Trail Running calendar near Chesapeake City 2026-2027

Trail races of 50k and 25k take place in Patapsco Valley State Park on October 24, 2026 with in-person and virtual options. All entrants receive event apparel and a finishers award, and virtual runners have Oct 24 to Nov 24 to complete thei..

Trail races at Parvin State Park offer a half marathon and a 6 hour lap event on a mostly trail lollipop loop. The event is cupless and uses an aid station at the start and finish.

A trail ultramarathon at Washington Crossing Park on October 24, 2026, offering 25K+ and 50K courses across historic, technical singletrack with multiple aid stations and finisher swag.

A 25K trail race in Ridley Creek State Park, Glen Mills, PA, on October 25, 2026. The single loop features about 1,800 feet of climbing, technical trails, three aid stations and a five hour finish cutoff, with prizes for top three men and w..

A backyard ultra scheduled for October 31, 2026 at Shawan Downs with repeated 4.167 mile loops. Runners complete as many loops as they can over a 24 to 48 hour period.

A charity trail event at Gifford Pinchot State Park featuring a 5k run and a 3.5k walk with dog-focused awards, proceeds supporting canine cancer research, and a free children's dash for ages 10 and under.

An endurance running event in Woodbine NJ offering 6-, 12- and 24-hour individual races plus 12- and 24-hour relays. The course uses 5.5-mile dirt laps with few roots and the venue provides camping, cabins, showers and a sauna.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Experience an off-road race weekend at Yeager’s Farm & Market featuring 4 and 10 mile trail runs. Enjoy a local atmosphere with post-race beer and bagels and earn a unique long sleeve tech shirt.

A trail and gravel running event in Wissahickon Valley Park offering 10 km, 10 mile and half marathon options with chip timing, aid stations, limited field size, and a post-race party with live music and warm food.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

Trail races at Rosaryville State Park in Upper Marlboro offer 20K and 50K on a 9.5 mile single track with wooded scenery, aid stations, a nearby drop bag area, and participant limits and time cutoffs.

A one day trail festival at Independence Park on November 15, 2026, offering multiple distance races, 3 hour and 6 hour lap events, and a 2 mile walk. Live music, food trucks, and local vendors support East Vincent Parks.

A 5K cross country race at Herring Run Park on November 15, 2026, featuring mixed paved, field and technical single track surfaces. Entry is free and donations are accepted for scholarships and Friends of Herring Run Parks.

A 25K trail race in Queen Anne, Maryland on November 21, 2026, organized by Algonquin Ultras and the Centreville Crushers. The mostly single track course features runnable hills, rooty and muddy sections, three aid stations, and awards.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

A trail 5K at Autumn Lake Winery in Williamstown, NJ on Thanksgiving morning with dirt, grass, and sand underfoot. Awards for the top three male and female finishers, free entry for kids 14 and under, and a portion of proceeds support Lucky..

A cross country style 3 miles race at Anthony Campanella Park in Vineland, NJ, welcoming runners and walkers of varying ages. Awards for top overall finishers and multiple age groups; online registration with several payment options.

A historic Schuylkill Navy road and cross country race covering 5 and 5/8 miles of hilly and grassy terrain along Kelly Drive and Belmont Plateau. Club eligibility, multiple age divisions, team scoring, posted results and an on site awards..