Trail Running calendar near Frederick 2026-2027

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 before Thanksgiving 3K and 6K at Barrel Oak Winery and Brewery in Delaplane, Virginia. In person and virtual options include medal and shirt choices; walkers and leashed pets are welcome.

A 48 hour out and back ultramarathon inside Sideling Hill Tunnel near Valley-Hi, PA. Runners cover just under 160 miles in repeated 1.3 mile laps while managing darkness and limited exits.

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 at Carderock Park on November 22, 2026, run on a flat, fast towpath. The event includes in-person and virtual options with medal and shirt choices.

A pre-Thanksgiving Turkey Trot at The Winery at Bull Run in Centreville, VA on November 25, 2026. On-site 5 km and 10 km routes run through the Manassas National Battlefield, with virtual entries and medal and shirt options.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

A trail ultramarathon in Prince William Forest Park near Triangle VA offering 50K, 100K and 100 mile loop courses. Well marked single track with staffed aid stations, limited entry and specific qualifying and time limit rules for each dista..

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.

A VHTRC holiday time 50k out and back on the Bull Run-Occoquan Trail from Hemlock Overlook to Fountainhead, with four aid stations and a GPX file for navigation. Entry includes lodge access, stocked aid stations, and a catered after party f..

Trail 5 km and 10 km races around Burke Lake Park in Fairfax Station on December 24, 2026. Virtual options are available and walkers are welcome.

A minimally marked 40.3 mile loop through the Massanutten Mountains that passes historic furnace ruins about halfway. The course has three aid stations, 6500 feet of climbing, and requires self navigation and self support.

A 31.7 mile New Year event in Prince William Forest Park run as three loops on groomed trails and some gravel roads. Unmanned aid at the start and finish is supplied by participants and entry is limited to 120.

A supported point to point mountain training run of 32 miles that follows much of the first third of the MMT 100, with two aid stations, required car shuttle, limited club support, and recommended GPX and turnsheet navigation.

A 50 km trail run at Hashawha Environmental Center in Westminster MD, featuring varied single-track, open fields, stream crossings and 5 aid stations. Entry for 2027 uses a lottery opening January 1, with indoor facilities and hot post-race..

The Elizabeth Furnace 50 km is a technical mountain trail race in the Massanutten range covering 30.5 miles and about 6,400 feet of ascent. Aid is limited with staffed stations near 10 and 22 miles so runners must carry personal supplies.

A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.

A 100 mile ultramarathon along the C&O Canal towpath near Knoxville, Maryland, featuring one ~40 mile loop and two ~30 mile loops beside the Potomac and multiple aid stations with volunteer support.

A last person standing endurance race in York, PA where runners repeat hourly loops until one remains. Entries include a designated parking and crew area, an event shirt, and a certified distance card.