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Walking Events Calendar near Keene 2026-2027

Monthly updates for Keene

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Explore the top walking events near Keene for 2026-2027! We've gathered 14 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
Walkers follow a 5K course starting and ending at the Keene Family YMCA at 200 Summit Road in Keene. A water station at the halfway point and stroller access with a $10 stroller fee support walkers, and prizes are awarded by age division.
Walkers can choose a 3.1 Miles loop or a free 440 Yards fun route from the playground on Page Road over paved and gravel roads and grass paths with Mount Monadnock views.
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.
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.
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 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.
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 take part in the 24 hours or 12 hours events around and near the New Salem Common in New Salem MA.
November 2026
Walkers can choose a 5K on the flat, fast 3.1 mile Keene Bike Path course through east Keene neighborhoods or a shorter 1 Mile fun walk also on the bike path. The event starts at 93 Railroad St in Keene, NH and offers wheelchair and adaptive..
Walkers take a 4 Miles route starting at Keene Recreation Center (312 Washington Street), following a mostly paved sidewalk course through downtown Keene. Strollers are welcome and no dogs are allowed.
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.
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