Virginia
Virginia Trail Running Calendar 2026-2027
Explore the best trail runs in Virginia for 2026-2027! Our updated list features 143 exciting trail runs across the region. Find your next trail run in Virginia below and join the trail community at these great events!
October 2026
An obstacle course weekend at Massanutten Resort on October 24 and 25, 2026 featuring 5 km and 10 km races plus kids events and spectator access.
Last person standing backyard ultra at Teventrails in Earlysville, VA where runners must complete a 4.17 mile loop each hour.
A 24-hour endurance event at Greensprings Interpretive Trail in Williamsburg supporting The Arc of Greater Williamsburg, where participants aim for distances like a marathon or 50 miles.
Night trail run on October 24, 2026 through Explore Park covering 3.6 miles on marked single track; a light source is mandatory and registration fees vary by date.
Fundraising trail event in Crozet with 5K, 10K and a 0.75 miles family run, limited fields, race shirts, pancakes and a post-race trails fest.
A cross country 5K at Verdun Adventure Bound in Rixeyville with proceeds supporting recovery programs and on-site family activities and awards.
A family friendly school fundraiser in Irvington offering a grassy 5K on the Lancaster High cross country course and a 1 mile fun run.
A trail 5k and 10k at Conway Robinson State Forest with chip timing, finisher medal, technical shirt, water stations, and a virtual option.
A trail half marathon at First Landing State Park with sandy, rooty trails, about 300 feet of climbing, included shirt and beanie, and a four hour time limit.
Halloween-themed 5k and 10k at Indian Fields Tavern/5 Fields Brewing Co. with costume judging, official timing, finisher medal and a finish-line beer.
Motion for Justice 5K in Rocketts Landing, VA on October 31, 2026, is a scenic 5K along the Virginia Capital Trail with views of the James River.
A 5k and 10k at Burke Lake Park on mostly paved trails, with a virtual option, chip timing, race shirts and medals, and proceeds supporting The Brain Foundation housing program.
Trail races at Pandapas Pond with 12 mile, 7 mile and 5K options on single track trails, creek crossings, and varied aid station support.
A Halloween 5K run/walk at Pamplin Historical Park on October 31, 2026, with a costume contest and age-category awards.
Boydton Day Boo Bash 5K on October 31, 2026 is a trail out and back run and walk with a costume contest; all proceeds support the Mecklenburg County Cancer Association.
November 2026
A 24 hour ultra at Riverside Park in Lynchburg, VA that uses a single 0.84 mile paved loop. Runners can enter solo or as a team and compete over a published 100 Miles distance while passing the same start and aid area each lap.
A timed, non competitive trail event at Wintergreen offering 7, 14, 21 and 28 mile loop options. Participants can add weighted vests, face a 10 hour cutoff for awards, and expect on site parking and finisher items.
November 7, 2026 races on the Chessie Nature Trail in Virginia including marathon, half, 10K, 5K and a 26.2 relay on a flat gravel and grass rail trail.