Trail Running calendar near Chesapeake City 2026-2027

We have found 115 Trailruns within 80 miles of Chesapeake City. See below where and when you can find the races.

Test your endurance at the Genesee Valley Ultra on a 2.5 mile trail loop through Maryland farm roads and fields. Choose from 6, 12, or 24 hour individual or relay events with on site camping and chip timing.

Experience a unique trail run through the grounds of Genesis Church featuring a fun foam finish. Support healthcare services for the uninsured while enjoying distance options for runners, walkers, and children in York.

Experience a scenic trail run through the forests and fields of Rosaryville State Park. Choose from several distances on fast and smooth terrain located just off the Capital Beltway in Maryland.

Experience a trail romp through the scenic hills of Chester County at this annual charity event. Participants enjoy a five kilometer course followed by a pancake breakfast and an Easter Egg hunt for all ages.

Test your endurance in this last person standing event where runners must complete a 5K every hour to stay in the race. This self sufficient challenge continues until only one participant remains on the farm course.

Run along the paved B&A Trail in Maryland at this established event featuring a full and half marathon. Managed by the Annapolis Striders, it offers a well supported experience starting at Severna Park High School.

The Montchanin Trails 5K is a trail run on March 29, 2026, at Longwood at Granogue in Wilmington, DE. The 5K course features single-track trails, hills, and varied terrain. Registration is limited to 300 participants and includes a t-shirt..

Experience 7 miles of rolling hills and scenic single track trails at Cromwell Valley Park. Enjoy a fast downhill finish followed by pulled pork sandwiches and local beer at this community trail event.

April 2026

Experience a sanctioned 10K trail race through the historic Tyler Arboretum. Part of the USATF Mid Atlantic Off Road Grand Prix Series, this event offers a unique running opportunity on preserved natural trails.

Run the trails of Philadelphia's scenic Wissahickon Valley Park. Choose the marathon or half marathon on a course famed for its single-track paths and rolling hills. Finish with a medal, pizza party, and live music.

A turtle-themed 5K trail run at Hopkins Farm Brewery that supports local wildlife conservation. Participants receive a wooden medal and costume prizes are awarded. The event concludes with a festive after-party featuring live music.

Experience a unique trail run or walk through private farmlands and marsh ponds in Elverson. Enjoy post race festivities featuring search dog demonstrations and food prepared by an on site chef on this beautiful property.

The Fifth Street Rock Monster is a technical trail event on the private singletrack of Forever Farm. The 2026 edition features a new continuous loop course across five distances, camping, and a post race meal.

Join the Run to Remember in Sykesville for a variety of distances including 50K, 25K, and 5 mile options. Test your endurance in the 8 Hour Challenge organized by the Eldersburg Rogue Runners.

A 5K cross-country run at New Jersey's first farm brewery. The course winds through the scenic grounds of Screamin' Hill Brewery. All finishers get a coaster medal, and the after-party includes live music and a food truck.

Event Overview The 8th Annual Earth Day Trail Run is held at the Pennypack Ecological Restoration Trust in Huntingdon Valley, Pennsylvania. All proceeds from the event benefit the trust's efforts to protect open space and maintain its over..

Cross country running and walking event in Pottstown on 04/18/2026 offering 5 km, 10 km and a 1 mile walk. Registration is open with a posted entry fee and race day registration option.

The Gunpowder Keg Ultra features 25K and 50K trail races on a scenic 15.5-mile loop in Gunpowder State Park. Runners can even change their target distance mid race. The affordable entry supports the park and club, with optional commemorativ..

Experience a scenic 5K cross country race through the hop yards and vineyards of Red Shedman Brewery. Finishers enjoy a complimentary beverage at this unique farmhouse event in Mount Airy.

Course and Format The event is a 50-kilometer (31-mile) race along the Schuylkill River Trail. It starts and finishes at Saint Michael's Park, which adjoins Lock 60 in Mont Clare, Pennsylvania, adjacent to Phoenixville. The course follows t..