Trail Running calendar near Chesapeake City 2026-2027

Nighttime 10 km trail run in Reading, PA where runners provide their own lighting and follow glow markers on rustic trails, finishing at the Liederkranz German club.

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 in Rosaryville State Park offering 50K and 20K single-track loops, organized by the Annapolis Striders. The event is limited to 250 runners and includes aid stations, a drop-bag area, and time limits for each distance.

A multi-race event on November 15, 2026 featuring half marathon and marathon options along the D&L Trail, finishing in downtown Easton. The festival includes a USATF-certified marathon, relay divisions, and proceeds that support the D&L Cor..

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 free 5K cross country at Herring Run Park with an XC style start, mixed surfaces and technical single track, donations accepted for local scholarships and park support.

A 25K trail race in Queen Anne, MD on November 21, 2026 with mostly single-track trails, three stocked aid stations, awards for top three men and women, and organization by Algonquin Ultras and the Centreville Crushers.

Start your Thanksgiving with a low key run at the Moorestown High School cross country course. Choose between a 5K and a one mile fun run with snacks and drinks available for all participants.

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..

A 5K and 10K held in Wheaton Regional Park on November 26, 2026, featuring mixed gravel, trail, and paved paths plus virtual options with medal and shirt choices.

A 5K at Eastern Regional Park on Thanksgiving Day, 11/26/2026, run over two laps of the park outer loop with paved and natural surfaces plus wooden bridges. Open to all ages; registration runs Aug 1 to Nov 1 for a $15 fee.

The Fifth Street Cross 100 will take place in Emmaus on Friday 27 November 2026. You can run between 10 and 100 kilometers.

A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, and post race refreshments.

A holiday running event in Washington, DC with 5K, half marathon, marathon and virtual options on the C&O Canal path, held December 6, 2026.

An eight hour endurance run at Terrapin Nature Park where participants complete 2.8 mile laps to earn surprises placed in a personal stocking. Awards are given to the male and female with the most laps.