Massachusetts
Massachusetts Walking Events Calendar 2026-2027
Monthly updates for Massachusetts
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Explore the best walking events in Massachusetts for 2026-2027! Our updated list features 166 great walks across the region. Find your next walk in Massachusetts below and join the walking community at these great events!
October 2026
Walkers can choose a 3.1 Miles trail walk through Stanley Park or the wheel friendly 1 Miles Stroll & Roll along accessible park pathways. T shirts are included for those registered by September 18, 2026.
Walkers can take part in the live in person 3.1 Miles (5K) course starting at Barnes Memorial Park in Dedham, MA. The park route is part of a community event with food, drink and music alongside the running races and supports the Dedham Education..
Walkers can take part in the 5k either in person or virtually alongside running races, with a free Kid's Dash for ages 8 and under. The event raises funds for the Patient and Caregiver Fund to support patients and families.
The event offers a 5K fitness walk as two laps of a 1.55 mile loop in Highland Park, Attleboro MA, starting at 104 Mechanic Street. The traffic free course is on wide grass paths with short compact crushed stone sections and pre registered walker..
Walkers use the 1.5 Miles walking only route around Ashley Reservoir in Holyoke, with day of activities at the Holyoke Elks and held alongside a 5k run. Registration opens 6/1/2026, fee $30, and proceeds benefit YWCA survivor services.
The event offers a 1 km Walk/Roll starting at 91 Mill Street in Dracut, MA. The route runs alongside the 5K run and supports fundraising for people living with MS in New England.
Walkers follow a 5K route starting at Chesterwood, 4 Williamsville Rd, Stockbridge MA, alongside the running races. The event offers refreshments and awards and carries a $35 entry fee.
Walkers can take the 5K course starting at the Knights of Columbus on Nichols Street, following Nichols, Willett Parkway, Westover Parkway, Rugby, Albemarle, Essex and Croydon back to Nichols Street. The route has at least one water station and p..
Walkers can join the 5K Fun Walk at The GazBar Sports Grill, 1045 Central Street, Leominster, MA. Day of onsite registration is available, walkers receive event swag and food with registration, children under 10 are free with a registered adult a..
Walkers will follow a route on Boston Common alongside the 5K run and can enjoy a resource fair, family activities and entertainment around the park. The walk is part of a fundraising event supporting autism research, advocacy and community resources..
Walkers can choose a 5K along the traditional Homecoming route beginning and ending at Lynch Park in Beverly or a shorter half mile fun run for younger participants. Walking and strollers are encouraged and the event is open to everyone; no d..
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 do the in person or virtual 5K from 120 Main Street in Buzzards Bay, with parking at the Buzzards Bay Recreation Area lot. The in person USATF course has professional chip timing and bib pickup a few steps down the road at 120 Main St..
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.
Walkers can take part in a 5K walk starting at 4107 Main Street in Palmer, MA alongside the 5K run. The event supports Palmer High School students traveling to Washington, D.C., and the first 200 registrants receive a T shirt.
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.