Trail Running calendar near Frederick 2025-2026

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

Devil Dog Ultras is a challenging trail running event held in Prince William Forest Park near Triangle, Virginia. It offers three race distances: 100 miles, 100K, and 50K. The course features primarily single-track trails with some roots, rocks, and brief technical sections, along with fire roads an..

The Fall Backyard Burn Trail Run at Fountainhead Regional Park in Fairfax Station, VA, is a popular trail running event held on December 7, 2025. The race offers two challenging distances: a 4.8-mile loop with 450 feet of elevation gain and a tougher 10.5-mile course featuring an additional out-and-..

The Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon held at Rockburn Branch Park in Elkridge, Maryland. The course consists of six loops, each approximately 5.179 miles, winding through wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members, exchanging..

No Man's 50K is a women-only trail running endurance event held in Triangle, Virginia, featuring distances of 25K and 50K. The course consists of two loops of approximately 15 miles each, designed as a great first-time ultramarathon route. Runners experience a mix of terrain with about 70% single tr..

The Capital Backyard Ultra is a challenging endurance running event held at Meadowood Special Recreation Management Area in Lorton, Virginia, near Washington DC. This Silver Ticket race features a unique format where participants run a 4.167-mile loop every hour, starting on the hour, continuing unt..

The Genesee Valley Ultra is an endurance running event held at the Genesee Valley Outdoor Learning Center in Parkton, Maryland. It features a 2.5-mile trail loop through farm roads, grass fields, and some double track on private property. Participants can choose from 6, 12, or 24-hour race durations..

The Bull Run Run (BRR) 50 Miler is a classic 50-mile trail race held annually in Clifton, Virginia, within Hemlock Overlook Regional Park. Established in 1993 and organized by the Virginia Happy Trails Running Club, it is one of the oldest 50-mile races in the U.S. The course features forested, roll..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun run, offering participants a scenic course winding through a..

Run to Remember in Sykesville, MD, is a memorial running event held at Piney Run Park featuring distances of 50K, 25K, 5 miles, and an 8-hour challenge. The course is a scenic 5.25-mile loop through woods and meadows, with about half the route offering lake views. Runners complete multiple loops dep..

The C&O Canal 100 is a 100-mile ultramarathon held in Knoxville, Maryland, along the scenic C&O Canal towpath near the Potomac River and Appalachian Mountains. The course features one approximately 40-mile loop followed by two 30-mile loops, starting and finishing at Camp Manidokan. Runners enjoy te..

The Farm Park Challenge is a unique trail running event hosted by My Muddy Shoes at the Agricultural History Farm Park in Montgomery County, Maryland. Participants can choose from three timed challenges—3-hour, 6-hour, or 10-hour—where runners must complete one lap of the course each hour, resting o..

The Massanutten Mountain Trails (MMT) 100 Mile Run is a challenging ultramarathon held in the Massanutten Mountains within Virginia’s Shenandoah Valley. Starting and finishing at Caroline Furnace Lutheran Camp in Fort Valley, VA, the rugged course features rocky trails and steep climbs totaling over..

The More Miles Last One Standing Challenge is an endurance running event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile loop, known as "the yard," every hour on the hour, completing each lap within the hour to continue. The race continues un..

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This unique event tests runners' versatility across multiple ter..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, a historic site once used to train World War II OSS spies, predecessors to the CIA. The race features a 50-mile distance composed of two laps on a 25+ mile loop primarily on single-track trails..