Shelter Island
Walking Events Calendar near Shelter Island 2026-2027
Monthly updates for Shelter Island
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Explore the top walking events near Shelter Island for 2026-2027! We've gathered 25 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Walkers can take part in the 5K route starting at Westhampton Beach Village Marina along a mapped course through the village. Packet pickup and race day registration are at the marina, with parking at the south end of the marina or behind Main Stre..
A non competitive 2 miles walk starts and ends at the Town Dock, 1 High St in Stonington. The course uses sidewalks or street edges, with two water stations and volunteers with flags guiding walkers while traffic shares the route.
The event offers a 5K walk starting at LYSB at 59 Lyme Street in historic Old Lyme, on scenic roads that wind through the village. Pre race packet pick up is available at LYSB, on site registration is accepted up to race day, and tee shirts go to..
August 2026
Walkers follow a 2.5 Mile scenic trail at Wildwood State Park in Wading River, NY alongside the trail run. Personalized bibs are offered with registration three weeks in advance and finish line photos are free; the event runs rain or shine.
Walkers can join a certified 5K loop through Stonington Borough with runners in a single mass start. The course starts on Main Street by the Stonington Free Library with on street parking, packet pickup and post race food and drink.
September 2026
Walkers can choose the 3 Mile route that starts and finishes at Agawam Park in Southampton, a park setting. Packet pickup and race day registration are available the morning of the event, and walkers receive light refreshments, a Dri Tech tee and f..
Walkers follow the USATF certified 5K road course starting at Devitt Field at Southworth and Belmont, along Main Street and Kirtland toward River Street, then back via Elm and Union to Devitt Field. The event is a 5K Run/Walk with electronic chip..
Walkers follow the 5K course at Westhampton Beach Village Marina in Westhampton Beach NY through a village marina setting. There are well stocked water stations at each mile marker, post race beverages and snacks, and first aid with ambulance on..
Walkers can take the coastal 5K course at East Hampton Main Beach, 101 Ocean Ave, following a beachside route alongside the running races. A virtual option runs 9/27 to 10/4 allowing walks on track, treadmill or elsewhere with online time uploads..
October 2026
The Memorial Walk at Bluff Point State Park offers a 2 mile course for walkers, held rain or shine. Registration carries a $30 fee and includes an event t shirt; the walk takes place alongside a Kids' Fun Run.
The Madison Memorial Walk is a 2 Miles route at Hammonasset State Park, 1288 Boston Post Road, Madison CT, following park paths. The walk runs alongside the event's running races and supports community programs for grieving children and families.
Walkers can choose the 3.1 Miles course or the kids 0.5 Miles fun run; strollers are allowed. The off road mostly flat course at Hallock State Park passes beaches, vineyards, ponds and forests with sections of loose gravel and grass.
Walk the scenic 5K course from 5 Indian Neck Avenue in Branford, CT, along water views and autumn scenery. Finish line treats include a freshly baked cider donut and a beverage from New England Brewing Company for those 21 and over with valid ID..
November 2026
A casual 2 Mile walk at the Branford Thanksgiving 5K event starting at Walsh Intermediate School, designed for all ages and abilities. The event uses a flat, scenic course through Route 146 and Pine Orchard Golf Course and includes pre and post r..
March 2027
Chip timed 5k on a two lap loop around Osprey's Dominion Vineyards in Peconic NY on cross country style terrain suitable for walkers. Walking is allowed; strollers are permitted but not recommended due to uneven ground.
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.