Trail Running calendar near Woodstock 2025-2026

West Virginia Trilogy The West Virginia Trilogy is a three-day stage race on and around Spruce Knob, on the Eastern Continental Divide. It takes place over Columbus Day weekend, October 10–12, 2025, and is hosted by the West Virginia Mounta..

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando..

Event details The Full Distance 5k & 10k takes place on October 11 at Locust Shade Park. Points from the event count toward the Year-Long 5k, 10k and Back of the Pack Series and the Sippin Series. A virtual race option is offered. Walke..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. T..

Rocky Gap 25K, 50K, Relay Trail Run The event takes place on Sunday, October 12, 2025 at Rocky Gap State Park in Flintstone, MD (12500 Pleasant Valley Road, Flintstone, MD 21530). The program offers solo and relay entries for two distances..

Event The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series...

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a..

2025 Wilderness Run 5k & 10k The event takes place on October 18 at Wilderness Run Vineyard in Spotsylvania, VA (11109 Plank Rd; GPS 38.325153, -77.719921). It features cross country trail courses with hills. The 5k is an out-and-back o..

Boulder Dash at Pinesburg Quarry is a running event hosted by Martin Marietta in Williamsport, Maryland. It offers a 5 Mile Challenge, a Family Friendly 5K, and a 1 Mile Fun Run for all levels. The 1 Mile Fun Run and 5K travel on rolling ro..

Run the Fall Backyard Burn at Lake Fairfax in Reston on Oct 19, 2025. Choose a 5.1 mile lap or 10 mile option on mostly singletrack with roots, rocks and rolling climbs while supporting local nonprofit Homestretch.

Run For Your Life 5k is a cross-country 5K Run/Walk held at Verdun Adventure Bound in Rixeyville, Virginia (17044 Adventure Bound Trail). The race takes place on Verdun’s cross-country course across a 67-acre woodland setting, offering a tr..

The Crozet Trails Crew 5K/10K Trail Run + Family Fun Run is a fundraiser in Crozet, Virginia hosted by the Crozet Trails Crew. The course starts and ends at Crozet Park, following rustic trails east of the park with roots, rocks, and ruts...

Shenandoah Zombie Run is a 5K running event held at Camp Shenandoah in Swoope, Virginia. The course weaves through Camp Shenandoah’s hills and woods along Little North Mountain, offering forest trails as runners dodge zombies. Each particip..

Andy’s Backyard Ultra is a last-person-standing ultramarathon held at Teventrails in Earlysville, Virginia, about 14 miles northwest of Charlottesville. The event uses the Backyard Ultra format: competitors must complete a 4.17-mile lap wit..

Event The Halloween Horror event on October 26 takes place at Conway Robinson State Forest in Gainesville, VA. Distances offered: 5k 10k Walkers are welcome. A virtual race option is available. Points from the event count toward the 5k, 1..

Test your limits at the Great Eastern Endurance Run at Sherando Lake in the Blue Ridge Mountains on November 1, 2025. Choose 10, 20, or 40 miles of rugged single track, jeep roads, and scenic ridgelines for a true mountain trail experience.

Mountain Masochist Trail Run - Montebello, VA (Nov 1, 2025) The event offers these distances: 100K 50 Miler 50K The event takes place in Montebello, Virginia, with the course beginning and ending at the Montebello Campground. The listed a..

Ultra Race Of Champions is a mountain trail event held at Sherando Lake Recreation Area in the Blue Ridge Mountains of Virginia. Runners can choose from 40 miles, 20 miles, or 10 miles, with all races starting and finishing at the same venu..

Harvest Hustle 10k at Walnut Creek Park in North Garden, VA, offers a cross-country trail race with a 5k option as well. The course weaves through park woods with elevation changes, rocks and roots. The 10k features three water stations at..

Tackle rugged trails and scenic ridgelines at Fire on the Mountain, a challenging 50K with a 25K option in Little Orleans, Maryland. Cooler November air and lively aid stations make this a fall must for adventurous trail runners.