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.
September 2026
Walkers can choose a 5K on scenic Ring Road or an untimed 2 Mile walk, both starting at the Campus Center lot at SUNY Old Westbury. The route winds the wooded 603 acre campus past Woodlands Dorms and HorseAbility, and t shirts are provided.
The event offers a 3K walk at Wakeman Boys & Girls Club, Southport, CT, sharing the 5K course for the first half mile before turning south onto Westway. The route is not chip timed, has no awards, and all turns are well marked.
October 2026
Walkers can choose 26.2M 50K 50M 100K or 100 Miles on a 2.5 mile loop at Roosevelt Forest, 700 Peters Lane, Stratford CT, over roots, rocks and rolling hills. The pavilion is the aid station with day and night hydration and snacks and pink..
Walkers can take part in the 5K walk on a USATF certified course through Heckscher State Park in East Islip NY. Amenities include personalized bibs if registered three weeks in advance, bib pickup one hour before the event, free finish line photo..
Walkers can choose the 5K course or an untimed 1 Mile walk at Shorefront Park in Patchogue, NY. A virtual 5K option exists and walkers get free finish line photos; personalized bibs are available if registered 3 weeks ahead.
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 choose a 5K course or a 1K kids fun walk at Heckscher State Park Field 4 in East Islip, NY. Amenities for walkers include free finish line photos, personalized bibs if registered three weeks in advance, and a virtual 5K option wit..
Walkers follow a 2K route through Stony Brook Village from 61 Main Street, along rolling hills, tree lined streets and the village harbor. Registration with bib and shirt pickup is at the Reboli Center for the Arts, 64 Main Street.
Walkers may take part in a certified and timed 5K on Keating Farms Ave in Newtown CT alongside the running races in a family friendly setting. The finish area features adoptable and rescued animal ambassadors and a free post race breakfast, and a..
Walk options include a trail route of 3.1 Miles across scenic farm trails and an accessible flat paved option of 1 Miles. Both take place at Gemstone Farm in Wilton CT and include access to the orchard, lake, trails, an event T shirt, food, b..