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Walking Events Calendar near Weymouth 2026-2027

Monthly updates for Weymouth

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Explore the top walking events near Weymouth for 2026-2027! We've gathered 85 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
The event offers an untimed, unscored abbreviated 1.5 Miles walk at Memorial Field at Natick High School, the designated option for walkers.
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 3.1 miles or 1.2 miles road walks from Lexington High School, with off site parking and free shuttle from Minuteman High School; virtual walk option.
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.
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 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 walk starts at Canton High School Memorial Field on a mixed campus and neighborhood route with hills; restrooms are at start and finish and parking is in school lots.
The event features an in person 5K walk at Endicott Estate, East Street, Dedham MA; strollers welcome, walkers are not chip timed and a virtual 5K option is available.
Walkers can use the 5K course that starts at Plymouth Rock Pilgrim Memorial State Park on Water Street in Plymouth; there are no water stops on course and water is available at the finish.
December 2026
Walkers can complete the 5K course starting at 15 West Street, Natick, MA, on a USATF certified route, with music, vendors, packet pickup at Morse Tavern, and awards.
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..
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