Southampton
Walking Events Calendar near Southampton 2026-2027
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Explore the top walking events near Southampton for 2026-2027! We've gathered 30 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Certified 5K walk from Pierson Middle High School through scenic Sag Harbor past the harbor and over the Veterans' Memorial Bridge; marina water stop and nearby parking.
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.
The 5K walk starts and finishes at Southampton Intermediate School on local roads through Southampton, with in person bib pick up from 7:30 AM and parking in school lots.
Walkers can choose 5K from Jamesport Town Beach or 10K from Iron Pier Beach, routes through South Jamesport past farms, vineyards and orchards with water stops every mile.
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 can use the scenic 5K route that starts and finishes at VFW Post 414 on Main Street, winding through neighborhood streets and stretching toward Moriches Bay. The course welcomes walkers alongside the running race and accommodates stroller..
Walkers can choose 5K or 10K, begin at Warner's Park via bus from Hampton Bays Middle School, on a mostly flat coastal course with Ponquogue Bridge and ocean views; bib pickup at the school.
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
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 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..
Walkers can complete the 5K course at the Race Site parking lot behind Turkuaz Grill in Riverhead NY; in person and virtual entries offer bib pickup and photos.
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.
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.
April 2027
Walkers follow the 5K course starting on Water Street in Sag Harbor, mostly flat with a few gentle hills and finishing adjacent to the harbor, with participant tee shirts and refreshments.
May 2027
Walkers follow a 3.1 miles course from Cooper's Beach through local lanes in Southampton, with water stations on course; strollers at back, no dogs or bikes.
Walkers can take the 5K route along Main Beach in East Hampton on a beachside course with free parking, refreshments and free finish photos; no dogs allowed and strollers should start at the back.
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.