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Walking Events Calendar near Shelton 2026-2027

Monthly updates for Shelton

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Explore the top walking events near Shelton for 2026-2027! We've gathered 81 great walks in the area. Check out our detailed list below to find your next local walk.

November 2026
A road walk of 5K starting and finishing at Redding Community Center on Lonetown Rd (RT 107). This walking only event has a $35 registration fee and registration runs 5/1/2026 to 10/31/2026.
Walkers can choose the dedicated 2.5K fitness walk starting and finishing at Newtown Middle School on routes introduced in 2019. Water and coffee are available; packet pickup is at C.H. Booth Library before the event.
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.
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
The event includes a 2 Miles walk in Milford, CT, held alongside the 5 Mile race. Route and terrain details will be announced later.
March 2027
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..
Walkers complete the 5K (total 3.1 Miles) on campus sidewalks, starting and finishing at the Stony Brook Union Patio and following Circle Road and John S. Toll Drive
Walkers can choose 5K, 10K, or a 4 hour walk on runnable mixed trails at Lake Mohegan, 960 Morehouse Hwy, Fairfield CT, with water at start and finish for 10K and 4 hour.
May 2027
A 3 mile scenic route through the Riverside neighborhood is open to walkers, sharing the course with runners. Bib pickup is at Riverside School.
Walkers may lap a single and double track 2.2 mile loop with roots, rocks, rolling hills and 131 ft gain; pavilion aid and porta potties at 700 Peters Ln Stratford CT.
The untimed Fun Run/Walk of 3.1 Miles follows the Shepaug River through Steep Rock Preserve with a gradual incline. It starts at 2 Tunnel Road, Washington Depot CT; walkers will not receive a race bib.
MS Health Walk is based at Lewisboro Library in South Salem on village and road courses with parking at the library and online course maps, held alongside the race events.
Walkers follow a 5K course in Setauket NY; all 5K walkers receive a shirt and medal. Parking on Washington St, Harrison Ave and Walnut Beach; bib pickup one hour before and personalized bibs for registrations three weeks in advance.
June 2027
Walkers follow an out and back trail beginning and ending at King Road Fire House, crossing Broadway and two intersections, covering 5K with finish line photos and bib pickup.
Walkers follow a 5K course starting on John Street 1000 feet east of Miller Avenue, finishing at bottom of Southgate; bib pickup at Tesla Science Center prev day, race morning.
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