Trumbull
Walking Events Calendar near Trumbull 2026-2027
Monthly updates for Trumbull
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Trumbull for 2026-2027! We've gathered 95 great walks in the area. Check out our detailed list below to find your next local walk.
November 2026
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..
The event offers walkers a 5K along the flat Savin Rock boardwalk by the beach, with coastal breezes, no cars, rain or shine; tech shirts and free finish line photos.
Walkers follow the 5K road loop starting at Bethel Municipal Center in downtown Bethel, with a moderately uphill first half and a downhill second half on neighborhood streets.
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..
The event features a 1 Mile untimed walk and a 5K run walk from Rotary Club of Orange, 525 Orange Center Rd, on a scenic certified course with one water stop and nearby bathrooms.
Walkers are welcome on the 5K run walk at Nissequogue River State Park, Kings Park NY, with an untimed 1K kids trot; walkers wheelchairs and strollers should start at the back for safety.
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 do the 5K from 2900 Purchase Street in Purchase NY alongside the running races; participants 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 have up to 6 hours on the 2.3 miles loop at Roosevelt Forest, Stratford CT, on roots, rocks and rolling hills with a pavilion aid station, lap chip and food.
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..