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Walking Events Calendar near Swampscott 2026-2027

Monthly updates for Swampscott

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Explore the top walking events near Swampscott for 2026-2027! We've gathered 87 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
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 5K or Half Marathon, start and finish at Cashman Park, Newburyport, on flat coastal roads and Clipper Trail, with aid stations and a 1h15 5K limit.
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.
Walkers follow the 5 km course from 48 Geremonty Dr in Salem, NH, with family and leashed, vaccinated dogs welcome alongside runners. Children 12 and under must be accompanied by a parent or guardian, and costumes are encouraged.
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..
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.
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..
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..
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.
Walkers follow a flat 5K route along the Salisbury Ghost Trail, starting and ending at the trailhead off Rabbit Road in Salisbury, MA. Day of registration is available and before and after race festivities are at Winner's Circle Sports Bar.
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 choose the 5K or 5 mile course starting in Shawsheen Square in Andover, with an assigned lane at the start for safety and strollers are allowed.
December 2026
Walkers can use the 5K or Half Marathon courses from the NECC campus in Haverhill MA on rural roads beside the Merrimack River with aid stations and toilets.
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..
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