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Walking Events Calendar near Deerfield 2026-2027

Monthly updates for Deerfield

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Explore the top walking events near Deerfield for 2026-2027! We've gathered 24 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.
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 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.
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.
September 2026
Walkers follow a 1.5 mile mixed pavement, field and trail course from Littleville Road to the dam flagpole, with the steep DAM hill; bib pickup at Gateway Regional School lot.
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 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..
5K walk starts at Wilmington Police Department, 40 Beaver St, Wilmington VT, following a community 5K course alongside the running races. Registration fee is $30 and the event is family friendly with a kids fun run.
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.
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.
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 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 may take part in the 24 hours or 12 hours events around and near the New Salem Common in New Salem MA.
Walkers can choose the 5k fun hike or the 10k and 25k routes, all on rugged single track trails in Mt. Tom State Park with start parking at Bray Lake. Aid stations are about every 5 miles and an early start is available on request though..
November 2026
Walkers can join the timed 5 km walk starting at Holy Family Roman Catholic Church, 29 Sugarloaf St, S. Deerfield, with parking, restroom and shelter and the same route as runners.
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.
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