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Walking Events Calendar near Essex 2026-2027

Monthly updates for Essex

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Explore the top walking events near Essex for 2026-2027! We've gathered 63 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
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 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 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.
Walkers can take the 5K on the flat, tree lined Wells Ave loop in Newton, with parking at 1 Wells Avenue and registration at 90 Wells Avenue; strollers and leashed dogs are welcome.
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.
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 take the 3.1 Miles run walk from Dan R. Healy Outdoor Pool in Exeter, NH. The course is fully supported and staffed with chip timing and packet pick up options.
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..
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.
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 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.
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.
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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