at The Mary Louis Academy in Queens, with a mapped route available online. Amenities for walkers include free finish line photos, live, text and email results, and in person or virtual bib pickup with per..
Walkers follow the 5K course at Caumsett State Park in Lloyd Harbor, with free park fees for entrants, snacks and a nutrition table, plus early and onsite bib pickup.
The event offers a 5K walk on park paths at Heckscher State Park in East Islip; strollers are welcome, dogs are not allowed near the path or picnic area, parking costs $8 and finish line photos are free.
Walkers can complete a 5K on local streets starting and finishing at Oyster Bay Brewing Company parking lot with U turns and no strollers or pets allowed.
Walkers can join the 5K course starting at Huntington YMCA on Main Street, with on site bib pickup at the Pavilion and post event refreshments alongside the running races.
A 5K walk on Court House Drive in Central Islip starts at the crosswalk across from the Islip Town Fire Museum and offers free finish line photos and personalized bib options.
Walkers can join the 5K at Glen Cove High School, 150 Dosoris Lane, Glen Cove NY, on a mapped course alongside the running races. Pre race and day of bib pickup are available at the YMCA and at the high school, with post race refreshments and fir..
Walkers follow a 1.55 mile loop twice for a 5K, starting at Hillside Avenue and 136th Street on an out and back along Kew Gardens Road with a gradual hill; stay on the far right as marshals guide the course.
Walkers can use the single loop 5 km course around Brightwaters starting at Walker Beach; the 10 km option is for runners only. The road course runs along Montauk Highway with rolling closures, a dedicated bike area for locals, and bib pickup..
Walkers may lap a single and double track 2.2 mile loop with roots, rocks, rolling hills and 131 ft gain; pavilion aid and porta potties at 700 Peters Ln Stratford CT.
Walkers can do the 5K at Bethpage State Park over grassy polo field and scenic soft trails with few small hills, beginner friendly, with free finish photos and live results.
5K walk through gardens and trails at Planting Fields Arboretum in Oyster Bay. Registrants also have a 1/2 mile Kids Fun Run alongside the running races and access to free self guided tours, food trucks and finish line photos.
MS Health Walk is based at Lewisboro Library in South Salem on village and road courses with parking at the library and online course maps, held alongside the race events.