Trail Running calendar near Winchester 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..

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..

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 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..

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..

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. Participants enjoy a challenging yet beautiful run and receive a fini..

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..

The Bull Run Run 50 is a trail race of 50 miles scheduled for April 4, 2026, in Clifton, Virginia. The event is organized by volunteers from the Virginia Happy Trails Running Club and was established in 1993. The listed entry fee is $125 and a 13 hour time limit applies. Registration is planned to..

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. Walkers are welcome, and a virtual race option is available for r..

The Trail Demon 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features a technical forest trail loop with tree roots, rocks, and elevation changes, offering scenic views and a demanding workout. Runners can choose between the 5k or 10k distances..

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 run, offering participants a scenic course winding through a..

Run to Remember in Sykesville, Maryland takes place at Piney Run Park (30 Martz Rd, Sykesville, MD 21784). The event offers multiple distances: 50K (6 loops of 5.25 miles), 25K (3 loops), an 8 Hour Challenge, and a 5.25-mile race. The course runs through woods and meadows with lake views along about..

Barrel Oak 3k & 6k is a cross-country running event at Barrel Oak Winery in Delaplane, Virginia. The course winds through vineyard grounds with gravel sections and rolling hills, and the 6k is two laps of the 3k route. Walkers and leashed pets are welcome.Runners receive a glass of wine, a finisher’..

The C&O Canal 100 is a 100-mile ultramarathon held in Knoxville, Maryland, along the scenic C&O Canal towpath near the Potomac River and Appalachian Mountains. The course features one approximately 40-mile loop followed by two 30-mile loops, starting and finishing at Camp Manidokan. Runners enjoy a..