Chelmsford
Walking Events Calendar near Chelmsford 2026-2027
Monthly updates for Chelmsford
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Explore the top walking events near Chelmsford for 2026-2027! We've gathered 104 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
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..
August 2026
Walkers on the certified 5k (3.1 mile) loop start at Stark and Elm Streets through downtown Manchester via Elm, Thayer, River and Canal, with a water stop at 1.4 miles.
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.
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 follow a scenic 5K (3.1 miles) course at Horn Pond from the Lake Street parking lot by the Woburn Water Pumping Station. Registrants by July 28 receive an event t shirt and the walk runs alongside the running race.
Walkers can take part in the 5K at Jamaica Pond, 507 Jamaicaway, Jamaica Plain, MA, or join the virtual option. It welcomes walkers alongside running races and promotes community health and social justice.
Walkers at 41 Mile Hill Road Westminster MA can choose 7, 14, 21 or 28 Miles on well marked summit trails of rocky climbs, ski slopes and wooded single track, timed with 10 hours to finish.
Walkers can choose 5 km or 8 km routes through downtown Salem near 283R Derby St alongside the running races. Early bib pick up is available at Marathon Sports, 9 Paradise Rd, to reduce race day lines and ordered shirts or medals are given wi..
September 2026
The event offers a 5k course starting at Daoulas School Complex, 1580 Lakeview Ave, Dracut, on public roadways. Bib pickup and registration are at Harmony Hall, 1660 Lakeview Ave, with pickup Friday 4 to 7 PM and Saturday after 8 AM.
Walkers can follow the 5K course starting at Castle Island in Boston near 2010 William J Day Blvd, with packet pickup available the day before and on event morning. Strollers and wheelchairs are permitted, water is provided at the start and finis..