Trail Running calendar near Middleburg 2025-2026

Run through the vineyards at Barrel Oak Winery in Delaplane VA on November 15 with 3k and 6k options on a rolling cross country loop. Finishers enjoy a glass of wine, a medal and tech shirt plus chip timing and awards.

Join a friendly group run along the Festivus loop on Middleburg's Sandridge Trail. This 7.2 mile course preview offers a welcoming community pace and a great way to learn the route and meet fellow runners.

Join the Fall Backyard Burn at Hemlock Overlook for scenic trail running along Bull Run with roots, rocks and stream crossings. Choose 5.2 or 9.5 miles and enjoy aid stations, race swag and a lively finish.

Join the Freeze Your Gizzard 5K or 1 Mile on Nov 22 at Ida Lee Park in Leesburg for a scenic but challenging cross country course and lively community vibe. Pre registered 5K runners receive a long sleeve shirt and the event supports Loudou..

Event details The 2025 Herndon Turkey Trot is a cross-country style 5K held on November 22 at the Herndon Community Center, 814 Ferndale Ave., Herndon, VA. The race is open to participants age 4 and up. Runners must complete the 5K in 45 mi..

Hit rugged singletrack at Hex Hollow Half in Glen Rock PA on Nov 23, 2025 with a half marathon or 6.66 mile loop. Early registrants get an anniversary tee and proceeds benefit Olivia's House Grief & Loss.

Run a scenic fall trail through Manassas National Battlefield from The Winery at Bull Run with 5k and 10k options, in person or virtual. Enjoy a postrace glass of wine and a finisher medal while supporting the Manassas Battlefield Trust.

Celebrate Thanksgiving at the 21st Annual Catonsville High School XC Turkey Trot with a cross country style 5K and 1 Mile Family Fun Run in Catonsville, Maryland. Proceeds support the CHS cross country program.

Celebrate Thanksgiving at the Lake Anna Turkey Trot on November 28, 2025 at Lake Anna State Park. Run a 5k, 10k or half marathon on scenic trail and road courses with a tech shirt, finisher medal and chip timing, or join virtually.

Devil Dog Ultras in Prince William Forest Park offers 50K, 100K and 100 mile trail loops on well marked single track and rolling fire roads. Expect staffed aid stations, limited bunkhouse beds and a lively winter ultrarunning weekend.

The Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm tr..

Trail run at Fountainhead Regional Park around the Occoquan Reservoir with a 4.8 mile loop and a 10.5 mile option. EX2 Adventures provides on course aid, post race food and swag and a kids race supporting Homestretch.

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 wit..

Enjoy a scenic 13.1 mile run along the C&O Canal Towpath at the Founders Half Marathon in Potomac, part of the DCRR Snowball Series. Friendly on course support and post race snacks make this a welcoming community event.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

Celebrate the season at the Holiday 4 Miler in mid December at Lake Accotink Park in Springfield. Run a scenic loop on paved and dirt trails along the CCT, with in person and virtual options.

Join the Food for Others 5k and 10k at Leesylvania State Park on Jan 17, 2026 for scenic trail and paved sections, small hills, and a festive finish with tech shirts and medals. Proceeds benefit the charity and a virtual option is available..

Run the Mid Maryland Trail Festival at Rockburn Branch Park in Elkridge, MD, a scenic 50K on wooded trails made up of six loops of about 5.18 miles each. Solo runners or teams up to six can tackle the full distance or share loops in a relay..

Run the Dahlgren Trail Half Marathon in King George VA on January 31, 2026. Flat, smooth former railroad bed, aid stations and a custom finisher medal while supporting local trail volunteers.

Patriotic Pursuit at Williamsport Park offers 5k, 10k and half runs along a flat scenic C&O Canal Trail beside the river. Chip timed with finisher medal, tech shirt and virtual option supporting Semper Fi & America's Fund.