Woodstock
Walking Events Calendar near Woodstock 2026-2027
Monthly updates for Woodstock
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Explore the top walking events near Woodstock for 2026-2027! We've gathered 7 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
Walkers can choose 5K, 10K, or Half Marathon routes around the scenic Third Winchester Battlefield, starting at 251 First Woods Drive, Winchester VA.
September 2026
Walkers take a 2 Miles loop through the Sherando trail system, starting and finishing beside Sherando Pool in Stephens City. Packet pickup is at Sherando Pool and registration includes a t shirt, bandana and early VIP pool access.
Shenandoah River State Park offers walkers 5 km, 10 km, and half marathon routes. The 5 km is a hilly paved course with 200 ft gain or a flatter trail.
Walkers can do the 5K on a multi surface course on the Laurel Ridge campus, starting at the Student Union Building in Middletown VA. Facilities include refreshments, restrooms and free parking; no pets, strollers or headphones.
Walkers can choose an untimed 1 mile out and back on the paved Sherando Park path, with a course marshal at the turnaround. The walk runs alongside the four mile trail race and starts from the Sherando Park start area in Stephens City, VA.
November 2026
The Thanksgiving Day event offers a walking distance of 3.1 Miles starting at Sherando Park in Stephens City. The course mixes track, pavement, and woodland trails and runs alongside the Kids Fun Run and Tot Trot.
May 2027
The untimed 8 Miles hike starts along the river in Bentonville, VA, with about 600 feet of elevation gain. The route goes through valley and forest with occasional mountain views on mostly smooth single track and some double track and technical s..