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Walking Events Calendar near Cambridge 2026-2027

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Explore the top walking events near Cambridge for 2026-2027! We've gathered 88 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
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.
Walkers follow the 5 km course from 48 Geremonty Dr in Salem, NH, with family and leashed, vaccinated dogs welcome alongside runners. Children 12 and under must be accompanied by a parent or guardian, and costumes are encouraged.
Walkers can choose a 5K or 1 Miles route starting at DCR Fort Independence at Castle Island on a flat course along Castle Island in South Boston. Complimentary entry options are available for veterans and race kits are shipped with a shipping fee..
A community walk of 3.1 Miles that starts at Randolph Intergenerational Community Center, 128 Pleasant Street, Randolph MA. Walkers join the 5K alongside the run in a charity event benefiting the Friendly Food Pantry of Randolph.
Walk the 5k or 10k courses starting at 84 Antietam Street in Devens, MA, on a course held in support of Veterans and First Responders. Options include a noncompetitive 5k dog walk and ruck options, and walkers may set their own pace along..
A walking only 2 Miles route winds through the streets of Raynham from 420 Titicut Road and finishes at the post race celebration. Registration opens 3/21/2026, closes 5/3/2026, and the fee is $15.
Walkers follow a 5K route along the Charles River, starting at 1255 Soldiers Field Rd in Brighton, MA. It is a memorial event held alongside the running race.
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..
The Community Walk offers a 1.5 Miles route on the high school cross country course at the Academy of Notre Dame in Tyngsboro MA. The walk is held alongside the community runs and requires registration with a $30 fee.
Walkers can take part in the family friendly 5K on a road course starting at Lt. Ross Memorial Park, 32 Johnson Street in Peabody. No strollers or dogs are allowed on the course and post race refreshments are provided.
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.
A 5K walk at Endicott Estate on East Street in Dedham includes a virtual option; strollers are welcome and dogs are not allowed. Walkers are not chip timed, and a kids 1/2 mile event for age 9 and under is also offered.
The event offers walkers a 5K course starting at HP Clough Elementary in Mendon. It welcomes walkers, strollers and baby joggers alongside runners and benefits the Clough PTO.
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