Trail Running calendar near Sykesville 2026-2027

Shake off winter at Creek's Edge Winery with the Run First Wine Later 3k and 5k on March 7, 2026. Scenic loops, chip timing, a finisher medal, tech shirt and a postrace glass of wine make this a fun social outing for runners and walkers.

Run the Smoketown Brewery 5k or 10k in Brunswick MD on March 8, 2026, a flat out and back on light gravel. Virtual entries and walkers welcome, with chip timing, a finisher medal, tech shirt and beer while supporting Wear Blue Run to Rememb..

Blazing Saddles at Codorus State Park offers 8 Miler, 25K and 50K trail challenges across singletrack with runnable hills, mud and possible snow. Early registrants get swag and proceeds benefit a local animal rescue.

Run through vineyards at Armstrong Valley Winery in a chip timed 5k over varied footing for a fun wine country challenge. Entry includes a T shirt, wine glass, medal that doubles as a wine stopper and a wine pour. Virtual entries welcome.

Join the Spring Backyard Burn Trail Run at Laurel Hill Park on March 15, 2026 with 5 and 10 mile courses across forested fire roads, singletrack and stream crossings. Start and finish beneath the historic Workhouse guard towers for a scenic..

Tackle the HAT Run 50K ultramarathon in scenic Havre de Grace, Maryland on March 21, 2026. Expect winding single track, nearly 4,400 feet of climbing and several stream crossings that may get your feet wet.

Run a scenic 4k or 8k on the rolling grounds of Twisted Oak Farm Brewery in White Post, VA. Enjoy chip timing, a finisher medal, a tech shirt and a complimentary glass of beer, with a virtual option available.

Run among saplings and open fields in the Breeze Thru The Trees 5K or enjoy a relaxed 1 mile fun run on Ruppert Nurseries' scenic tree farm in Gaithersburg. Proceeds benefit the Montgomery County Children's Opportunity Alliance to expand ea..

Join Washed Clean in York PA for a fun trail 5K, 1 Mile Walk, and free Kids Fun Run with a foam finish and bumpy scenic course around Genesis Church. Family friendly with strollers welcome and proceeds benefiting local nonprofits.

Run through the woods and open fields of Rosaryville State Park with half marathon, 10K and 5K trail options plus virtual entries for March 28, 2026. Enjoy twisty but smooth, mostly flat trails hosted by EX2 Adventures.

Hit the scenic B&A Trail in Severna Park on March 29, 2026 with marathon and half marathon options, the marathon a Boston qualifier. Enjoy a mostly flat rails to trails route, generous aid, a finisher medal and participant apparel.

Run the Bull Run Run 50 Miler on April 4, 2026 in Clifton Virginia, a 50 mile trail through rolling forest and spring bluebells along the Bull Run Occoquan Trail. Civil War themed course, riverside views and a 13 hour cutoff.

Enjoy a scenic three loop 5k through Molon Lave Winery in Warrenton on April 4, 2026. Walkers and virtual runners welcome and finishers receive a winery glass, medal and tech shirt for a festive post race celebration.

Relaxed 14 mile point to point run along the scenic Dahlgren Railroad Heritage Trail in Virginia with gentle elevation. Quirky aid stations serve pie, s'mores and pretzels and finishers receive practical swag while supporting local charitie..

Join the Trail Demon 5k and 10k at Dirt Farm Brewing in Bluemont, VA on April 4, 2026, with in person or virtual entries. Expect technical forest trails, a finisher medal, tech shirt, chip timing and a post race beer.

Join the Turtle Derby, a turtle themed 5K on brewery trails supporting Susquehannock Wildlife. Enjoy a wooden finisher medal, costume contests, awards, live music and on site beer.

Run rugged trails with creek crossings and climbs at Buck Ridge Burn in Pine Grove Furnace State Park on April 12, 2026. Choose a half marathon, 10K, 5K or virtual option and enjoy small fields, handmade medals and a finisher coaster.

Run to Remember on April 18, 2026 at Piney Run Park in Sykesville offers looped trail races from 50K to a 5 miler and an 8 hour challenge. Honor club members while supporting youth programs, a scholarship and cancer research.

Experience a scenic 5k atop a ridge in apple country with cross country terrain, orchard views and a post race wine pour. Family friendly with virtual options, the event supports Nik's Wish and offers fun keepsakes for finishers.

Run 3k or 6k through Barrel Oak Winery vineyards in Delaplane VA on April 19, 2026 for a rolling cross country experience. Enjoy a glass of wine, a medal and tech shirt while supporting Semper Fi and America's Fund; virtual and pet friendly..