Fairfield
Walking Events Calendar near Fairfield 2026-2027
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Explore the top walking events near Fairfield for 2026-2027! We've gathered 114 great walks in the area. Check out our detailed list below to find your next local walk.
September 2026
The event offers walkers a 1 mile Run Walk at Mill Dam Park in Halesite, and a 5K ruck option that involves walking with a weighted rucksack alongside the running races. It welcomes participants of all ages and fitness levels.
Walk the 5K course at FDR State Park Lot 1, 2957 Crompond Road in Yorktown Heights in a park setting alongside the running races. Race day registration is available and festivities include vendors, food trucks, live music and pet adoptions.
Walkers can join the certified 5K course at Fairfield Hills, 3 Primrose St, Newtown, CT, on event day. Entry is $30 plus three canned goods for the main walk and $5 plus three canned goods for the kids walk, held alongside the running races.
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.
Walkers may choose the 5K or the kids 1/4M Fun Run at Belmont Lake State Park, Serene Picnics and Recreation on the Water in West Babylon, NY. Baby strollers and baby joggers are permitted on the course and finish line photos are free.
Walkers can complete one or more 3.1 mile loops on a fully accessible course at Heckscher State Park from Taylor Pavilion Field 2, with options from a short 5k up to 26.2 miles. The event offers adaptive changing tents, family activities..
Walkers can complete the 5K course at East Islip Marina Park or use the virtual 5K option, with a free kids fun run alongside the races. Registrants receive a dry fit T shirt if registered early, plus free finish line photos, live results and..
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 can complete a 5K in person at St Francis Episcopal Church, 2810 Long Ridge Rd, Stamford CT, on a USATF certified course with canine companions welcome. A virtual 5K is available Sept 14 to 20 for remote participation.
Walkers can choose a 2 km Fun Run/Walk in Northport starting at William J Brosnan School, with shuttle service from Northport High School to the start. Water is available at the start and on course, split clocks at every mile, and a 10 km vir..
Walkers participate in the Brain Aneurysm Foundation Long Island Run/Walk at Jones Beach State Park on Long Island. The event includes a walking option alongside the running races and supports brain aneurysm awareness and fundraising.
Walkers follow the 5K course starting at Jeffrey Lane and Main Street by the Setauket Fire Department. Parking is at Setauket Elementary School and bib pickup is at the fire department with early pickup on 9/18 in the evening.
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..
The event offers walkers a scenic loop along Pear Tree Point Beach in Darien with options for 1.5 Miles or 5 Miles, alongside the running races. Parking is limited so carpooling, biking, or walking is encouraged, family friendly activities ar..
Walkers can join a 5K course at Sherwood Island State Park in Westport alongside the running races. No dogs or alcohol are permitted and there is no on-site registration; children 9 and under register free and family pricing is offered.
Walkers follow a 5K scenic, pet friendly route at Belmont Lake State Park with a light breakfast and photo ops. Raffle entries are available for donated non perishable pet or human food and shirts are first come first served.
The event offers a 5K scenic Middlebury route starting and finishing at Pies & Pub, 1 Store Road, Middlebury CT. The family friendly course is chip timed, provides free pizza for all finishers and free beer for 21 plus, with parking at Meadowview P..
Walkers complete the 5K course starting at Farmingdale High School in Farmingdale, NY, alongside the running race. Registrants receive a T Shirt and finisher medal, may get a personalized bib if registered three weeks ahead, and get free finish l..
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.