Trail Running calendar near Highfield-Cascade 2026-2027

A 5k run and walk on May 25, 2026 at the historic Stoke estate in Middleburg, featuring open fields, rolling hills and forest along Little River. The course includes rugged, uneven terrain; children 12 and younger must be with an adult.

Four weekly 10K trail runs in May 2026 at the Pickall Area of Patapsco Valley State Park, organized by park stewards and timed by running time. Local sponsors support the series and Friends of PVSP members receive a $27 series discount.

A backyard ultra in Knoxville, Maryland where runners complete a 4.167 mile yard each hour until only one finishes. The event includes a 1-mile option, offers prize money for top finishers, and serves as a Backyard Ultra qualifier.

A 5k and 1 mile trail event at Gentle Giants Draft Horse Rescue in Mt. Airy, MD on May 30, 2026. The route crosses a 340 acre farm with draft horses nearby and features food trucks and mounted archery demonstrations.

ROCK CREEK 100 is a 100 mile looped trail event near Washington D.C. held May 30–31, 2026, consisting of ten 10 mile loops with about 8,200 ft of climbing and a 36 hour cutoff.

A scenic loop at Sky Meadows State Park on May 31, 2026, offering 5K and 10K courses with views of fields, streams and Turners Pond. Walkers are welcome and virtual entries are available with medal and shirt options.

A measured 100 mile loop through the Massanutten Mountains near Fort Valley, Virginia, featuring 14 significant climbs and mixed terrain. Runners have 24 hours to earn the silver buckle and 28 hours to finish.

A longstanding five-mile memorial run on the C&O Canal Towpath in Williamsport, MD, held June 6, 2026, with regular and student entries, chip timing, technical T-shirts, and awards for podium finishers.

A community trail event at Opossum Lake Park offering a 6 mile obstacle course, a 4 mile run, and a 4 mile walk on mixed terrain, with chip timing, age-group awards, and proceeds benefiting the Friends of Opossum Lake Conservancy.

Experience a timed ultra marathon on technical single track trails in the Blue Mountains. Run as many 3.5 mile loops as possible through the shaded landscapes of the Bashore Scout Reservation.

Trail races in Colonel Denning State Park offering 15K and 25K routes with significant elevation gain, multiple aid stations, and a strict 120 runner limit. Spectator access is limited and overall winners receive awards.

A community fundraising day at Burke Lake Park with a chip-timed 5k run and a noncompetitive 2k walk. The event supports programs for people with intellectual and developmental disabilities and includes awards, shirts, and post-event festiv..

Trail Trotters 5k & Fun Run is a community trail event at Promise Landing Farm in Upper Marlboro on June 7, 2026. The event features a 5k and a fun run; adult registration includes a T shirt and concessions with live music.

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.

Trail races on June 19, 2026 in Germantown, MD offering 6K and 12K courses around Button Farm and the Schaeffer Farm Trails. Walkers and several virtual entry options are available.

A night trail relay in Paradise, PA where teams and solo runners try to complete as many loops as possible in about 3 hours and 24 minutes on a marked 2 mile course. Team batons, glow rings, headlamps and on site divisions are used.

A blue-blazed out-and-back trail event near Frederick, MD offering 50K and 25K options on rocky, shaded trails with stream crossings, mandatory hydration, limited entries and staffed aid stations.

PUSO 5k & 10k on June 20, 2026 follows the Chesapeake & Ohio Canal path in Georgetown, Washington, DC. Runners and walkers can choose either a 5 km or 10 km distance, with registration fees varying by period.

Experience a scenic 5 mile trail run through Lancaster County Central Park featuring grass paths and water crossings. Compete for age group awards and enjoy a post race prize raffle in a beautiful natural setting.

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.