Boston
Walking Events Calendar near Boston 2026-2027
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Explore the top walking events near Boston for 2026-2027! We've gathered 83 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
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
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 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 non competitive 2 Miles walk over the hilly Mount Hood Golf Club area, starting 0.2 miles from the Melrose Fish & Game Club. It is an easier festive option alongside the races, with parking near the clubhouse so participants should expect a sho..
Walkers follow the 5K route that starts and finishes in Davis Square, Somerville, winding through the streets and squares of the city. The event includes a post race party in several local bars.
April 2027
Walkers can take part in a 5K walk starting at 137 Monument St, Haverhill MA on the Hill Thrill road race course. The 5K route is described as great for seasoned runners, avid walkers, or anyone in between and runs alongside the running races.
May 2027
The event offers walkers a community 5K route that starts at 7 Bishop Street in Framingham, MA, alongside the running races. Packet pick-up and race day registration are available, and there is free parking behind 7 Bishop Street.