Gloucester
Walking Events Calendar near Gloucester 2026-2027
Monthly updates for Gloucester
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Gloucester for 2026-2027! We've gathered 44 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
August 2026
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.
Competitive walkers follow a 10 km course through Rye NH starting on Central Road near Partners Bank using 211 Central Rd for GPS. Live field limited to 500; cash prizes and limited special T shirts go to top 3 men and top 3 women.
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 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
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..
A 2 Miles fun walk on city streets starts at Leather City Common in Peabody, offered in person or virtually alongside the 5K run. Dogs are welcome for the walk only, must be leashed and there is no charge.
Walkers can join the on site 5K at Lahey Hospital & Medical Center in Burlington MA along the event course alongside the running races. A virtual 5K option lets walkers complete the distance within one week and has a $35 fee.
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 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 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.
The event is a timed 5K walk starting and finishing at Exeter High School at 1 Blue Hawk Drive, Exeter NH. Strollers, handcycles and wheelchairs are welcome; bicycles and dogs are not permitted, and proceeds support families affected by LGMD.
Walkers can use the 5K USATF certified road course that starts and finishes at Burlington High School, 123 Cambridge Street, Burlington MA. Roads remain open with police at intersections, and amenities include a water stop, cider donuts, particip..