Trail Running calendar near Winchester 2026-2027

Tackle a scenic 50K trail ultramarathon at Rockburn Branch Park on six wooded loops of about 5.2 miles each. Race solo or as a team of 2 to 6 with stocked aid stations and a friendly festival atmosphere.

Run the Patriotic Pursuit on Jan 31, 2026 at Williamsport Park: chip timed 5k, 10k and half marathon along a flat gravel C&O Canal trail. Medal, technical shirt and virtual option included; proceeds benefit Semper Fi & America's Fund.

Join the Little Patuxent River Half Marathon, 10K and 5K in Columbia MD on Jan 31 to Feb 1, 2026 along gentle trail sections by the Patuxent. This edition is sold out, but finishers get shirts, medals and knit gloves.

Brave wooded trails at Prince William Forest Park on Feb 1, 2026 with distances from 5k to 50k, featuring technical hills, roots and scenic views. Support Semper K9 and earn medals, tech shirts and chip timing in this winter trail challenge..

Join ICY 8 at Lake Anna State Park for scenic figure 8 trail running with options from an 8 hour endurance to a half marathon plus or an 8 mile course. Choose your loops and enjoy post race food and awards.

Test your limits on this timed trail ultra at Little Bennett Campground with 5 and 9 hour solo and relay options on a scenic 4.4 mile loop. Enjoy aid stations, Altra demos and a post race chili while supporting Montgomery Parks Foundation.

Run a scenic trail 5k or 10k at The Winery at Bull Run with chip timed results, a finisher medal, tech shirt and a complimentary glass of wine. Proceeds support the Manassas Battlefield Trust.

Hit the trail on Feb 14 for the 1781 Brewery 5k and 10k at Wilderness Run, a hilly cross country course with walkers welcome. Enjoy a post race beer or wine, a finisher medal and chip timing while supporting Semper Fi and America's Fund.

Take on scenic river trails at the Paradise Springs 5k and 10k in Clifton VA on February 28, 2026, featuring challenging rocky sections and plenty of elevation. Finish at Paradise Springs Winery with a finisher medal, tech shirt and a compl..

Run a scenic 50 km trail at Hashawha Environmental Center near Westminster MD on Feb 28, 2026, featuring rolling hills, stream crossings and two big loops. Expect runnable single track, ample climbing and warm post race hospitality.

Join the Bigfoot Endurance Trail Race at Rockburn Branch Park in Elkridge on March 1, 2026 with 5 mile, 10 mile and two person relay options on scenic trails. Get a long sleeve shirt, finisher medal, post race beers and support Parkinson's..

Run Wakefield Park's twisty single track and grassy fields at the Spring Backyard Burn Trail Run in Annandale. Choose 5 or 10 mile routes, support a local charity, and enjoy a friendly series with rewards for referrals.

No Man's 50K is a women only trail running challenge in Triangle, VA on Mar 7, 2026, with 50K and 25K options across scenic singletrack loops. Limited entries and stocked aid stations create a supportive, community driven race day.

Take on scenic forest trails at Conway Robinson State Forest with a 5k or two lap 10k, suitable for runners and walkers of all levels. Support the Lost Dog & Cat Rescue Foundation and earn a finisher coin plus a tech shirt.

Run scenic single track trails at Seneca Creek State Park in Gaithersburg March 7, 2026 with the MCRRC Seneca Creek Greenway Trail Marathon and 50K. Finish at the marathon or keep going to earn a 50K medal amid beautiful creekside terrain.

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.

Join the fourth annual Naked Creek Trail Race at Panorama Farms in Earlysville VA. Choose a 25K or 10K through wooded singletrack, creek crossings and Blue Ridge views while supporting local high school cross country.

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..

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..

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.