Guilford
Walking Events Calendar near Guilford 2026-2027
Monthly updates for Guilford
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Explore the top walking events near Guilford for 2026-2027! We've gathered 60 great walks in the area. Check out our detailed list below to find your next local walk.
November 2026
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.
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
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
March 2027
Chip timed 5k on a two lap loop around Osprey's Dominion Vineyards in Peconic NY on cross country style terrain suitable for walkers. Walking is allowed; strollers are permitted but not recommended due to uneven ground.
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
Walkers follow the 5K course starting on Water Street in Sag Harbor, mostly flat with a few gentle hills and finishing adjacent to the harbor, with participant tee shirts and refreshments.
May 2027
Walkers can choose an untimed John May Mile fitness walk or the 5K across the Peconic Landing campus in Greenport, NY. Strollers, baby joggers, rollerblades, skates and pets are not permitted on the course.
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.
Walkers can do a 5K course starting at Greenport High School on Front Street in Greenport, with on course water stations, restrooms and free finish line photos alongside the run.
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.
Walkers can choose the 10 km or 5 km routes on a scenic Shelter Island course starting at Shelter Island Union Free School District, 33 N Ferry Road. Routes include water stops, a ferry shuttle between ferries and the race site, and a staffed..
July 2027
Walkers can choose 5K or a 1 Mile course starting at Miller Avenue School in Shoreham, with a mapped route online and water and fruit at the finish. The 5K offers live results and free finish line photos, and personalized bibs if register..