Trail Running calendar near Middletown 2026-2027

A measured 100 mile loop in Fort Valley, Virginia, through the Massanutten Mountains and Shenandoah River Valley with 14 climbs and about 14,000 feet of elevation gain. There is a 24 hour cutoff for the silver buckle and 28 hours to finish.

A five-mile towpath race in Williamsport, MD, held as the 45th annual Gary Brown Memorial event. Entries include standard and student fees, a guaranteed T-shirt deadline, chip timing with instant results, podium awards, and designated parki..

Teams and community meet at Burke Lake Park on June 6 2026 for a chip timed 5k run and a noncompetitive 2k fun walk, with awards, post-race food, and music.

Fox Trot 5k and 1 Mile at Merrie Mill Farm and Vineyard in Keswick on June 7, 2026 features a cross-country course, post-race cabana for participants, and a raffle with a gift basket valued at least $200.

A single-track trail race behind Zehmer Hall in Charlottesville covering about 3.1 miles, with steep climbs, technical footing, timing and bibs, and prizes for top finishers.

A night trail event in Prince William Forest Park offering a 50+ mile race made of two laps of a 25+ mile loop, plus 25M and 10M options. Aid stations are placed on course and crews are restricted to the Telegraph Road Pavilion.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K distances plus virtual options, with a hilly course around Button Farm and the Schaeffer Farm Trails and welcome to walkers.

Experience a 40 mile ultramarathon through the Monongahela National Forest and Dolly Sods Wilderness. This trail run features the natural beauty of West Virginia with a route based around the Canaan Valley Resort State Park.

A rugged out-and-back trail race near Frederick, MD, offering a 50K and a 25K Half Cat on rocky, shaded singletrack with stream crossings, three aid stations, and mandatory on-course hydration.

A 5 km and 10 km event along the Chesapeake and Ohio Canal path in Georgetown, Washington, DC on June 20, 2026. Walkers are welcome and registration fees vary by date with separate pricing for each distance.

A trail race in Canaan Valley State Park on June 27, 2026 with one loop of 5.9 miles or two loops for 11.8 miles on the Promised Land Trail, about 350 feet elevation gain per loop. Field is limited to 200 runners.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.

A 12 hour trail event on a scenic five mile single track loop in Berkeley Springs WV, featuring technical terrain with about 750 feet elevation per loop, on-course aid stations, a post race meal and handcrafted awards.

A mud-run fundraiser in King George, VA on June 27, 2026, featuring a 4-mile obstacle course and a 1-mile kids run, organized by the Dahlgren Lions Club with team awards by group size.

MCRRC Cross Country on the Farm Trail 5K is a trail race at Agricultural History Farm Park in Derwood MD. Non member registration is available for a $20 fee and the event is part of the club's low key race series.

A free 5K fun run on July 4, 2026 organized by Great Falls TrailBlazers. The loop course goes through the woods, meets at the Great Falls Library, is open to all ages and is pet friendly.

A trail-based running event at Needwood Lake Circle in Maryland on July 11, 2026 offering 5 km, 10 km and virtual entries with medal and shirt options.

A 5K and 10K event at Nottoway Park in Vienna, VA on July 11, 2026, with multiple virtual options and tiered entry fees.

A roughly 50 km trail ultramarathon on the southern Massanutten range with about 5,700 feet of elevation gain, six aid stations, and a post run gathering at the Route 211 commuter parking lot. Entry is limited to 75 runners.