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.
October 2026
Miles for Moriah offers a flat, accessible beach boardwalk walk of 5 Miles, starting and ending at Riva on Beach St. The easy paced route features ocean views and welcomes walkers of all ages and abilities, with on site registration.
5K, 10K and Half Marathon walks start inside Heritage Park in Mount Sinai, NY; the 10K and Half Marathon use the North Shore Rail Trail for much of the route. In person bib pickup begins one hour before and personalized bibs require registr..
Walkers take a scenic shaded 5K trail at Blydenburgh County Park on dirt roads and hard packed trails with a few sandy spots. Bathrooms are nearby, hydration is provided at the finish, and strollers and wagons are not permitted.
Walkers can follow the 5K course starting and finishing at the lower parking lot of Saint Anselm’s Church in Shoreham, partly along the North Shore Rail Trail. In person entries have shirts guaranteed for pre registration by September 14 and a fa..
Walk the 5K on scenic trails at Belmont Lake State Park on a stroller friendly, pet friendly course. Facilities include restrooms, parking and one water station, and walkers can receive a personalized bib if registered three weeks in advance.
Untimed 1.7 mi walk starts at Trumbull High School on the A House driveway near the big lot on a mostly flat route. Strollers and leashed dogs are allowed but dogs must start in back and bring a poop bag; walkers should carry their own water.
Walkers can take part in the USATF certified 5K course through Patchogue starting at Shortfront Park, 49 Smith Street. The event offers in person and virtual options (virtual 10/24 to 11/1) with water stations and toilet facilities along the cour..
Walkers can take part in a family 5K walk at 1 Heckscher State Pkwy in East Islip NY. A virtual 5K option is offered alongside the run and proceeds support service dog programs for veterans, first responders and rescue animals.
Walkers can choose in person or virtual 5K on the USATF certified course at Heckscher State Park FIELD 1 in East Islip. In person walkers have bib pickup from event staff one hour before the event and free finish line photos; personalized bibs if r..
The 1 Mile Fun Walk starts at the Farmington Canal parking lot on Sherman Ave in Hamden, CT. The walk takes place alongside the event's 5K and 10K running races.
Walkers may follow the 3.1 mile course or the shorter 1.7 mile route from Mineola Lake through scenic cemetery paths with lakes and fall foliage. Water stations and restrooms are provided and the course is stroller and dog friendly.
Walk the scenic 5K course from 5 Indian Neck Avenue in Branford, CT, along water views and autumn scenery. Finish line treats include a freshly baked cider donut and a beverage from New England Brewing Company for those 21 and over with valid ID..
November 2026
At Tarrywile Park in Danbury walkers can choose 10K, Half Marathon, or Marathon on a looped, technical single track with close to 3K elevation and lakes and viewpoints. Aid stations are on course but walkers must carry their own cup or bo..
Walkers are welcome on the 13.1 miles trail at Roosevelt Forest, 700 Peters Lane, Stratford CT, consisting of eight 1.64 mile wooded loops on marked singletrack and doubletrack with roots, rocks and rolling hills. Aid station and porta potties ar..
Walkers can choose 10 km or 5 km routes at Westchester Community College in Valhalla, NY, with an untimed 5 km option alongside the running races. Both in person and virtual options are offered.