Trail Running calendar near Leesburg 2025-2026

Blazing Saddles is a scenic trail race at Codorus State Park offering 50K, 25K and 8 mile distances over singletrack and runnable hills with mud and possible snow. Join fellow runners to test yourself and support a local animal rescue.

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.

The Genesee Valley Ultra is an endurance running event held at the Genesee Valley Outdoor Learning Center in Parkton, Maryland. It features a 2.5-mile trail loop through farm roads, grass fields, and some double track on private property. P..

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..

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..

Take on 50 miles of rolling forest trails along the Occoquan River and Bull Run in Clifton, Virginia on April 4, 2026. Enjoy spring bluebells, a Civil War themed route, Trail Sisters approved inclusivity, and a 13 hour time limit.

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..

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 p..

Run 100 miles along the scenic C&O Canal towpath near Knoxville Maryland on April 25 2026, a WSER 2026 qualifier. Smooth, low elevation loops along the Potomac with volunteer staffed aid stations.

Event information The event is a 5k held on April 26, 2026 at Bluemont Station Brewery & Winery in Bluemont, VA (18301 Whitehall Estate Ln). Points from the race count toward the Year-Long 5k & Back of the Pack Series and the Sippin..

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.

The MMT 100 is a demanding 100 mile trail ultra in Virginia's Massanutten Mountains with over 18,000 feet of climbing. On May 16, 2026, tackle this rugged course with a 36 hour cutoff.

Take on the More Miles Last One Standing Challenge on May 30 in Knoxville MD, a backyard ultra where runners cover a 4.167 mile loop each hour until one remains. Prize money, a 1 mile race, and a Backyard Ultra qualifier add the drama.

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This..

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.

Choose the 3H Trail Half or DHRT 50K on the shaded Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026 for a scenic, mostly flat trail experience. Expect a smooth rail bed, custom finisher medal and technical shirt, and br..

Event overview The MD Heat Trail Race is a trail running event at the Patapsco Pickall Area in Elkridge, MD. The event offers the following distances: 50K 25K On-site parking is adjacent to the pavilions and start/finish area at Shelter #..