Trail Running calendar near Woodstock 2026-2027

A weekend of obstacle races at Massanutten Resort on October 24-25, 2026 with Sprint 5 km, Super 10 km and kids races on mountain trails featuring rocky terrain and steep climbs. Team entries can secure the same start time and eligible staf..

Event Format Andy's Backyard Ultra is a "last person standing" ultramarathon. Runners must complete a lap of 4.17 miles every hour to remain in the race. The event continues until only one runner remains; that runner must then com..

Runnable, rolling trail loops in Prince William Forest Park offer **50 km** (two 16-mile loops) and **25 km** (one 16-mile loop) options on shaded trails with creek crossings. Entry is limited to 110 runners and there is no formal entry fee..

A fall trail fundraiser at Crozet Park offering a 5K, 10K and a 0.75-mile Family Fun Run, with T-shirts, overall awards, a creek crossing on the 10K, and a post-race trails fest with pancake breakfast and music.

Trail races at Conway Robinson State Forest Park in Gainesville, VA on October 25, 2026 offering 5 km and 10 km courses plus virtual options with medal and shirt choices.

Experience a scenic 5K cross country run through the historic Rocklands Farm Winery followed by an after party with live music and wine.

Fire on the Mountain in Little Orleans, Maryland, on November 1, 2026, offers a 50K and a 25K on forest trails and service roads in Green Ridge State Forest. Both courses include multiple aid stations and official cutoff times.

Trail races at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

A mountain trail ultramarathon in Montebello, Virginia offering 100K, 50 miles and 50K routes across single track, dirt and gravel through the Blue Ridge, with start and finish at Montebello Campground and key aid stations on course.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Trail races at Walnut Creek Park on November 8, 2026 offering 5K and 10K distances plus virtual entries with medal and shirt options. Registration fees vary by entry type and by registration date.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre-Thanksgiving event at Barrel Oak Winery and Brewery offering in-person 3K and 6K races plus several virtual options; walkers and leashed pets are welcome and registration fees vary by entry type.

A trail race at Riverbend Regional Park on November 22, 2026 offering 5 mile and 10 mile routes on riverside singletrack with aid stations, post-race food, parking, and a kids program.

A 5K and 10K held at Carderock Park along the Chesapeake and Ohio Canal Towpath on November 22, 2026, with a flat, fast trail, walkers welcome, and virtual entry options that include medals and shirts.

A pre-Thanksgiving Turkey Trot at The Winery at Bull Run on November 25, 2026 featuring 5 km and 10 km courses through Manassas National Battlefield trails. Virtual entry options are available with different medal and shirt choices.

A roughly 10 mile trail and canal run near Great Falls on November 26, 2026. Entry opens November 12 and is limited to 29 runners, and participants are responsible for their own medical care.

Lake Anna Turkey Trot at Lake Anna State Park on November 27, 2026 offers 5k, 10k and half marathon courses. The 5k is a trail run while the 10k and half are half trail and half paved; walkers are welcome.

A looped trail ultramarathon at Prince William Forest Park with 50K, 100K and 100 mile options, staffed and unmanned aid stations, set time limits, a 300 runner cap, and a multi year loyalty challenge.

Trail runs at Fountainhead Regional Park on hiking trails and old dirt roads with 4.8- and 10.5-mile options, aid stations, post-race food, and a kids race and program for ages 2-11.