Trail Running calendar near Chesapeake City 2026-2027

Event Overview The Conestoga Trail Run is a 10-mile trail race in Holtwood, Pennsylvania. The event uses rocky and hilly trails with numerous small stream crossings. It is described as requiring experience and runners should be aware of pot..

This community 5K run/walk takes place on a wide natural trail at the Agricultural History Farm Park. The event includes a pre-race pep rally, post-race snacks, and awards for top finishers.

Run or walk through the rolling hills above French Creek at Camp Innabah. The five-mile trail race offers a mix of surfaces, while a two-mile fun walk is also available. All proceeds support summer camp programs and scholarships.

Run a 5K or walk the cross country trails at On Point Farm on Saturday, October 3. The event features live music, food, a bonfire and family activities, and proceeds support preservation of the Willistown countryside.

The Kettle Cooker Five & Dime is a trail race on the scenic and historic paths of Glenroy Preserve. Choose from four looped distances, all featuring hills, creek crossings, and ample aid station support. The event includes chip timing, a ra..

The Blues Cruise is a 50K trail ultramarathon looping around Blue Marsh Lake near Reading, PA. The scenic course features rolling hills, a single major climb, and themed aid stations. A relay option and a post-race party are also part of th..

Run through scenic vineyards and country roads at the White Horse Winery. Enjoy a flat course for a 10K, 5K, or 1-mile walk, followed by a party with live music and wine. All participants receive a tech shirt and souvenir glass.

Delaware Trail Fest celebrates the state's trails at Lums Pond State Park with a unique, fully age-graded race format. Choose from a 12-hour solo run, a 12-hour relay, a 24KM, or a 12KM lap course around the lake. All finishers get a sweats..

Event Overview The Mariners Bethel Trail Run is a multi-activity event at Camp Barnes in Frankford, Delaware. The main events are a 6.2 Mile Trail Run and a 3.1 Mile Trail Run. There are also three walking options of 1, 2, or 3 miles, and a..

The Patapsco Valley 50K offers a scenic trail run near Baltimore. Finishers earn unique awards, like a hand-thrown mug for the 50K. A virtual option lets you run your own course during the month following the event.

Get ready for an adventure on the trails at Parvin State Park. Choose between a classic half marathon or a choose-your-own-adventure 6-hour ultra on a mostly flat, fast loop. The event features a cupless, carry-in/carry-out format, emphasiz..

Explore the trails at Washington Crossing Park in New Jersey. The WXT Ultra offers 50K and 25K courses featuring scenic single-track and technical sections like Rock Hopper. Event proceeds support the local park association.

Experience a 50 mile trail run through the forested rolling terrain of the Seneca Greenway and Muddy Branch trails in Maryland featuring single track dirt paths and natural stream crossings.

Event Overview The Forbidden Run Fest is a trail running event held in autumn in Philadelphia's Wissahickon Valley Park. It is described as a celebration of the park during its peak autumn colors. The event is limited to 750 participants. D..

An 8K cross country run at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The mixed terrain course loops through grapevines and hop yards and finishers receive a complimentary tasting.

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

The Tuckahoe 25K returns for its 8th year on November 21, 2026. This 25-kilometer trail run features a mix of single track and horse trails with three fully stocked aid stations. The event proceeds rain or shine, offering awards and swag fo..

A community cross country event in Catonsville on Thanksgiving offering a chip timed 1 Mile Family Fun Run and a 5K. All proceeds support the CHS Cross Country program and awards include cash and age group prizes.

Enjoy a Thanksgiving 5K trail run through the scenic Autumn Lake Winery featuring dirt trails and grassy paths. This family friendly event supports animal rescue and welcomes strollers and leashed dogs on the course.

Experience a cross country Thanksgiving run at Vineland's Anthony Campanella Park. Open to all ages and paces, this event features awards for top finishers and supports the local public library.