Chester
Walking Events Calendar near Chester 2026-2027
Monthly updates for Chester
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Explore the top walking events near Chester 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
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 take the 2 Mile route through the Fitzgerald Cornfield at 112 Beecher Road, Woodbridge CT, with ample parking at the Cornfield lot, Beecher Road and Meetinghouse Lane. Refreshments, a verified time, awards and event t shirts are provi..
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.
September 2026
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.
The Memorial Walk is a 2 mile route at Winding Trails in Farmington along Memory Lane, held alongside a Kids' Fun Run. Walkers can expect a family friendly route with activities and optional custom memorial signs.
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 choose the 2 Miles Family Fitness Walk starting at 360 Amity Road on the JCC campus, with a course winding through Woodbridge residential neighborhoods. Free on site babysitting for children ages 2 to 8 is available during the races and..
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 complete the 5K course starting at Multisports Academy, 109 Sanford St Unit G, Hamden CT, alongside the running race.
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.