Winchendon
Walking Events Calendar near Winchendon 2026-2027
Monthly updates for Winchendon
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Winchendon for 2026-2027! We've gathered 20 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
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.
The untimed 5k fun run hike at Northfield Mountain Recreation Area is on hilly trails with about 900 feet of climbing, aid at 2.1 miles, and no ranked results.
September 2026
Walkers follow the 1 mile inflatable fun course at Butterfield Park, 84 E. River St., Orange MA. The event is a family friendly fundraiser for Fisher Hill School sixth graders, with pre registration and day of registration fees of $15 and $20.
Walkers cover a 2 Miles loop of the bike path from Nash's Mill Road in Greenfield, MA near the river. Entry is $25 until race day and $30 on race day.
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 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 can use the 5K course starting and ending at Moon Hill Brewing Co., Parker Street, Gardner, MA alongside Oktoberfest activities. First beer provided with registration is served after the course and awards honor the top 3 M/W/N walkers.
Walk a 3.1 Miles 5K route at Smoke Crest Farm and animal sanctuary from 830 Springhill Rd, Barre MA, alongside a community health fair with resource booths and educational presentations. Pre registration is $15 and day of event is $20 for the 5K;..
October 2026
Walkers can enjoy a 5K scenic course starting at New Ipswich Congregational Church in New Ipswich NH with peak fall foliage along the route. Registration for the walk is free and walkers who register at least two weeks early receive a free T shirt.
Walkers may choose the 5K route or the kids' 1 Miles fun course, both based at Boys & Girls Club of Souhegan Valley, 56 Mont Vernon Street, Milford NH. Routes take place during the Pumpkin Festival weekend and benefit the club.
Walkers can join the 5K Fun Walk at The GazBar Sports Grill, 1045 Central Street, Leominster, MA. Day of onsite registration is available, walkers receive event swag and food with registration, children under 10 are free with a registered adult a..
Walkers may take part in the 24 hours or 12 hours events around and near the New Salem Common in New Salem MA.
November 2026
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 can join a 5K road walk in Shutesbury starting at 23 West Pelham Road, winding along picturesque town roads and scenic countryside. The walk runs alongside the running races, suits all abilities, and has registration from $30.
The event includes a 3 miles course and a 1 mile kids option on Upper Dummerston Road near Brattleboro Country Club; strollers welcome and the road is open so walkers keep left and watch traffic.