Trail Running calendar near Rosaryville 2026-2027

Run scenic, moderately technical trails at Schaeffer Farms in Germantown, starting and finishing at the Button Farm Living History Center. Choose a 5K or 10K for a rooty, stream crossing adventure while supporting local charities.

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.

Tackle twisty single track and rolling hills at Little Bennett Regional Park in the Blue Crab Bolt Trail Run, offering 5K and 10K options on scenic, streamside trails. Optional donations benefit Interfaith Works for local families.

Pick a 5k, 10k, or half marathon on scenic gravel trail loops with chip timing, a finisher medal and a technical shirt. Run in person or virtually, earn series points and support Operation Enduring Warrior.

Run rugged single track and river crossings at MD Heat Trail Race in Patapsco Pickall, Elkridge MD. Choose 25K or 50K and expect big climbs, technical rock sections, helpful aid stations and a finish with food and beer.

Enjoy a scenic trail 5k or 10k through Leopold's Preserve in Broad Run, Virginia on Aug 23, 2026, with chip timing, medals and a tech shirt. Walkers and virtual participants are welcome and races earn points toward year long series.

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.

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.

Run through Creekside Farm on scenic dirt trails along the Rappahannock River with 5K and 8K options, chip timing and awards. Celebrate after with live music, craft beer, a free pint for entrants 21 plus and food trucks.

Push your limits at the Pemberton 24, a 24 hour running challenge at Pemberton Park in Salisbury MD on September 18 to 19, 2026. Run hourly 5K loops solo or with a four person team, rest at your camp, and chase points and nightly bonuses.

Choose from a 25K, 40 Mile or 40 Mile relay on scenic mixed terrain at Codorus State Park, featuring lakeshore singletrack, open fields and historic sites. Enjoy a fully stocked aid station, race day picnic and finisher awards.

Run with your dog at the Howlin' Coyote Canicross Trail Race in Caledon State Park, featuring varied terrain and a 10 km canicross plus a one mile Wild Pup dash. This non profit event supports Friends of Caledon and is disposable cup free.

Scenic trail running at Milkhouse Brewery in Mount Airy with a 5 Mile race and 4 Hour and 8 Hour ultra challenges. Presented by the Frederick Steeplechasers to honor Rick O'Donnell and raise funds for local scholarships.

Experience scenic, historic trails of Patapsco Valley State Park with the 50K and 25K on Oct 24, 2026, offering in person and virtual options. Finishers earn special swag including a hand thrown mug for 50K completers.

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..

Run Schaeffer Farms singletrack in Germantown on Saturday, November 7, 2026 with half marathon, 10K and 5K options. In person and virtual entries welcome; proceeds support Interfaith Works for a fun, challenging trail day.

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.

Enjoy a crisp fall trail run at Hemlock Overlook, winding through forests, fields, stream crossings, and scenic Bull Run views. Choose a 5 or 10 mile course with plenty of spots for friends and family to cheer.

Run a rugged 25k through scenic single track and horse trails in Queen Anne, Maryland on November 21, 2026. Expect runnable hills, muddy rooty sections, three stocked aid stations, and a lively race vibe with swag and awards.

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..