New Milford
Walking Events Calendar near New Milford 2026-2027
Monthly updates for New Milford
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Explore the top walking events near New Milford for 2026-2027! We've gathered 49 great walks in the area. Check out our detailed list below to find your next local walk.
November 2026
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.
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..
February 2027
Walkers may register to walk the scenic 7.8 miles loop around glacial Lake Waramaug, starting and finishing at Hopkins Vineyard with lake shore views. The course is mainly flat with gentle rolling hills and a final 0.2 miles ascent up Hopkins..
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..
May 2027
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.