Trail Running calendar near Leonardtown 2025-2026

Fall Backyard Burn Trail Run - Fountainhead is a trail-running event at Fountainhead Regional Park in Fairfax Station, VA. The race offers two distances: a 5-mile loop and a 10.5-mile course, with elevation gains around 450 feet and 1000 feet, respectively. The 5-mile loop is a classic EX2 single lo..

The Pocahontas Half is a scenic running event held at Pocahontas State Park near Richmond, Virginia. It features a half marathon, 10k, and 5k race, all taking place on the forested Bright Hope Trail, which offers a soft dirt and pine needle surface with some minor hills. The half marathon course is..

The Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain without major hills. Participants enjoy a chip-timed race with..

Founders Half Marathon is a Snowball Series running event held in Potomac, Maryland, at Carderock Recreation Area. It features a USATF-certified, out-and-back 13.1-mile course along the C&O Canal Towpath, with two water stops (Lock 10 and Lock 6) along the route. It is touted as the lowest-priced ha..

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 outdoor Sassafras Pavilion. Historically tied to the Annapoli..

The Snowy Owl 10 Mile is a trail running event held at York River State Park in Williamsburg, VA. The course features a mix of technical single-track trails, dirt fire roads, a short paved downhill finish, and scenic boardwalk sections, covering 10 miles with about 600 feet of elevation gain. Runner..

Chills In The Mill: Harwoods Half Marathon & 5K takes place in Yorktown, Virginia, starting off Oriana Road near Harwoods Mill. The event offers two distances — Harwoods Half and Harwoods 5K — with capped fields (200 for the half, 150 for the 5K). Runners encounter a mix of wide, open trail roads an..

Angela Ivory Memorial Trail Runs is an annual ultramarathon event held at Killens Pond State Park in Felton, Delaware. The race offers three distance options: a 50-kilometer, a 100-mile, and a 24-hour run, inviting endurance athletes to tackle different formats. The next edition is scheduled for Jan..

Located at Rockburn Branch Park in Elkridge, Maryland, the Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon built from six loops of about 5.18 miles through wooded trail terrain. The event also offers a 50k relay, allowing teams of up to six runners to share the distance with exchanges aft..

The Dahlgren Trail Half Marathon, held in King George, Virginia, offers a scenic out-and-back course along the flat, smooth Dahlgren Railroad Heritage Trail. This event features a 13.1-mile race on an old railroad bed, providing a comfortable and picturesque running experience. Participants enjoy ca..

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 Wincopin trails along the Little Patuxent and Middle Patuxent River. Distances..

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 Challenge, 9-Hour Relay, and More Than a 4-Miler, all based on a..

The ICY-8 Spotsylvania Courthouse is an annual trail running event held at Lake Anna State Park in Spotsylvania, Virginia. Featuring an 8-hour adventure trail run and a concurrent half marathon+, the race offers a unique figure-8 course composed of three loops: an 8.0-mile long loop, a 4.7-mile shor..

The Algonquin 50K is a Delmarva Peninsula trail ultramarathon held in Pocomoke City, Maryland, with start and finish at Milburn Landing in Pocomoke River State Park. The approximately 31-mile course is a modified out-and-back on mostly trail, including single-track and wider horse paths. It’s genera..

Paradise Springs 5k & 10k is a trail race at Paradise Springs Winery in Clifton, VA, offering a technical Hemlock Overlook Park course by the river. The 10k is two laps of the 5k route, with substantial elevation changes and a rocky section. Runners receive a finisher medal, technical shirt, a glass..

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 10k consisting of two laps of the 5k route. Walkers are welco..

No Man's 50K is a women-only trail running endurance event held in Triangle, Virginia, featuring 25K and 50K distances. The course consists of two loops of approximately 15 miles each, designed as a great first-time ultramarathon route. Runners experience a mix of terrain with about 70% single track..

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 Pavilion. Runners may complete as many laps as they wish within th..

Capital Backyard Ultra is a Last Runner Standing race held at Meadowood Special Recreation Management Area, 10702 Harley Rd., Lorton, Virginia, near Washington, DC. The course is a 4.167-mile loop that runners complete in succession, with the field reduced until only one remains, who must finish one..

Women's Trail Festival is a trail running and hiking event in Freedom Park, Williamsburg, Virginia, organized by Happy Cat Fitness. The festival features a competitive 10-mile loop on Saturday and a 10-mile hike on Sunday, plus an 8k hike on Saturday that uses the first portion of the course. The lo..