Trail Running calendar near Chesapeake City 2026-2027

A trail and road mix half marathon and an all trail 5K centered at Sleepy Hollow Athletic Club. Both races run largely on the Horse Shoe Trail and support Berks County Special Olympics.

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 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.

Say My Name 5k and 1 mile Walk in Lewes raises funds for Rylie’s Smile Foundation while participants run or walk the Cape Henlopen State Park Trail. The event includes a virtual 5K option, commemorative signage, post-event awards, and race..

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.

Half and full marathons on a shaded paved bike trail along Pennypack Creek in Philadelphia. Aid stations, disposable chip timing, finisher medals and a Bavarian themed post race party with snacks and nonalcoholic beer included.

Goliathon is a nonprofit ninja warrior style obstacle course run in Mullica Hill, NJ, with a roughly four mile course and 12 tiered obstacles (G1 G2 G3). Teams and individuals may compete; proceeds support clean water projects.

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.

A free, timed 5K trail run at Crystal Lake Park on June 6, 2026, with a technical course of about 300 feet of elevation gain and a 40-runner field limit. Awards and a midway water station are provided.

A trail event in Wissahickon Valley Park on June 6, 2026 offering a 10K race and a 1 mile family nature walk. Proceeds support Friends of the Wissahickon for trail and watershed stewardship.

The Run for Woods 5K will take place in Langhorne Manor on Sunday 7 June 2026.

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.

The Jerseys4Kids Run Against Pediatric Cancer will take place in Bala Cynwyd on Sunday 7 June 2026.

A community trail event at Paradise Farm Camps on June 11, 2026, offering a 5-mile run, a 5K, and a 1.5-mile family walk/run. All proceeds fund East Bradford Township's public trail program and trail development.

A last person standing backyard ultra at South Mountain Preserve with a 3.4 mile loop and 350+ ft of climb over rugged terrain. The event also features an evening Blackout one loop race and a beer mile.

A 5K road race in Dewey Beach on June 14, 2026 that benefits the Dewey Beach Patrol and is part of the Ten Sisters series. The event includes a competitive walking category, chip timing, tech shirts, and a post race party with food and beer..

A night trail relay in Paradise, PA where teams pass a baton and collect glow rings to count loops. Runners aim to complete as many 1 mile loops as possible in a 3 hour 24 minute timed period; headlamps recommended.

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.

An all-day looped trail event at Tyler State Park on June 20, 2026, with alternating-direction 5 mile trail and paved loops over an 11 hour window. Entry is $25 and Bucks County Road Runners members may be eligible for free or reduced entry..

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.