Bridgewater
Walking Events Calendar near Bridgewater 2026-2027
Monthly updates for Bridgewater
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Explore the top walking events near Bridgewater for 2026-2027! We've gathered 69 great walks in the area. Check out our detailed list below to find your next local walk.
December 2026
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
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..
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..
May 2027
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.