Trail Running calendar near Leonardtown 2025-2026

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 The Algonquin 50K takes place on Saturday, February 7, 2026, in Pocomoke City, Maryland. The race is a volunteer-run, non-profit trail event organized to support and expand trail access on the Delmarva Peninsula in collaboration with..

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,..

Explore the Saint Marys Lake Trail Series near Leonardtown MD on Feb 28, 2026, with 17K, 34K and 50K options around a scenic 10.5 mile loop. Limited to 100 runners, this supported trail race features marked routes, aid stations, timing and..

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.

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.

Join the Women's Trail Festival at Freedom Park in Williamsburg for scenic 10 mile and 8k trail runs, fitness classes, talks, lunch and a social with wine and beer. Community focused with awards for competitive races and proceeds benefiting..

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walke..

Run a 50 mile trail race at Hemlock Overlook Regional Park, following the Occoquan River and Bull Run through rolling forest and long bluebell stands. The event blends local Civil War history with a Trail Sisters approved, inclusive vibe an..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun r..

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no..

Run to Remember at Piney Run Park features scenic 5.25 mile loops through woods, meadows and lakeside views, with distances from a 5 Miler to a 50K. Take on the 8 Hour Challenge, earn finisher swag, and support youth programs and cancer res..

Run scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.

Join a no frills Hike a Half half marathon on scenic York River State Park trails, welcoming all paces. Limited to 250 spots, expect rolling single track, a tough final two miles, on course aid, and optional finisher medals.

Run under the stars in Prince William Forest Park on a rugged 25 mile loop once for 25 miles or twice for the 50 mile night challenge. Singletrack trails, stocked aid stations, and limited crew and pacer support.

Event overview The 3H Trail Half Marathon + DHRT 50K is scheduled for Saturday, August 8, 2026, in King George, VA (4224 University Drive, 22485). The event features two races: 3H Trail Half Marathon Dahlgren Heritage Rail Trail 50K Regis..