Chesterfield
Walking Events Calendar near Chesterfield 2026-2027
Monthly updates for Chesterfield
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Explore the top walking events near Chesterfield for 2026-2027! We've gathered 14 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Guided uphill hike up Stratton Mountain covering 2.14 Miles from base to summit through scenic mountain terrain, followed by a gondola ride down. Participants meet at the main base area in South Londonderry; moderate effort and advance sign up is..
August 2026
Walkers can choose 3 km or 8 km routes starting and finishing in downtown Shelburne Falls, MA on mostly scenic rolling paved roads.
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 can join the 5K (3.1 miles) Springfield Dam Run at the Army Corps of Engineers property on 98 Reservoir Road in Springfield VT. The course follows trails and dirt road with slight elevation gain, fast downhills and views of Mt. Ascutney.
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.
October 2026
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
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.