Trail Running calendar near Chesterfield 2025-2026

We have found 34 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

Join RRRC in February 2026 at Bear Creek Lake State Park for Bear Creek 10 Mile and 4.2 Mile Mini Trail Runs, offering in person races plus a virtual 10 Mile option. Tackle scenic single track and multi use trails while supporting the park.

Explore a scenic loop around Saint Marys Lake and Salem Forest with 17K, 34K and 50K options on mostly single track trails and about 500 ft of climb per lap. Limited to 100 runners, with pancakes served at the finish.

March 2026

Run a scenic 3.42 mile loop at Twin Lakes State Park with options from 10 miles to 48 hour solos and relays. Primitive camping, a staffed aid station, and awards like a 100 mile belt buckle create a festive endurance weekend.

Run, learn and connect at the Women's Trail Festival in Williamsburg on March 28 and 29. Choose 10 mile or 8k routes, enjoy a shirt, lunch and finisher medal, and support local charities.

April 2026

Tackle scenic James River Trail at James River State Park in April 2026 with day and night 10 mile runs or multi loop 50K and 50 mile options. Expect steady climbs, riverside flats and on course aid with gluten free options.

Mountain & Vine Vineyard 3k, 6k, & 9k takes place at Mountain & Vine Vineyards in Faber, Virginia (500 Delfosse Winery Ln.). The course loops the winery property: 3k is one lap, 6k two laps, and 9k three laps, delivering a hilly but scenic..

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..

Join Virginia Run for Cancer in Hampton VA, a 24 hour solo and team event on a flat 3.75 mile dirt trail where runners and walkers of all abilities are welcome. Chase team and solo awards while supporting the American Cancer Society.

May 2026

Run the Motion for Justice 5k in Rocketts Landing along the scenic Virginia Capital Trail with James River views. Enjoy a finisher medal and technical shirt or go virtual if you cannot attend in person.

June 2026

Run or hike the Taskinas Creek half marathon on June 7, 2026 at York River State Park in Williamsburg. Scenic trails and rolling hills, with a tough final two miles, make this relaxed Hike a Half a memorable challenge.

Night Train is an evening trail run along the scenic High Bridge Trail in Farmville, VA, offering distances from 5K to 50K plus a family 5K option. Start and finish at Camp Paradise and enjoy a memorable finish across the bridge.

July 2026

Windsor Castle Park hosts a low key, manually timed event on a shaded 3.1 mile loop in Smithfield, VA with 10 hour, 5 hour, 2 hour and 5k options. Stocked aid station, rucking option and handmade finisher items make for a friendly, challeng..

August 2026

Choose the half marathon or 50K on the shaded, flat Dahlgren Railroad Heritage Trail in King George on August 8, 2026. Enjoy fast footing, a finisher medal and tech shirt plus post race food and drinks.

October 2026

Explore scenic new hiking trails at Pocahontas State Park with options of a half marathon or 10k, both starting and finishing on the park's grass field. Pro chip timing and live results add a competitive edge to this fall trail run.