Trail Running calendar near Williamsport 2026-2027

Trail races of 50k and 25k take place in Patapsco Valley State Park on October 24, 2026 with in-person and virtual options. All entrants receive event apparel and a finishers award, and virtual runners have Oct 24 to Nov 24 to complete thei..

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

A roughly 2 mile untimed loop at Camp Anderson on October 24, 2026 where runners, walkers and costumed zombies navigate Zombie Zones and flag belts. Proceeds benefit Tyrone Snyder Public Library and Camp Anderson.

A trail event at Conway Robinson State Forest Park on October 25, 2026, offering 5K and 10K in-person races plus virtual entries with medal and shirt options. 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.

A backyard ultra scheduled for October 31, 2026 at Shawan Downs with repeated 4.167 mile loops. Runners complete as many loops as they can over a 24 to 48 hour period.

A fall trail event in Little Orleans, Maryland offering a roughly 50K and 25K on forest trails with multiple aid stations and official cutoffs. Training runs take place in September and registration opens February 2, 2026.

A charity trail event at Gifford Pinchot State Park featuring a 5k run and a 3.5k walk with dog-focused awards, proceeds supporting canine cancer research, and a free children's dash for ages 10 and under.

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.

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.

Trail races at Rosaryville State Park in Upper Marlboro offer 20K and 50K on a 9.5 mile single track with wooded scenery, aid stations, a nearby drop bag area, and participant limits and time cutoffs.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre-Thanksgiving event at Barrel Oak Winery in Delaplane offering in-person 3K and 6K races plus virtual options with medal and shirt choices; walkers and leashed pets are welcome.

A 5K cross country race at Herring Run Park on November 15, 2026, featuring mixed paved, field and technical single track surfaces. Entry is free and donations are accepted for scholarships and Friends of Herring Run Parks.

A 48 hour out and back ultramarathon inside Sideling Hill Tunnel near Valley-Hi, PA. Runners cover just under 160 miles in repeated 1.3 mile loops in complete darkness while a Toll Ticket system limits exits.

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.

A 5K and 10K held November 22, 2026, on the flat Carderock section of the C&O Canal Towpath in Potomac, MD. Walkers are welcome and virtual options with medals and shirts are available.

A pre-Thanksgiving trail event at The Winery at Bull Run in Centreville, Virginia on November 25, 2026. Offers 5 km and 10 km in-person races plus virtual categories with medal and shirt options.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.