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!
May 2027
Walkers can choose a 1 Loop Walk or a 1 Mile Walk at Franklin Park Playstead in Boston, MA. The course is 99% grass and dirt through the Frederick Law Olmstead Emerald Necklace park system and runs alongside the event races.
Walkers can join the Family Fun Run/Walk on a flat, smooth 3.1 Miles course along the Northampton Airport tarmac, ideal for steady walking. It runs alongside the running races and offers a family friendly community atmosphere.
Walkers can choose the 5K course that starts and finishes outside Worcester City Hall on Main Street, following a scenic route through Downtown Worcester. A Kids Dash of approximately 1/2 mile is available and strollers must start in the back..
Walkers can take the 5K route starting at Surfside Beach Parking Lot, 4 Western Ave, Nantucket, alongside the running races. Bib pick up is Saturday May 15 at the Police Department from 3:00 P.M. to 6:00 P.M. and Sunday May 16 from 7:00 A.M. to 7..
July 2027
Walk options include 2.5 miles and 5 miles on a road course starting at N. Attleborough Middle School, N. Attleborough, MA. The course provides water stops (1 for the 2.5, 3 for the 5), finish line photos, snacks and bands along the route.