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!
July 2026
Walkers can take an untimed 2 Mile route along Carson Beach in South Boston for a relaxed seaside walk. The event is hybrid with in person and virtual participation alongside a professionally timed 5K run.
A 3.1 mile walk or run open to all abilities, held at High Lawn Farm in Lee MA along Laurel Lake. Technical shirts are available to the first 150 registered walkers or runners, and students participate free and get free ice cream at the finish.
Walkers may participate in a professionally timed 5K beginning at the Harbor Hotel Provincetown, 698 Commercial St, and enjoy Provincetown scenery in summer. Registration includes a bib with timing chip, a race shirt while supplies last, and a po..
Walkers follow a 5k out and back from the Herter Park amphitheatre along the Charles River Walk with bridge crossings. Parking, packet pickup at the amphitheatre, and a post event party with free pizza and beverages are available.
The walking only 3 Miles starts at Wixon Middle School on Rt 134 in South Dennis MA. Walkers must walk for prizes or face disqualification. Registration is $25 online, $35 day of, with bib pick up day of only.
Walkers have a mostly flat family friendly 5K route from Upton VFW in Upton, MA, ideal for a family walk before it gets too hot. Day of registration opens at 7am, with a water stop at halfway and parking at the VFW and Rose Garden.
The event welcomes walkers on the 5K course from 175 Lincoln Street in Blackstone MA with race day parking. Strollers start in the back; dogs are not allowed and service animals are permitted with prior arrangement.
Walkers can take part in the full 5K on Martha's Vineyard in West Tisbury, with wheelchair, handcycle and duo team options and a separate 400 m kids fun run. The event starts at 401 Old County Rd and takes place alongside the running races.
Walkers can take part in a 5K course starting at Braintree Town Hall, 1 John F Kennedy Memorial Drive, Braintree MA 02184 alongside the running races. Culturally competent first responder mental health programs will be on site, and race shirts an..
Walkers follow historic trails at Minute Man National Historical Park in Lexington and Lincoln, MA along routes used by Colonial Militia and British forces. The ruck offers a walking option and starts at 210 North Great Road in Lincoln, 22 miles from..
Includes a 1.5 mile walk from Icon Nightclub in Boston alongside a 3 mile run, with participants moving at their own pace. Walkers can expect music, activations like a glitter station and photobooth, check in on arrival, and community support.
August 2026
Walkers can join a 5K route on beautiful Cuttyhunk Island in Gosnold MA, enjoying an outdoor community event alongside the running races. All ages are welcome and proceeds support Cuttyhunk First Aid and Rescue and Cuttyhunk CAN.
Walkers follow the scenic South Boston waterfront on a 5K out and back starting and finishing at DCRs Carson Beach. Two Poland Spring hydration stations are on course; parking is limited and public transportation is encouraged.
Clapp Park, 215 West Housatonic St, Pittsfield hosts an 8 hour event on a certified dirt and cinder track looping .355 mile. The event is walker friendly; walkers may do unlimited laps and trackside aid has bottle drop, no contact refills and persona..
Walkers can choose 1.5 Miles or 3.1 Miles routes from Ryan Playground Neponset Trail, 350 River St, Mattapan. Routes follow the park and Neponset Trail and run with festival and community health fair; T shirts while supplies last.
The event offers walking options 3K and 8K through downtown Shelburne Falls, MA, starting near 75 Bridge St. Registration is required and there is no at the door registration.
Walkers follow a 3 Miles route in downtown Worcester from 64 Franklin Street, passing through the Canal District and downtown streets alongside the official 5K course. The stroller friendly walk is open to all ages; walkers pay $10 and are entere..
Walkers follow a family friendly 3.1 Miles course from South Street across from the Police and Fire Station through hilly and flat sections. Warm ups occur beforehand and parking is at Meetinghouse School and nearby lots.
Walkers can take part in the community Run/Walk covering 5K (3.2 miles), starting at 15 Island Inn Rd, Oak Bluffs, MA. The scenic Martha's Vineyard course welcomes all fitness levels and emphasizes community and wellbeing.
Walkers can complete a 5k along the Spicket River Greenway from 75 Manchester Street in Lawrence, with same day registration and shuttle service available, alongside the running races.