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Walking Events Calendar near Brookline 2026-2027

Monthly updates for Brookline

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Brookline for 2026-2027! We've gathered 89 great walks in the area. Check out our detailed list below to find your next local walk.

November 2026
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.
December 2026
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.
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.
Walkers can choose a 5K or 1 Mile route on trails in Wompatuck State Park, Hingham, starting from the DCR Wompatuck State Park Visitors Center. There is a short 5+ minute walk from the Visitors Center to the trail start; dogs are not allowed..
Walkers can choose a 1 Loop Walk or a 1 Mile Walk at Franklin Park Playstead in Boston, MA. The course is 99% grass and dirt through the Frederick Law Olmstead Emerald Necklace park system and runs alongside the event races.
July 2027
Walk options include 2.5 miles and 5 miles on a road course starting at N. Attleborough Middle School, N. Attleborough, MA. The course provides water stops (1 for the 2.5, 3 for the 5), finish line photos, snacks and bands along the route.
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