Massachusetts
Massachusetts Walking Events Calendar 2026-2027
Monthly updates for Massachusetts
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Explore the best walking events in Massachusetts for 2026-2027! Our updated list features 166 great walks across the region. Find your next walk in Massachusetts below and join the walking community at these great events!
September 2026
Live Like Scott at Hampden Memorial Park in Hampden, MA offers a casual fun run or walk on park paths plus a hike option to Goat Rock with a memorial bench overlooking the valley. Walkers join family friendly activities and youth 10 and under are fre..
Walkers can take the 1 Mile walk at Lt. Ross Park in West Peabody on park paths and green space. The walk runs alongside the 5K race and is followed by an after party with live music, food trucks and lawn games.
Walkers can use the 5K course at 82 Wheelock Ave, Millbury, featuring three short hills in the first half, a fast downhill and a flat finish. Start and finish are adjacent to parking and number pick up and registration, and pets on a leash and st..
The event offers a 5K walk starting on Mountain Rd near the Skinner State Park gate with a water stop at the halfway point. The paved route has gentle downhills and a final mile climbing about 800 feet to summit views over the Connecticut River.
Walkers can take part in the 5k (scenic 3.1 mile) route around Sandwich Marina and the beach, starting and finishing at Stop & Shop Plaza, 65 Rt 6A, Sandwich MA. Walkers go alongside the running race; runners leave the start first.
Walkers follow a loop around Crystal Lake starting and ending in the parking lot of Sacred Heart Parish in Newton. The family friendly route is 1.5 Miles and individual registration is $25 which includes one t shirt.
Walkers join a 5M walk with croissants and matcha, held alongside the running race. The paid event supports Asian small businesses and local AAPI nonprofits, has no medals or shirts, and is capped at 100 participants.
Walkers can take the 5 km road course from the Holiday Inn Express at 360 Airport Rd in Fall River and return the same route. Free onsite hotel parking is available, and the event includes a walking option alongside the running race.
Walkers can use the 5K course starting and ending at Moon Hill Brewing Co., Parker Street, Gardner, MA alongside Oktoberfest activities. First beer provided with registration is served after the course and awards honor the top 3 M/W/N walkers.
A community walk around Ashley Reservoir in Holyoke, held at the Elks Club, offers a Fun Walk of ~1.5 miles along reservoir scenery. Walkers receive water, a finisher cider donut and cider at the post event celebration.
Walkers can choose the 1 mile option or join the 5K route, both based at the Williamstown Youth Center, 66 School Street. Daily and occasional walkers, families with pets and strollers are welcome and on site registration is available.
Walkers can follow a family friendly 3.1 mile (5K) route starting near the rear parking lot of Franklin Park Zoo off Pierpont Road, Boston. In person and virtual options welcome all ages; children 5 and under free, with music alongside run.
Walkers can follow the 5K road course beginning at 33 Howard Street in Northborough, MA alongside runners, with bananas and water provided.
A community fundraising walk of 3 Miles along the Assabet River Rail Trail starting at Immaculate Conception Meehan Hall, 119 Washington St., Marlborough. Walkers may complete the full distance or shorter routes, registration is free and extra fo..
Walkers follow the 5K loop starting at Plainridge Park Casino, 301 Washington St., Plainville MA, circling the historic horse track and surrounding casino grounds. Walkers share the course alongside the running races.
Walkers follow a scenic loop to the Scituate Lighthouse from 1 Kent Street in Scituate MA, covering 3.75 Miles. The route offers an option to turn around at the Scituate Community Center for a shorter outing.
Walkers can take part in a family friendly untimed 1 Miles walk from 951 Broadway St, Lowell, MA 01854 through a dog friendly block party with music, food trucks, a beer garden and local vendors. The walk runs alongside a timed 5k run.
Walk a 3.1 Miles 5K route at Smoke Crest Farm and animal sanctuary from 830 Springhill Rd, Barre MA, alongside a community health fair with resource booths and educational presentations. Pre registration is $15 and day of event is $20 for the 5K;..
Walkers follow a 1 mile route in Nantucket starting at 33 Bartlett Farm Road at Bartletts Farm, with bib and t shirt pick up available the day before and on event day. The walk runs alongside the races and offers a virtual option.