Trail Running calendar near Chesapeake City 2025-2026

The Bull Run Reunion Run 2025 is a 3-mile cross country race held in Parkton, Maryland, at Hereford High School. Scheduled for September 20, 2025, this event is part of the Bull Run Cross Country Invitational and is open to all ages. The Reunion Run is the seventh race of the day, offering participa..

St. Anselm's Family 5k is a family-friendly fundraising race in Washington, DC, held at 4501 South Dakota Ave NE. The event covers a 5k distance on a double-loop trail course, suitable for runners and walkers alike.It benefits a memorial scholarship fund at St. Anselm's Abbey School, supporting stud..

The 9th Annual Cancer Warriors 5k takes place on September 20, 2025, on the Ma & Pa Trail in Belair / Baltimore, MD. The event is organized by Cancer Warriors Inc., a certified 501(c)(3) nonprofit. All proceeds go to cancer research institutions. An afterparty is scheduled at Independent Brewer..

The Kellie Thompson Shiley 5k and Family Fun Run is an annual event held at the Terrapin Nature Trail in Stevensville, Maryland, on the scenic Eastern Shore. It features a 5K trail run/walk and a 1-mile fun run for children aged 10 and under. The race honors Kellie Thompson Shiley’s competitive spir..

Cedar Run's Trails, Tails & Ales is an annual 5K charity trail run held at Woodford Cedar Run Wildlife Refuge in Medford, New Jersey. The event features a scenic, exclusive trail course starting and ending at the Nature Center Pavilion. Participants receive a limited edition event t-shirt, light bit..

Ultra Trail DE is a 6-hour trail running event held on private Longwood Gardens property at 2900 Montchanin Road in Wilmington, Delaware. Runners tackle roughly a 5-mile marked loop with about 700 feet of elevation gain per lap, featuring creek crossings, twisty singletrack, grass and gravel, and oc..

On Saturday, September 27, 2025, Red Devil 5K is a community cross-country race in West Grove, Pennsylvania, hosted at Avon Grove Middle School by Avon Grove High School. The rolling, three-loop course is mostly grass with some pavement and finishes on the track; it is the same course used by the AG..

THE Conestoga Trail Run - 10 Tough Miles is a rugged trail race held in Holtwood, Pennsylvania, along Kelly's Run and the Conestoga Trail. The 10-mile course combines rocky, hilly terrain with several stream crossings, offering scenic hilltop views of the Susquehanna River and Mountain Laurel. Runne..

Bear Trail Half Marathon & 10K takes place at Lums Pond State Park in Bear, Delaware, starting and finishing at Area 1. The course uses sections of the Little Jersey and Swamp Forest trails, combining single-track and wide trails with relatively flat elevation, making it approachable for runners of..

Cornwall Elementary 5K & 1-Mile Fun Run is a family-friendly event held at Cornwall Elementary School in Lebanon, Pennsylvania. The race offers two distances—a 5K and a 1-mile fun run—on the Lebanon County Rail Trail. Now in its 11th year, it invites runners and walkers of all levels to participate..

Blackout in Emmaus, PA is a rugged nighttime 10K trail race, with 1,000 feet of elevation gain over technical, mountainous terrain. The Running Kind presents a 'Lights On' edition allowing an early dusk start for those who want to begin before darkness settles, and the traditional option. The race s..

Run-a-Muck, hosted by the Willistown Conservation Trust, takes place in the Willistown countryside (Newtown Square, PA). Participants can choose a 5K run or muck (walk) on a cross-country trail described as diverse terrain. The event blends sport with a festive atmosphere, offering food, beer, wine,..

Trails4Tails is a dog-friendly trail running event held at Historic Washington Crossing Park in Titusville, NJ, with the start area at the Phillips Farm Recreation area off Bear Tavern Road. It offers three distances: a 1 Mile Fun Run (with or without a dog), a 5K, and a 5K with Dog. The course is a..

The 5th Annual Octoberfest 5K is a community running event in Haddonfield, New Jersey, starting and finishing at Maria Greenwald Softball Field. The race offers a 5K run with an updated course map and on-site parking, plus nearby downtown parking. After crossing the finish line, participants gather..

Camp Innabah Fall Classic, held at 712 Pughtown Road, Spring City, PA 19475, features a 5-mile trail race and a 2-mile fun walk. The five-mile course traverses dirt trails, gravel roads, and short paved sections over rolling terrain above French Creek in Chester County, offering a hilly, scenic chal..

The Blues Cruise is a 50K trail ultramarathon held near Reading, Pennsylvania, celebrating its 20th anniversary in 2025. The scenic 31-mile loop circles Blue Marsh Lake, featuring varied terrain including fields, rolling hills, single track, and less than half a mile of public road. The course inclu..

The Kettle Cooker Five & Dime Trail Race, held at Glenroy Preserve in Nottingham, Pennsylvania, offers three trail distances: 5 miles, 10 miles, and 25K. Runners navigate hills, creek crossings, and mixed terrain on well-maintained singletrack and fields, with some sections threading through histori..

Located at 889 Croton Road, Wayne, PA 19087, the McKaig 5K Trail Race celebrates its 10th anniversary this autumn. The event offers a 5K trail race, Monkey Rock Miler, Kids Race (Free), and Chili Cook-Off. The festival atmosphere includes vendors, music, post-race food and beverages, and free chili..

The WCU Cross Country Golden Ram Invitational takes place in Kennett Square, Pennsylvania, on the campus grounds of Patton Middle School and Unionville High School at 760 Unionville Road. The meet includes men’s and women’s 5K races. The course is grass-dominated, laid out as two 2K loops plus a 1K..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. The course is a natural trail through the park, with water st..