Middlebury
Walking Events Calendar near Middlebury 2026-2027
Monthly updates for Middlebury
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Explore the top walking events near Middlebury for 2026-2027! We've gathered 75 great walks in the area. Check out our detailed list below to find your next local walk.
November 2026
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
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
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.