Berryville
Walking Events Calendar near Berryville 2026-2027
Monthly updates for Berryville
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Explore the top walking events near Berryville for 2026-2027! We've gathered 16 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.
Walkers are welcome on 5K and 10K routes at Leopold's Preserve on Thoroughfare Rd in Broad Run VA; the event is part of a Sippin Series with the Farm Brewery at Broad Run.
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 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.
Walkers can choose 5k or 10k courses starting at Lovettsville Community Park on Milltown Road, Lovettsville, VA; walkers are welcome alongside the running races.
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
Walkers follow the 3.1 Miles out and back course from Grace Episcopal Church in The Plains VA through town to Hopewell Road and return alongside the running race.
Walkers can choose 3k or 6k routes at Barrel Oak Winery and Brewery in Delaplane, VA, on a winery course where walkers and leashed pets are welcome.
Walkers can complete the 5K course around Evandale Elementary and Admiral Richard E Byrd Middle School in Winchester on roads with Race Marshals, water stations, accessible routes and medals.
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.
Walkers are welcome on scenic 5k and 10k routes around Henway Hard Cider on Foggy Bottom Road in Bluemont VA, held alongside the running races.
December 2026
Festive 1 Mile fun walk on the Christian Fellowship Church campus in Ashburn, with holiday market and music; walkers under 12 must be accompanied.
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..