Winchester
Walking Events Calendar near Winchester 2026-2027
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Explore the top walking events near Winchester for 2026-2027! We've gathered 7 great walks in the area. Check out our detailed list below to find your next local walk.
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.
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 the 3.1 Miles Run/Walk course that starts and finishes on the track at Martinsburg High School’s Cobourn Field. The route runs down Bulldog Blvd, crosses Queen Street and includes roughly 2.5 miles out and back on the Frog Holl..
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.
October 2026
Walkers can use a 5K route at Spring Mills High School and Dupont Soccer Complex in Martinsburg. Walkers and strollers are welcome; parking is at the high school, campus roads close for participant safety, and 5K entries include a T shirt.
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..