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Walking Events Calendar near Chelmsford 2026-2027

Monthly updates for Chelmsford

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

Explore the top walking events near Chelmsford for 2026-2027! We've gathered 105 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
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..
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 can use the downtown course starting at Veterans Park in Manchester on 26.2 miles, 13.1 miles or 5k, with aid stations about every 2 miles and gear check.
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 5K two loop course through Windham Woods School trails at 39 Roulston Road, Windham, with thin uneven trails not accessible to strollers.
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 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 follow a certified 5K course starting at Galliens Town Beach on Beaver Lake, Derry (39 Pond Road), looping residential roads with scenic lake vistas. Packet pickup is available the Sunday and Wednesday before the event and post race hydra..
Walkers can choose the 5K or 5 mile courses from Shawsheen Square in Andover, with an assigned start lane and stroller friendly route alongside running races.
Walkers have 2 miles and 5 miles options on Shrewsbury Common, alongside the running races.
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..
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.
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