Trail Running calendar near Shippensburg 2026-2027

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 free 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.

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 re..

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.

Maryland Turkey Trot on November 22, 2026 at Carderock Park in Potomac MD offers 5k and 10k courses with virtual entry options; walkers are welcome.

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.

Thanksgiving Day events at Sherando Park on 11/26/2026 include a 3.1 mile 5K plus a 100 m Tot Trot and two kids fun runs, each with specified registration windows and fees.

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.

A trail-based 5K and 10K in Wheaton Regional Park on November 26, 2026, with in-person and virtual categories and points toward year-long series.

A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.

Black Friday 5k and 10k at Frying Pan Park in Herndon on November 27, 2026, offering in person and virtual options plus onsite farm animals.

A scenic Thanksgiving weekend 5K and 10K at Henway Hard Cider in Bluemont, VA on November 28, 2026, featuring post-race cider and virtual participation options.

Trail races at Governor Dick Park in Mt. Gretna on December 12, 2026 offering 5 mile and 10 mile courses, with all proceeds funding trail and park improvements.

A 13.1 mile out and back on the C&O Canal Towpath at Carderock Recreation Area with online registration, two water stops, live timing, and post-race refreshments.

A night trail run at Zindel Park in McElhattan, PA offering a mostly runnable 7 mile course and a 5K; headlamps required and registration is limited to 250 entrants.

A January running event in Bethesda with 5K, 10K and half marathon courses at Carderock Recreation Area, plus virtual options and series points.

A scenic Potomac River road race in Potomac, MD offering 5K, 10K, half marathon and virtual options with walkers and strollers welcome.

A 50 km trail run at Hashawha Environmental Center in Westminster MD, featuring varied single-track, open fields, stream crossings and 5 aid stations. Entry for 2027 uses a lottery opening January 1, with indoor facilities and hot post-race..

Club-based 10-mile competition at Howard Community College where runners score points for RRCA clubs, with awards by club and a 2h10m cutoff.

In-person 8k and 16k races along the Potomac River and C&O Canal path in Potomac, MD, with virtual options and post-race waterfall views.