Fairfield
Walking Events Calendar near Fairfield 2026-2027
Monthly updates for Fairfield
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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.
July 2026
Walkers can use the USATF certified 5K course or join the free fun run at Walker Park near Walker Beach in Brightwaters, NY. On site amenities include post race refreshments, a food truck and beer, and a virtual 5K option is available.
Walkers use a mostly flat shoreline course starting at Trubee Doolittle Park on Beach Avenue in Milford. The event is pre registration only, limited to 475 participants, with early packet pickup; Dri Fit shirts for pre registered walkers and refreshm..
Walkers can use the 5K course at Blydenburgh County Park in Hauppauge over pavement, dirt roads and hard packed trails, with parking across the street about a half mile walk to the start. Bathrooms are nearby, informal bag check and hydration at..
Walkers have an untimed 1 mile Holiday Stroll from 10 Washington Pkwy, Stratford, through the scenic, mostly flat Lordship seaside neighborhood. Roads are open so walkers should stay left facing traffic, parking may fill and water tables may not..
An untimed 1 mile walk around scenic & tranquil Twin Brooks Park on an easy course. The walk starts at the same place as the 5K run, has a $30 online registration fee and no paper or cash entries on the day.
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.
Walkers can take part in a 5K health walk that starts at Holy Trinity Orthodox Church on Joe's Hill Rd in Danbury, CT, alongside the running races. Race day registration and check in are at the church and pre registered walkers may receive a T sh..
Walkers can take part in the 5K on a USATF certified course starting at Commack Volunteer Ambulance Corps in Commack NY, rain or shine. Amenities include free finish line photos, personalized bibs if registered three weeks in advance, and T shirt..
Walkers can choose the untimed 1 Mile walk or walk the 3.1 Miles 5K course at Seaside Park in Bridgeport, CT. The 1 Mile is untimed, strollers are welcome, shirts are included for 1 Mile and 5K registrants and advance registration is required..
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 join a 90 minute indoor walk and stair climb at Sacred Heart University Martire Family Arena around the ice rink. Each lap is 0.20 miles with about 80 stairs and 450 steps; a one week virtual 40,000 steps challenge is at participa..
Walkers follow a 4 miles route from Oxhead Elementary School to Hobbs Community Farm: roughly two miles flat, one mile rolling and two climbs. Water and refreshments are at the finish; porta potties are at start and finish.
Walkers use a certified 5k (3.1 Miles) course starting at Pent Rd Recreational Complex in Beacon Falls. Entry fees are $25 for adults and $10 for 16 and under, and the walk takes place alongside the running races.
The event offers a 5K walk starting at The Amber Room Colonnade in Danbury, with a scenic route across the Amber Room grounds. Walkers join alongside the running race and can enjoy a post race barbecue and refreshments on site.
Walkers follow the 5K road course starting and finishing at Islip Terrace Fire Department, 264 Beaver Dam Rd, Islip Terrace, NY, on local streets. Rain or shine, walkers receive a finisher medal, free finish line photos, and personalized bibs if..
Walkers can take part in the 5K run walk through Mill River Park in Stamford, CT, on a park course. Medals are handed out to in person finishers, T shirts are subject to availability after July 17, and the event is rain or shine.
Untimed 1 mile walk at Ronkonkoma Middle School, 501 Peconic St., Ronkonkoma NY. Walkers get free finish photos, shirts if registered before 8/1, and personalized bibs for early registrants; bib pickup opens one hour before the event.
The 5K run/walk follows streets of Glen Cove, starting at Glen Cove High School and finishing near the football field and track. Strollers and joggers are allowed but must line up in the back; bib pickup opens one hour before the event.