Trail Running calendar near Winchester 2025-2026

The Winery at Bull Run Turkey Trot offers a scenic trail 5k and 10k through the Manassas National Battlefield Park, starting and finishing near The Winery at Bull Run in Centreville, VA. The course is a cross-country style route across batt..

Join the 21st Annual Catonsville High School Turkey Trot on Thanksgiving morning for a family friendly 1 Mile fun run and a competitive chip timed 5K in Catonsville, Maryland. All proceeds support the CHS cross country program.

The Lake Anna Turkey Trot Half is a scenic and challenging running event held at Lake Anna State Park in Spotsylvania, Virginia. It features three race distances: a 5k trail run, a 10k that is half trail and half paved road, and a half mara..

Event overview Devil Dog Ultras takes place at Prince William Forest Park (Cabin Camp 5) in Triangle, VA on December 6, 2025. The event offers the following distances: 100-Mile 100K 50K Entry is limited to 300 runners. Time limits are 32..

Tackle scenic trails around Occoquan Reservoir at Fountainhead Regional Park in Fairfax Station, VA. Pick a shorter loop or a longer course for a rewarding fall trail challenge, with aid stations and post race food.

Event The Founders Half Marathon is scheduled for Sunday, December 14, 2025, in Potomac, MD (ZIP 20854). The event is a half marathon of 13.1 miles and is listed as race #2 of the DCRR Snowball Series. Registration is online only; the event..

The Anniversary Run 15K is the final race in the Annapolis Striders Championship Series, held on the trails of Quiet Waters Park in Annapolis, Maryland. The course is a 15-kilometer trail route with start, finish, and awards staged at the o..

Event overview The Little Patuxent River Half Marathon & 10K is a trail race weekend in Columbia, Maryland on Jan 31 - Feb 1, 2026. Races start and finish at the Guilford Pratt Truss Bridge on Guilford Road and use the Patuxent and Winc..

Event overview The Mid-Maryland Trail Festival is scheduled for Saturday, January 31, 2026 in Elkridge, Maryland at Rockburn Branch Park, 6145 Montgomery Rd. The event offers the following race options: 50K 50K Relay Registration closes J..

Patriotic Pursuit at Williamsport Park offers 5k, 10k and half runs along a flat scenic C&O Canal Trail beside the river. Chip timed with finisher medal, tech shirt and virtual option supporting Semper Fi & America's Fund.

Froggy Hollow 5 & 9 presented by Altra is a Charm City Run signature trail ultra held at Little Bennett Campground in Clarksburg, Maryland, inside Little Bennett Regional Park. The event includes 5-Hour Challenge, 5-Hour Relay, 9-Hour Chall..

Event overview ICY-8 is a trail running event held at Lake Anna State Park in Spotsylvania, VA. The event includes a concurrently held ICY-8 HALF MARATHON+. The half marathon+ requires participants to complete three loops from largest to sm..

Event overview The 2026 Paradise Springs 5k & 10k takes place on February 28, 2026 at Paradise Springs, 13219 Yates Ford Rd, Clifton, VA. The event is organized by Bishops Events and points from the races count toward the year-long 5k,..

The Winter Conway Robinson 10k is a trail running event held at Conway Robinson State Forest Park in Gainesville, Virginia. The race features a scenic loop course through forest trails with some technical terrain and minor hills, with the 1..

The Dark Side 8 Hour Ultra is an eight-hour trail race at Little Bennett Park in Montgomery County, Maryland, near Clarksburg. The course is a 5.5-mile loop run mostly on single-track trails, starting at the Little Bennett Campground Pavili..

No Man's 50K in Triangle, VA is a women only trail running event offering 50K and 25K loop options through scenic single track and forest roads. Enjoy fully stocked aid stations and a supportive, challenging day on the trails.

The MCRRC Seneca Creek Greenway Trail Marathon will take place in North Potomac on Saturday 7 March 2026. You can run between 42 and 50 kilometers.

Join the Smoketown Brewery 5k and 10k on March 8 for flat gravel out and back routes, with a virtual option and walkers welcome. Finishers get a medal, tech shirt, chip timing and a beer while supporting Wear Blue Run to Remember.

The Twisted Oak 8k is a cross-country running event held at Twisted Oak Farm Brewery in White Post, Virginia. The course features scenic views around the brewery property with minimal hills, where the 8k race consists of two laps. Participa..

Test your grit at the Capital Backyard Ultra, a Silver Ticket last runner standing race at Meadowood near Washington DC. Hourly loops repeat until one runner remains; field is limited to 60 and the winner takes home $1,000.