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Walking Events Calendar near Sterling 2026-2027

Monthly updates for Sterling

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Explore the top walking events near Sterling for 2026-2027! We've gathered 63 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 follow a muddy 5K at 508 INTL Adventure Sports Center Boston on a course of mud pits, obstacles and slides with mud no deeper than waist and quick dry gear recommended.
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 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.
September 2026
Walkers take the 5 km course at 7 Stadium Drive in Nashua, NH alongside the 5K run. Service member and veteran entries and youth 12 and under are listed as free and event shirts and registration information are available.
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.
A casual 5K walk starting at Mine Falls Park Stellos Stadium Entrance that follows the trails of Mine Falls. Open to all ages and dogs, walkers can go at their own pace alongside the running races.
The event includes a 5K Walk and Roll starting at 78 Boston Rd, North Billerica, MA. The walk takes place alongside the Cool Kids Road Race as part of the NEPC fundraiser.
Mine Falls Park, 7 Stadium Drive, Nashua offers a 3K walking trail and a walking friendly 5K route. Trails run through woods and by the river, with some paved sections but mostly dirt and uneven surfaces, and the course is open to the public..
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 choose the 5K or 1 mile course at Hopkinton State Park on paved, rolling hills; it is fully wheelchair accessible and welcomes strollers, wagons, and wheelchairs.
Walkers can choose the 5K course starting at Mascenic Regional High School, 175 Turnpike Road, New Ipswich NH. The walk is offered alongside the running races as part of the MRHS Homecoming community celebration.
Walkers can do the 5K course starting at 82 Wheelock Ave, with three short hills early, a downhill and flat finish; start area adjacent to parking, pets and strollers welcome.
Walkers can choose 5 km or 1 mile, both start and finish at Fay Park, 20 Foster St, Littleton, on roads closed to traffic with a water stop at the 2 mile mark.
Walkers follow the 5K muddy obstacle course at Carter & Stevens Farm in Barre MA with 18+ obstacles; event is women only and open to ages 7 and up.
Walkers follow a loop around Crystal Lake starting and ending in the parking lot of Sacred Heart Parish in Newton. The family friendly route is 1.5 Miles and individual registration is $25 which includes one t shirt.
Walkers can join the 5K at Moon Hill Brewing Co in Gardner, starting and ending there, with awards for top 3 walkers and a first beer after the event.
Walkers can follow the 5K road course beginning at 33 Howard Street in Northborough, MA alongside runners, with bananas and water provided.
A community fundraising walk of 3 Miles along the Assabet River Rail Trail starting at Immaculate Conception Meehan Hall, 119 Washington St., Marlborough. Walkers may complete the full distance or shorter routes, registration is free and extra fo..
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