Hillsboro
Trail Running Calendar near Hillsboro 2026-2027
Explore the top trail runs near Hillsboro for 2026-2027! We've gathered 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A trail 5k and 10k at Conway Robinson State Forest with chip timing, finisher medal, technical shirt, water stations, and a virtual option.
Scenic 5K through vineyards and farm at Rocklands Farm Winery with chip timing, post run wine options, live music, and awards for overall and age group finishers.
November 2026
Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.
Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.
Community 5K and 1-mile kids run at Clarke County Parks & Recreation with chip timing, course support, awards, a food drive, and door prizes.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A November event in Brunswick MD with a full marathon, half marathon, and a Veterans Challenge 5K that features towpath running, river crossings, and historic town sections.
A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are requested.
Half marathon, 10K and 5K on the C&O Canal towpath from Great Falls Tavern on Nov 21, 2026 with live tracking, a capped field, and scratch made donuts and pizza at the finish.
Trail race at Riverbend Regional Park near the Potomac offering 5 mile and 10 mile loop options with riverside singletrack, aid stations, and post race food.
A trail 5k and 10k at Winery at Bull Run through Manassas National Battlefield with in-person and virtual options.
Thanksgiving Day event in Stephens City VA featuring a 5K plus kids fun runs and a Tot Trot with set registration windows and no race day registration.
A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.
Thanksgiving 5k and kids races at James Rumsey Technical Institute supporting local backpack programs and youth initiatives.
December 2026
Timed trail ultra on 12/05/2026 at Little Bennett Regional Park with 5 hour and 9 hour formats, relays, and a 4.5 mile race.