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Walking Events Calendar near Milford 2026-2027

Monthly updates for Milford

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Explore the top walking events near Milford for 2026-2027! We've gathered 116 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
A 5K walk starting and finishing at Newton North High School, with a kids Fun Run of one lap around the school track.
November 2026
Walkers can choose 3.1 miles or 1.2 miles road walks from Lexington High School, with off site parking and free shuttle from Minuteman High School; virtual walk option.
Walkers can choose a 5K or 1 Miles route starting at DCR Fort Independence at Castle Island on a flat course along Castle Island in South Boston. Complimentary entry options are available for veterans and race kits are shipped with a shipping fee..
A community walk of 3.1 Miles that starts at Randolph Intergenerational Community Center, 128 Pleasant Street, Randolph MA. Walkers join the 5K alongside the run in a charity event benefiting the Friendly Food Pantry of Randolph.
Walkers can use the flat, no street crossing 5K course at Artesani Park, 1255 Soldiers Field Road, or join the 5K virtual walk from home; free snacks and swag.
Walk the 5k or 10k courses starting at 84 Antietam Street in Devens, MA, on a course held in support of Veterans and First Responders. Options include a noncompetitive 5k dog walk and ruck options, and walkers may set their own pace along..
Walkers follow a road 5k course of 3.1 Miles at Polar Park in Worcester, MA, alongside the running races. Same day registration is available and the event welcomes all fitness levels and strollers, with post event food, music and prizes.
A walking only 2 Miles route winds through the streets of Raynham from 420 Titicut Road and finishes at the post race celebration. Registration opens 3/21/2026, closes 5/3/2026, and the fee is $15.
Walkers can do a 5K on a USATF certified mostly flat course with slight rolling hills, starting and finishing at La Familia Restaurant, 263 Shears Street, Wrentham.
Walkers follow a 5K route along the Charles River, starting at 1255 Soldiers Field Rd in Brighton, MA. It is a memorial event held alongside the running race.
A measured 5K road walk alongside the 5K race, starting near the Walpole Public Library and centered on the Walpole Italian American Club. The course runs on town streets; no street parking on the course, use Knights of Columbus or nearby town lo..
At Polar Park in Worcester walkers follow the 5K (3.1 miles) accessible course with water stops, designated parking and a required Running Buddy; finishers receive medals.
Walkers can choose a 1.4 mile route starting at Curtis Middle School, 22 Pratts Mill Rd Sudbury MA; strollers are welcome and same day bib pick up is available.
Walkers can cover 3.1 miles on a course starting and finishing at Boston Common, passing Back Bay and Kenmore along Commonwealth Avenue, with a post race party on the Common.
The 5K walk starts at Canton High School Memorial Field on a mixed campus and neighborhood route with hills; restrooms are at start and finish and parking is in school lots.
Walkers may participate in an in person or virtual 5K at Endicott Estate on East Street in Dedham MA; strollers are welcome and walkers are not chip timed.
Walkers are welcome on the 5K course in Pawtucket, RI, with a kids race alongside. Baby strollers must line up at the back for safety and preregistered participants receive t shirts.
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.
Walkers have 2 miles and 5 miles options on Shrewsbury Common, alongside the running races.
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