Trail Running calendar near Bear 2026-2027

Trail races at Kelly's Run Nature Preserve in Holtwood on May 16, 2026 include chip timed 10K and 5K courses plus a free kids trail race of about 1.5 miles. The 10K features 1,256 feet of elevation and an aid station at Pinnacle Overlook.

Test your resilience in this 24 hour endurance challenge in Annapolis. Set your own mileage goals to honor military heroes while enjoying provided meals and a community trail running environment.

A morning 5K held during the Fair Hill Scottish Games on May 16, 2026, with a $40 entry that includes game admission; on-site cash entries and ATMs are available, and cash prizes plus a trophy and Scottish claymore are awarded to top finish..

Experience the scenic beauty of the Brandywine Valley through forests and farmland. Choose between 10k, 25k, and 50k distances in this part of the USATF Mid Atlantic Off Road Series.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

Tough Mudder Philly on May 23, 2026 at Plantation Field offers 5K, 15K and Infinity obstacle runs with named obstacles, finisher items, spectator festival access, and group and volunteer options.

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.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

A community 5K and 1-mile walk in Lewes, DE on May 30, 2026 benefiting Rylie’s Smile Foundation, with in-person and virtual options, memorial signage along the Cape Henlopen State Park Trail, post-race pavilion activities, and chip timing.

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.

A non-profit, ninja-warrior style obstacle course run in Mullica Hill, NJ featuring a roughly 4-mile course with 12 tiered obstacles, team scoring by obstacle tiers, and proceeds supporting 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.

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 on a 3.4-mile, 350+ ft elevation trail loop at South Mountain Preserve, with a chip-timed nighttime Blackout loop, zero carbon measures, and community donation programs.

Join the 24th Dewey Beach Patrol 5k in Delaware for a series road race ending with a post-race party on the bay. This chip-timed event offers categories for both runners and competitive walkers.

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.

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.