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.
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..
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
The 2 Mile walk begins on the Bethlehem Town Green in front of Memorial Hall and follows the 5K course on rolling country roads, turning back at the one mile mark. Parking is at the Bethlehem Fair Grounds with shuttle buses to the Green, and the..
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..
Chip timed 5k on a two lap loop around Osprey's Dominion Vineyards in Peconic NY on cross country style terrain suitable for walkers. Walking is allowed; strollers are permitted but not recommended due to uneven ground.
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 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..
Walkers can choose an untimed John May Mile fitness walk or the 5K across the Peconic Landing campus in Greenport, NY. Strollers, baby joggers, rollerblades, skates and pets are not permitted on the course.