Old Saybrook
Walking Events Calendar near Old Saybrook 2026-2027
Monthly updates for Old Saybrook
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Explore the top walking events near Old Saybrook for 2026-2027! We've gathered 38 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
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..
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 can complete a 5K at Priam Vineyards in Colchester CT on a well groomed, well marked course through the 40 acre estate and neighboring roads; walkers start behind runners, must register and follow a one hour limit.
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 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.
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 follow a flat, scenic 5K (3.11 miles) boardwalk course starting at Riva on the water, 183 Beach St, West Haven. The route is well marked with volunteers and police, includes one water table, and runs alongside the running races.
A 2 Miles community walk from 1 Palace St in West Haven along the boardwalk with activity stations where walkers use a walk passport to earn raffle tickets. Check in provides a commemorative T Shirt for those registered by August 28 and prepackag..
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 can take the 1 Miles route at Edgewood Park in New Haven on a nicely shaded course ideal for September. Ages 1 to 12 walk free with registration, ages 13 to 18 pay $12 and adults $25, and free lunch is provided to participants.
A 5K (3.1 Miles) route through Hubbard Park in Meriden welcomes casual walkers alongside runners, allows friendly dogs, and supports local nonprofits.
Walkers can take the 1 Miles Fitness Walk on Wheeler High School cross country trails, athletic fields and wooded town recreation areas in North Stonington. On-site check-in is available and family amenities include free child care and tee shirts..
Walkers can complete the 5K course starting at Multisports Academy, 109 Sanford St Unit G, Hamden CT, alongside the running race.
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
Healthy Living 1K walk at 81 S Elm St, Wallingford CT alongside the community road races. Registration is online with advance packet or race morning bib pickup, fee $10 and walk shirts for the first 100 walkers.
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.