Trail Running calendar near Chesapeake City 2025-2026

Join the 21st Annual Catonsville High School Turkey Trot on Thanksgiving morning for a family friendly 1 Mile fun run and a competitive chip timed 5K in Catonsville, Maryland. All proceeds support the CHS cross country program.

Kick off Thanksgiving in Vineland with the South Vineland Thanksgiving Run, a fun 3 mile cross country style course at Anthony Campanella Park. Family friendly, competitive awards, proceeds support the Friends of Vineland Public Library.

Join the Schuylkill Navy Run on Thanksgiving in Philadelphia for a spirited 5 5/8 mile challenge along Kelly Drive and Boathouse Row. Expect scenic river views, rolling hills and post race awards at Fairmount Rowing Association.

Enjoy the Williamstown Badgers Turkey Trot 5K at Autumn Lake Winery on Thanksgiving morning, a family friendly trail run over dirt, grass and sand. Run for a cause with proceeds to Honor Flight NJ and timed results with awards.

Join the Fifth Street Cross on Black Friday in Emmaus for a choose your distance running and riding event from 10k to 100 mile. Start anytime, lap the festive course and add to the prize pot by bringing a six pack or $20.

Join the festive 27th Milford Reindeer Stampede at Killens Pond State Park on November 29, 2025 for a chip timed 5K run or competitive walkers only 5K. Enjoy a long sleeve tee and a cozy post race party with treats and photos.

Join Phoenixville's 16th annual Burn Off the Bird 5K on November 29, 2025, along the scenic Schuylkill River Trail. Run in person or virtually, grab a swag shirt and custom medal, and support local causes while enjoying a chip timed course.

Shake off the winter chill at the Chilly Trail Run 5K in Haverford on December 6. Enjoy scenic trails, a cozy long sleeve race shirt for pre registered runners and light post race refreshments.

Join Team Foster's Last Person Standing on December 6, 2025 in Conshohocken along the Schuylkill River Trail for a backyard ultra where runners tackle repeated 4.2 mile laps until only one remains. Expect camaraderie, grit, and a central ai..

The Redman 9 mile trail race circles Redman Lake in York County on Saturday December 6, 2025, featuring scenic single track, about 1,200 feet of climbing and adventurous water tunnels. Enjoy a mid race aid station, post race snacks and fini..

Run the scenic 8.4 mile Loop Race in Philadelphia on December 7, 2025, tracing the Schuylkill River past the Art Museum and Boathouse Row. Not local? Join Loop Race Anywhere and run the distance anytime Nov 5 to Dec 7.

Tame the Tower Trail Challenge on December 13 in Lebanon, PA invites runners to tackle scenic 5 mile or 10 mile trail courses and enjoy a festive community atmosphere. All proceeds support Clarence Schock Memorial Park with trail maintenanc..

Run a festive 3 mile loop along the Manayunk canal on Dec 13 and bring canned goods to support North Light Community Center. Try Brooks shoes, sip hot chocolate and show up in your most festive holiday gear.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

Challenge yourself at Frosty Looper, an 8 hour timed race around scenic Cooper River Park on December 14, 2025. Mostly flat paved loops with a few hills, aid at the start and finish, and every finisher receives a custom race item.

Naked Nick is a scenic trail race at Blue Marsh Lake near Leesport PA offering 25K and 50K distances on mostly single track with challenging climbs. Expect rustic trail conditions and gourmet post race fare from a chef and pastry chef.

Run or hike the Sierra Club Lancaster Polar Bear 5K on January 10 in Lancaster County Central Park, a chip timed winter trail with hills and possible mud or snow. Dogs on leash are welcome and finishers and top placers earn awards.

Angela Ivory Memorial Trail Races at Killens Pond State Park on Jan 24 and 25 offer ultra distances including 50k, 100 mile and 24 hour events. The 50k is full with no wait list; enter another distance and drop in on race day if spots open.

Run the Mid Maryland Trail Festival at Rockburn Branch Park in Elkridge, MD, a scenic 50K on wooded trails made up of six loops of about 5.18 miles each. Solo runners or teams up to six can tackle the full distance or share loops in a relay..

Enjoy a scenic trail run along the Little and Middle Patuxent rivers in Columbia, Maryland. Choose from a half marathon, 10K or 5K on Jan 31 to Feb 1, 2026 at the Guilford Pratt Truss Bridge for a tame and rewarding trail experience.