Leesburg
Trail Running Calendar near Leesburg 2026-2027
Explore the top trail runs near Leesburg for 2026-2027! We've gathered 57 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.
Trail 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; walkers are welcome.
Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.
Scenic 5 km and 10 km races through Burke Lake Park on October 31, 2026, with in-person and virtual entry options; walkers and strollers are welcome.
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.
Trail 5 km and 10 km races at Burke Lake Park on November 7, 2026, with walkers welcome and virtual entries offering medal and shirt options.
Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.
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.
Experience riverside singletrack at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.
In-person 5 km and 10 km races on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD, with virtual entry options on November 22, 2026.
A 5 km and 10 km race at The Winery at Bull Run in Centreville on November 25, 2026, with in-person and multiple virtual entry options.
Thanksgiving morning run at Burke Lake Park offering 5K and 10K courses plus virtual options and a technical shirt guaranteed for registrations before November 13.
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.
Trail 5K and 10K in Wheaton Regional Park on November 26, 2026, with virtual options and series points for year-long and fall standings.