Gloucester
Walking Events Calendar near Gloucester 2026-2027
Monthly updates for Gloucester
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Explore the top walking events near Gloucester for 2026-2027! We've gathered 44 great walks in the area. Check out our detailed list below to find your next local walk.
September 2026
Includes a 5K walk from 260 Walden Street, Cambridge, on roads closed for a post race block party with beer garden, food trucks and DJ. Parking is at Danehy Park; number and shirt pick up are available in the days before the event.
October 2026
The event offers an untimed 5K walk along Carson Beach, beginning at DCR Mother's Rest at 125 William J. Day Boulevard in Boston. Walk categories include adult, youth and CRC patient survivor walkers, with day of packet pick up and registration a..
Walkers can choose the 5K distance on the historic cross country course in Franklin Park near Pierpont Rd in Boston. The event welcomes walkers alongside runners and has registration fees ranging from free for BLS students to $30 for others.
Participants walk the 5K at Moakley Park on Columbia Road in Boston with park waterfront views, a water stop near 1.5 mile, two porta potties and a registration tent.
Walkers will follow a route on Boston Common alongside the 5K run and can enjoy a resource fair, family activities and entertainment around the park. The walk is part of a fundraising event supporting autism research, advocacy and community resources..
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 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 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 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.
December 2026
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.