Trail Running calendar near Stephens City 2025-2026

The Laurel Highlands Ultra - Fall Classic is a challenging 50K trail race held in Somerset, Pennsylvania, along the scenic Laurel Highlands Hiking Trail. The 2025 event features a point-to-point course starting at Laurel Summit State Park and finishing at Rt 56 in Seward, showcasing rugged terrain w..

The Brandy Station Battlefield race offers road and trail running options at Brandy Station Battlefield, Brandy Station, VA. The organizer stages both an in-person event and a virtual run option. Points from the event count toward the 5k, 10k, Back of the Pack Series, and the Summer Series. Distanc..

The Lake & Leaf Shuffle is a trail running event held at Deep Creek Lake State Park in Swanton, Maryland, typically scheduled in late September to coincide with peak fall foliage. Participants can choose between a 6-mile single loop or a 12-mile double loop on scenic trails, offering a challenging a..

River's Edge Endurance Challenge is a nonprofit running event held at Brunswick Middle School, Maryland. The lineup includes a 5K (3.1 miles), a 3-Hour Endurance Race, and a 6-Hour Endurance Challenge. The largely trail-based course runs on the River's Edge Trail System, with about a mile on school..

Run to the Taproom - Creekside Farm Brewery 5K & 8K takes place at Creekside Farm Brewery in King George, Virginia. The event offers scenic 5K and 8K courses on a well-maintained dirt trail through a 1,000-acre farm bordering the Rappahannock River. It is chip-timed with awards for Top 3 Overall and..

The event takes place on September 28 at Merrie Mill Farm & Vineyard in Keswick, VA (594 Merrie Mill Farm). It offers two distances: 5k - one lap on a cross-country course with hills, gravel and paved sections. 1 mile - a short cross-country option on the winery property. A virtual run option..

Hauser Hill Spiked Apple 5k takes place in Biglerville, Pennsylvania at the Hauser Hill Event Center, a 172-acre ridge-top venue in apple country. The chip-timed 5K Run/Walk starts and finishes at the winery on a cross-country course with uneven footing and gentle inclines, offering vineyard views a..

Quantico 24-Hour Walk, Run & Relay for Charity is held in Quantico, Virginia, benefiting Semper Fi & America's Fund, which supports wounded service members and military families. The event invites walkers, runners, and relay teams to cover mileage by doing laps or jogging several miles, with team an..

The Fall Harvest 5k is a scenic trail race held at Claude Moore Park in Sterling, Virginia. Set amidst the vibrant colors of autumn, the course features forest paths and leaf-covered trails, offering a picturesque experience for both runners and walkers. This event is part of the Run Your PRCS Parks..

Howlin' Coyote Canicross Trail Race, held in King George, Virginia (11617 Caledon Rd), offers two canicross options: a 10K Canicross and a 1-mile Wild Pup. This dog-friendly, non-profit event is part of the Friends of Caledon State Park series and supports natural resources and educational programmi..

The West Virginia Trilogy is a three-day stage race on and around Spruce Knob, on the Eastern Continental Divide. It takes place over Columbus Day weekend, October 10–12, 2025, and is hosted by the West Virginia Mountain Trail Runners with race headquarters at the Spruce Knob Mountain Center’s 400-..

The Full Distance 5k & 10k takes place on October 11 at Locust Shade Park. Points from the event count toward the Year-Long 5k, 10k and Back of the Pack Series and the Sippin Series. A virtual race option is offered. Walkers are welcome. Distances: 5k 10k Registered participants receive a fin..

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando Park Mountain Bike Trails. Runners experience beautiful fal..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. The course is a natural trail through the park, with water st..

Rocky Gap 25K, 50K, Relay Trail Run takes place at Rocky Gap State Park in Flintstone, Maryland. The race features three scenic loops—Loop A (Rocky Trail, 6.5 miles), Loop B (Canyon Overlook, 4.4 miles), Loop C (Lakeside Loop, 5.2 miles). The 25K covers A–B–C once (about 16 miles); the 50K covers al..

The Rick O'Donnell Memorial 5 Mile Trail Run & Ultra Challenge takes place at Milkhouse Brewery at Stillpoint Farm in Mount Airy, Maryland. In its 13th year, the event offers three ways to test endurance: a single 5-mile trail loop, a 4-hour challenge, and an 8-hour ultra challenge. The hilly course..

Boulder Dash at Pinesburg Quarry is a running event hosted by Martin Marietta in Williamsport, Maryland. It offers a 5 Mile Challenge, a Family Friendly 5K, and a 1 Mile Fun Run for all levels. The 1 Mile Fun Run and 5K travel on rolling roads and packed gravel around the quarry; the 5 Mile goes int..

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a 10-mile quarter loop (Hemidemibivanna), or a 40-mile biking..

The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series. A virtual run option is available. Walkers and strollers are wel..

The event takes place on October 18 at Wilderness Run Vineyard in Spotsylvania, VA (11109 Plank Rd; GPS 38.325153, -77.719921). It features cross country trail courses with hills. The 5k is an out-and-back once and the 10k is two laps of the 5k. Points count toward the 5k, 10k and Back of the Pack..