Massachusetts
Massachusetts Walking Events Calendar 2026-2027
Monthly updates for Massachusetts
Get new running races (and updates) in your inbox every month.
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!
November 2026
The 5K starts at Canton High School Memorial Field, climbs to the upper campus past the tennis courts and returns via neighborhood streets to the football field. Restrooms are at start and finish and parking is at Canton High 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.
A 5K walk at Endicott Estate on East Street in Dedham includes a virtual option; strollers are welcome and dogs are not allowed. Walkers are not chip timed, and a kids 1/2 mile event for age 9 and under is also offered.
Walkers follow a 5K out and back route from Cushman Park on Green St to Fort Phoenix, passing the marina and a water stop. Bib pickup is at 56 Bridge Street the day before and morning of the event, with police and volunteers staffing crossings.
The event offers walkers a 5K course starting at HP Clough Elementary in Mendon. It welcomes walkers, strollers and baby joggers alongside runners and benefits the Clough PTO.
The event offers a community 5k walk starting at The Dennis Inn on Scarsdale Road in Dennis, MA, on a road course. Parking is at the Dennis Playhouse and the walk is held alongside the 5k run as a community benefit.
December 2026
Walkers may participate in the holiday themed 5K at Bay State Brewing Company in a community event open to all paces and team participation. The route welcomes walkers alongside runners and supports the Arthritis Foundation.
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.
March 2027
Walkers are welcome on the 5K course through Elm Park with start and finish on Park Avenue near Highland Street, held before the St Patrick's Day parade. The finish area includes a beer garden for parade viewing and packet pickup is available bef..
Walkers can join a 2 mile walk starting on Maple Street immediately after the runners depart; the course goes out to the first mile marker, circles back onto Maple Street and finishes at Dwight and Maple. Entertainment on course and a race T shir..
April 2027
Walkers can take part in a 5K walk starting at 137 Monument St, Haverhill MA on the Hill Thrill road race course. The 5K route is described as great for seasoned runners, avid walkers, or anyone in between and runs alongside the running races.
Walkers can choose a 5K loop through scenic West Island or a Kids Mile; the course is flat with a quick downhill start and a challenging uphill finish. Strollers are allowed and parking is available at Hoppy's Landing about a half mile from n..
May 2027
The event offers walkers a community 5K route that starts at 7 Bishop Street in Framingham, MA, alongside the running races. Packet pick-up and race day registration are available, and there is free parking behind 7 Bishop Street.
Walkers can choose 5K or 1.5 Mile run/walk routes starting at 5 Bridge St in Haydenville, MA. Proceeds support local veterans and the first 100 registrants receive an official race T shirt.
Walkers can choose a 5K or 1 Mile route on trails in Wompatuck State Park, Hingham, starting from the DCR Wompatuck State Park Visitors Center. There is a short 5+ minute walk from the Visitors Center to the trail start; dogs are not allowed..