Trail Running calendar near Keswick 2025-2026

Run the Valley View Mike Donahue Memorial 5 Miler at Hydaway Outdoor Center in Lynchburg for scenic single track and mountain road trails. A virtual option lets you join the Fall Liberty Mountain Trail Series from anywhere.

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 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.

Fall Backyard Burn Trail Run at Laurel Hill offers 5.4 and 10 mile trail options through scenic forest and meadow at the Workhouse Arts Center. Family friendly with a kids race and a charity partnership benefiting Homestretch.

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 the 30th Chesterfield Alumni Run on Thanksgiving at Pocahontas State Park with a free community XC 5k and kids fun run with gingerbread cookies. Stay for giveaways and optional donations to support local track and cross country.

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.

Run the scenic High Bridge Trail in Farmville on December 6 with options from half marathon to a challenging 100k. Flat rail trail, aid stations, finisher awards and a friendly small race vibe for newcomers and ultrarunners.

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..

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.

Run the Freight Train on Saturday December 6 2025 in Farmville Virginia, with distances from half marathon to 100K on a scenic rail trail. Cross the iconic High Bridge twice and earn a handcrafted pottery finisher award.

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..

Run the Pocahontas 5k, 10k or half marathon on Dec 13 along the scenic Bright Hope Trail in Pocahontas State Park. Walkers and virtual runners welcome with chip timing. Finishers get a coin and shirt and proceeds benefit Operation Turbo.

Join Dash through the Hills on Dec 13, 2025 at Hardware Hills Vineyard for a scenic charity trail 5K or 1.1 mile walk benefiting Caring for Creatures animal sanctuary. Finish at the tasting room with live music, a food truck and wine for pa..

Join Willis River on Jan 4, 2026 at Bear Creek Lake State Park for free 20K, 35K and 50K trail runs. Expect stream crossings, rolling hills and wet, rugged trail on a friendly, casual fat ass style event with shared packaged snacks.

Hit the trails on January 10, 2026 in Palmyra VA for the Burke Creek Barn Burner, offering 5K and 15K trail distances. Enjoy on site coffee, finish line food and awards for a fun community race organized by the CATs.

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 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.

Take on the Arctic 5k on February 7, 2026 at Hydaway Outdoor Center in Lynchburg VA, a 3.1 mile trail run over single track and forest roads. Part of the Liberty Mountain Trail Series, it features awards, a guaranteed giveaway t shirt for e..