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Walking Events Calendar near Wading River 2026-2027

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Explore the top walking events near Wading River for 2026-2027! We've gathered 92 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
Community run walk offering a 5K course starting and finishing at Suffolk County Police Headquarters in Yaphank. Walkers are supported with water, bagels and fruit, bib pickup from event staff, and T shirts guaranteed if registered by 8/21.
Walkers can choose a 5K course or a 1K kids fun walk at Heckscher State Park Field 4 in East Islip, NY. Amenities for walkers include free finish line photos, personalized bibs if registered three weeks in advance, and a virtual 5K option wit..
The 24K (15 miles) walk starts and ends at Jennings Beach in Fairfield, with options to do one 5 mile lap, two laps, or the full beachside loop. Participants pay a registration fee and are asked to raise a minimum of $300.
Walkers follow a 2K route through Stony Brook Village from 61 Main Street, along rolling hills, tree lined streets and the village harbor. Registration with bib and shirt pickup is at the Reboli Center for the Arts, 64 Main Street.
Walkers can take part in the 5K walk starting at Off the Bay at 220 N Main St in Sayville. After the race there are refreshments, raffles and medals for category winners and the event is rain or shine.
Miles for Moriah offers a flat, accessible beach boardwalk walk of 5 Miles, starting and ending at Riva on Beach St. The easy paced route features ocean views and welcomes walkers of all ages and abilities, with on site registration.
5K, 10K and Half Marathon walks start inside Heritage Park in Mount Sinai, NY; the 10K and Half Marathon use the North Shore Rail Trail for much of the route. In person bib pickup begins one hour before and personalized bibs require registr..
Walkers take a scenic shaded 5K trail at Blydenburgh County Park on dirt roads and hard packed trails with a few sandy spots. Bathrooms are nearby, hydration is provided at the finish, and strollers and wagons are not permitted.
Walkers can follow the 5K course starting and finishing at the lower parking lot of Saint Anselm’s Church in Shoreham, partly along the North Shore Rail Trail. In person entries have shirts guaranteed for pre registration by September 14 and a fa..
Untimed 1.7 mi walk starts at Trumbull High School on the A House driveway near the big lot on a mostly flat route. Strollers and leashed dogs are allowed but dogs must start in back and bring a poop bag; walkers should carry their own water.
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 take part in the USATF certified 5K course through Patchogue starting at Shortfront Park, 49 Smith Street. The event offers in person and virtual options (virtual 10/24 to 11/1) with water stations and toilet facilities along the cour..
Walkers follow a 5K course through the Griffin Hospital neighborhood, starting at 350 Seymour Avenue in Derby, CT. The non competitive, family friendly event offers same day registration and includes a race t shirt for participants.
Walkers can take part in a family 5K walk at 1 Heckscher State Pkwy in East Islip NY. A virtual 5K option is offered alongside the run and proceeds support service dog programs for veterans, first responders and rescue animals.
Walkers can choose in person or virtual 5K on the USATF certified course at Heckscher State Park FIELD 1 in East Islip. In person walkers have bib pickup from event staff one hour before the event and free finish line photos; personalized bibs if r..
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
Walkers are welcome on the 13.1 miles trail at Roosevelt Forest, 700 Peters Lane, Stratford CT, consisting of eight 1.64 mile wooded loops on marked singletrack and doubletrack with roots, rocks and rolling hills. Aid station and porta potties ar..
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