Fairfield
Walking Events Calendar near Fairfield 2026-2027
Monthly updates for Fairfield
Get new running races (and updates) in your inbox every month.
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.
November 2026
The event offers a 5K road loop that starts at Bethel Municipal Center in downtown Bethel and goes through the town neighborhoods. The course is moderately uphill in the first half and downhill in the second half, with the first and last one thir..
Walkers can complete the 5K course starting at 575 Vanderbilt Parkway, Dix Hills, NY 11746, with on site parking and extra nearby parking. Water, bathrooms and free finish line photos are provided, and walkers can get a personalized bib if regist..
A casual 2 Mile walk at the Branford Thanksgiving 5K event starting at Walsh Intermediate School, designed for all ages and abilities. The event uses a flat, scenic course through Route 146 and Pine Orchard Golf Course and includes pre and post r..
December 2026
Walkers can join the 3.1 Miles course alongside the running races, starting at 370 Bassett Road, North Haven, CT. Walkers receive a shirt, jingle bells, and a medal.
Walkers can complete the 5K out and back course starting at 10 Washington Parkway in Stratford along a flat scenic waterfront in the Lordship section. The family friendly route suits all abilities and collects new, unwrapped toy donations at bib..
Walkers can complete the 5K on forest trails at Roosevelt Forest, 700 Peters Lane, Stratford CT, following an off road wooded route that requires a little trail experience. The pavilion is the sole aid station; parking is limited and larger vehic..
January 2027
March 2027
Walkers can choose 5 km or a 1 mile family walk from Smithtown Elementary School in Smithtown. The relatively flat course runs through residential streets with police control, water stops and mile splits, and bib pickup is available before an..
Walkers follow the 2 Mile Run/Walk on Main St in Patchogue along town streets, with course details available. Packet and bib pickup is at West Ave and Main St by Blue Point Brewery, with suggested parking north of Main St or via Waverly Ave.
April 2027
The 4k Jay Walk offers a 4 km non competitive route starting at the John Jay Middle School field that follows the wooded John Jay Community Trail. It skips the first out and back loop, starts after the 5k runners enter the woods, and finishes at..
Walkers can join the 5K on the walk and bike path at Heckscher State Park in East Islip, with baby strollers and joggers permitted if they line up in the back. Bibs are provided for all and refreshments and post race snacks are available.
Walkers can choose 5K, 10K, or a 4 hour option on the 3.2 mile loop at Lake Mohegan, Fairfield CT. Trails are runnable and varied. Water at start finish for 4 hour and 10K; no on course aid for 5K and event is cupless.
May 2027
Walkers can follow the 5K course starting at The Mary Louis Academy in Queens, with a mapped route available online. Amenities for walkers include free finish line photos, live, text and email results, and in person or virtual bib pickup with per..