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 the 5k fun hike or the 10k and 25k routes, all on rugged single track trails in Mt. Tom State Park with start parking at Bray Lake. Aid stations are about every 5 miles and an early start is available on request though..
Walkers can choose the 5K course starting at Pierce Beach, following Riverside Avenue along the Taunton River and returning to the beach. Same day registration is available and volunteers will be on course with water and snacks.
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
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..
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 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..
Walkers follow a road 5k course of 3.1 Miles at Polar Park in Worcester, MA, alongside the running races. Same day registration is available and the event welcomes all fitness levels and strollers, with post event food, music and prizes.
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..
Walkers can take the 5K course starting at Buzzards Bay Brewing at 98 Horseneck Road, Westport, MA, held alongside run and ruck options. The event supports Mission 22 and raises funds to help veterans struggling with suicide.
Walkers can join a 5K road walk in Shutesbury starting at 23 West Pelham Road, winding along picturesque town roads and scenic countryside. The walk runs alongside the running races, suits all abilities, and has registration from $30.
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..