Dedham
Walking Events Calendar near Dedham 2026-2027
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Explore the top walking events near Dedham for 2026-2027! We've gathered 92 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
Walkers take part in the Miles for Mary 5K on a scenic course starting at 105 Ocean Ave, Marblehead, MA, held alongside the running race. The event raises funds and awareness for brain cancer research in memory of community members.
Walkers follow an out and back lap on Mansfield's WWII Veterans Memorial Trail of at least 2 1/2 miles over paved, gravel and grass. Laps are done within a 6 hour time limit and carried pack weight is measured at the start and finish of each lap..
Walkers can join a family walk of 5K around Lake Quannapowitt, starting at 1 Church Street Lower Common, Wakefield. The mostly flat fall loop suits families and runs alongside the running races and benefits Woodville Elementary School.
Walkers can choose an untimed 5K or 1 mile Memorial Walk starting at 90 Stow Street, Concord, MA, benefiting Rachel's Gift. The event is untimed and includes a virtual option.
In person walkers follow course maps for the 1.5 Mile Walk starting at Mitchell Elementary School, 187 Brookline St, Needham MA. A virtual option lets walkers complete the 1.5 Mile Walk anywhere during the October 16 to 18 weekend on trails,..
Walkers follow a 5K route of two clockwise loops around Jamaica Pond, starting at the Jamaica Pond Boathouse in Jamaica Plain. The course uses Emerald Necklace pathways and is accessible by transit, on foot or by bike with nearby parking.
Walkers follow a 5K course at Fiedler Field, Charles River Esplanade, on paved paths with some cobblestone footbridges. The walk is untimed with an unchipped bib; strollers and leashed dogs are allowed and ADA portable restrooms are onsite.
Walkers can choose a 3.1 Miles out and back course or a 1 Miles loop, both starting and finishing at Ashland Middle School. Routes pass open fields, wooded nature trails and paved paths with a grassy school campus option for a gentler route.
Walkers can follow the 3.1 Miles route through Artesani Park in Brighton, MA alongside running participants. The community event raises awareness and supports lupus education, advocacy, research, and patient support.
November 2026
The event offers a 5 km walk on a flat road course starting and finishing at Mullein Hill, 25 Staples Shore Rd in Lakeville, following local residential streets. Water, fruit, granola bars and juice are provided and free onsite parking is availab..
A measured 5K road walk alongside the 5K race, starting near the Walpole Public Library and centered on the Walpole Italian American Club. The course runs on town streets; no street parking on the course, use Knights of Columbus or nearby town lo..
Walkers can choose a 1.4 mile walk with 5k and 10k events alongside, all based at Curtis Middle School, 22 Pratts Mill Road, Sudbury MA. Same day registration and pre race bib pickup are available, and strollers and special needs particip..
The 5K starts at Canton High School Memorial Field, climbs to the upper campus past the tennis courts and returns via neighborhood streets to the football field. Restrooms are at start and finish and parking is at Canton High lots.