Trail Running calendar near Woodstock 2026-2027

Mountain Masochist Trail Run in Montebello VA features 100K, 50 mile and 50K courses through rugged Blue Ridge single track and forest roads at peak fall foliage. Finish at Montebello Campground with aid stations and a post race meal.

Enjoy a crisp fall trail run at Hemlock Overlook, winding through forests, fields, stream crossings, and scenic Bull Run views. Choose a 5 or 10 mile course with plenty of spots for friends and family to cheer.

Run the scenic Turkey Trot at The Winery at Bull Run on Manassas National Battlefield with 5k and 10k options, in person or virtual. Enjoy a post race glass of wine, a finisher medal and tech shirt while supporting the Manassas Battlefield..

Run scenic trails along the Occoquan Reservoir at Fountainhead Regional Park for the Fall Backyard Burn Trail Run. Choose a spirited 5 Mile or a challenging 10 Mile course with rolling climbs and great views.