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Walking Events Calendar near Holyoke 2026-2027

Monthly updates for Holyoke

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Explore the top walking events near Holyoke for 2026-2027! We've gathered 27 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
The event offers walking options 3K and 8K through downtown Shelburne Falls, MA, starting near 75 Bridge St. Registration is required and there is no at the door registration.
Walkers use the 5K course from Forest Park Monkey House at 299 Sumner Ave in Springfield, on park paths with vendor areas and a community atmosphere. Registration includes bib and race T shirt plus route and safety info, with parking fees $3 in s..
The event includes a 1 Mile walk that begins at 30 Front Street in Belchertown alongside the 5K community races. Entry is $25 and shirts and medals are guaranteed for registrants until July 25.
The event offers a 5K walk starting at 250 Whitney Ave in Holyoke, with fruit and water provided and a T shirt plus one raffle ticket included with registration. The event is rain or shine and has a $30 registration fee.
The event offers a 5K walk starting at Forest Park near 299 Sumner Ave, Springfield, on accessible park paths with vendors, food trucks and fitness presentations. Registration for the 5K is free and the walk takes place alongside the 5K run.
Walkers take a 5K not timed route based at 60 State Street, Belchertown MA as part of the SOAAR event. Registration is listed and the walking entry fee is $20.
In person walkers can do the 5K of 3.1 Miles in Ellington CT. Course details are pending. Virtual walkers may complete 3.1 Miles, 6.2 Miles or 22.46 Miles anywhere, submit results by email and get packets by mail.
September 2026
Walkers follow a 5K city course from Kenefick Park (Plainfield St.) to 1500 Main St., passing Springfield streets during the parade weekend. Registration options and a commemorative shirt are offered; walkers start separately from runners.
Walkers can take the scenic Norwottuck Rail Trail from Downtown Amherst, MA to Downtown Northampton, MA over 8.1 miles, or join the relay with legs of 5 miles and 3.1 miles. The supported point to point course features live music along th..
The event includes a 5K walk at King Phillips Stockade in Springfield, gathering at the pavilion near the entrance at 70 Columbus Ave. Free parking on site and a family friendly post event gathering with boxed lunch options, music and lawn games.
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.
Live Like Scott at Hampden Memorial Park in Hampden, MA offers a casual fun run or walk on park paths plus a hike option to Goat Rock with a memorial bench overlooking the valley. Walkers join family friendly activities and youth 10 and under are fre..
The event offers a 5K walk starting on Mountain Rd near the Skinner State Park gate with a water stop at the halfway point. The paved route has gentle downhills and a final mile climbing about 800 feet to summit views over the Connecticut River.
A community walk around Ashley Reservoir in Holyoke, held at the Elks Club, offers a Fun Walk of ~1.5 miles along reservoir scenery. Walkers receive water, a finisher cider donut and cider at the post event celebration.
October 2026
Walkers can choose a 3.1 Miles trail walk through Stanley Park or the wheel friendly 1 Miles Stroll & Roll along accessible park pathways. T shirts are included for those registered by September 18, 2026.
Walkers use the 1.5 Miles walking only route around Ashley Reservoir in Holyoke, with day of activities at the Holyoke Elks and held alongside a 5k run. Registration opens 6/1/2026, fee $30, and proceeds benefit YWCA survivor services.
Walkers can enjoy the 4th Annual OAH STRIDES at Simsbury Meadows Performing Arts Center with a 5K route and family festival amenities. The event also features a kids 1 Mile fun run alongside the running races and Family Fun Day activities.
Walkers can take part in a 5K walk starting at 4107 Main Street in Palmer, MA alongside the 5K run. The event supports Palmer High School students traveling to Washington, D.C., and the first 200 registrants receive a T shirt.
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