Trail Running calendar near Parkton 2025-2026

Take on the Sweet Air Trail Race at Gunpowder State Park on July 12, 2026, a scenic out and back with rolling hills, faster stretches, water crossings and a bit of mud. Limited to 100 runners, entry is free and donations are welcome.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run through rolling vines at 868 Estate Vineyards in Hillsboro with a scenic but hilly 5k or 10k course that tests and rewards. Finishers get a medal, tech shirt and a glass of vineyard wine, and a virtual option is available.

Run the Vineyards at Bohemia Manor Farm offers scenic 5K and 8K courses through vineyards, waterfront and wooded trails, chip timed with live results. Finish with refreshments, a souvenir wine glass and an after party on the river.

Join Montey's Pack Rescue Run 5K at Heebner Park for a fun 5K, a 1 Mile Kids Fun Walk, or a virtual 5K that helps animals in need. Family friendly course with medals and fundraising prizes and 100% of proceeds support local rescue efforts.

Take on the MD Heat Trail Race in Patapsco Pickall near Elkridge with 25K and 50K options on rolling, technical single track with river crossings and rewarding climbs. Relax at the finish with food, beer and a festive post race vibe.

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.

Enjoy a scenic 5K trail or one mile Move As You Please at Thorncroft Equestrian Center’s 70 acre farm in Malvern. Finish with live music, food trucks and pony meet and greets while supporting care for Thorncroft horses.

Celebrate Labor Day with a scenic 5K through William Heritage Winery vineyards, plus family friendly 1 mile and kids races. Enjoy live music, food trucks and a souvenir wine glass while supporting the HEADstrong Foundation.

Join the Sasquatch Preservation Trail Run in scenic Seven Valleys, PA on September 12, 2026 for a fun 5K or 10K through rolling trails and forest scenery. Volunteers welcome to help keep this community event running strong.

Trails 4 Tails at Codorus State Park offers a scenic, rolling course for the 40 mile ultra, team relay or 25K with mixed singletrack, fields and lake views. Full aid station, camping and nearby lodging make it a fun day on the trails.

Join the Kettle Cooker Five & Dime at Glenroy Preserve for scenic loop trails with 5 mile, 10 mile and 25K options over hills, creeks and rocky terrain. Chip timing, aid stations, a soft tee and post race beer make it a great day.

Run scenic singletrack around Lums Pond State Park on October 17, 2026, at Delaware Trail Fest. Choose from solo or team 12 hour challenges or hiker friendly 24 km and 12 km lake loops for a day of fun and trail camaraderie.

Run scenic, historic trails in Patapsco Valley State Park with 50k and 25k options plus virtual entries that include same shirt and award. Enjoy well stocked aid stations, volunteer support, and a festive finish near CCBC Catonsville.

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run the scenic Turkey Trot at The Winery at Bull Run on Manassas National Battlefield with 5k and 10k options, in person or virtual. Enjoy a post race glass of wine, a finisher medal and tech shirt while supporting the Manassas Battlefield..

Run Thanksgiving at the 22nd Catonsville High School Turkey Trot featuring a chip timed 5K and 1 Mile Family Fun Run on a cross country course. Proceeds support CHS cross country and there are prizes; strollers and pets not allowed.

Celebrate the season at Milford Reindeer Stampede 5k at Killens Pond State Park on November 28 with a scenic run or competitive walk. Enjoy a long sleeve race shirt, post race treats and chip timing in this family friendly holiday event.

The Naked Nick is a low fee trail race at Blue Marsh Lake on December 13, 2026 with 25K and 50K on scenic single track and gravel that may be snowy or muddy. Finishers get mementos and chef prepared post race food.