Trail Running calendar near Hillsboro 2026-2027

Experience the 15th annual Sasquatch Preservation Trail Run in Seven Valleys. Choose between the 5K or 10K courses and explore the natural landscapes preserved by the Farm and Natural Lands Trust.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

Trails 4 Tails offers a 40-mile ultra, a 40-mile team relay, and a 25K on a scenic multi-loop course through Codorus State Park. The trail route features varied terrain and changes direction each year. All races finish at a stocked pavilion..

Conquer a challenging 10-mile loop at Seven Bends State Park in this multi-distance trail event. Choose from a 100-miler, 50-miler, 50k, 10-miler, or a Last Man Standing Ruck format. It's a cup-less race where strategy and resilience meet s..

Event Information The River's Edge Endurance Challenge takes place in Brunswick, Maryland. The event is the 8th annual edition and offers three different race distances. Distances 5K (3.1 miles) 3 Hour Endurance Race 6 Hour Endurance Chall..

Join the 7th annual Trails 4 Miles for a fall challenge at Sherando Park. Choose from a mixed-surface 4-mile trail run, a new mountain bike time trial, or a one-mile fun run/walk. All proceeds support the I'm Just Me Movement.

Join a community 5K run and walk through the scenic trails of Agricultural History Farm Park. Enjoy a morning of music and fitness with events for all ages and awards for top finishers.

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.

Experience the beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.

Experience a scenic trail run at Lake Fairfax Park in Reston featuring singletrack loops with lake views. Choose between 5 or 10 mile distances while supporting local families through a community charity partnership.

The Patapsco Valley 50K offers a scenic trail run near Baltimore. Finishers earn unique awards, like a hand-thrown mug for the 50K. A virtual option lets you run your own course during the month following the event.

Experience a seasonal trail run or walk through the scenic Conway Robinson State Forest in Gainesville with 5k and 10k distance options for all participants.

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

Trail runners head to Maryland's Green Ridge State Forest for the Fire on the Mountain 50K and 25K races. The event features technical trails, forest roads, and strict cutoff times. It's scheduled for November 1, 2026, with a training run o..

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

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.

An 8K cross country run at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The mixed terrain course loops through grapevines and hop yards and finishers receive a complimentary tasting.