Milford
Walking Events Calendar near Milford 2026-2027
Monthly updates for Milford
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Milford for 2026-2027! We've gathered 85 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
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..
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..
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.
The Madison Memorial Walk is a 2 Miles route at Hammonasset State Park, 1288 Boston Post Road, Madison CT, following park paths. The walk runs alongside the event's running races and supports community programs for grieving children and families.
Walkers take the 4K course from Jimmy Lee Stadium at Crosby High School, on a challenging up, down and flat route around the track and grounds. Parking is in the lots right of the Rotella Magnet School entrance across from the track and packet pick..
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 can choose the 3.1 Miles course or the kids 0.5 Miles fun run; strollers are allowed. The off road mostly flat course at Hallock State Park passes beaches, vineyards, ponds and forests with sections of loose gravel and grass.
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
Walkers can choose a 1 mile walk or join the 5K course starting at Norton School in Cheshire, CT, following the scenic Farmington Canal Line past historic homes. Walkers are not timed; first 550 5K or walk entrants get a long sleeve tech shir..
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..