Trail Running calendar near Holtwood 2026-2027

Scenic trail running at Milkhouse Brewery in Mount Airy with a 5 Mile race and 4 Hour and 8 Hour ultra challenges. Presented by the Frederick Steeplechasers to honor Rick O'Donnell and raise funds for local scholarships.

Scenic lake loop trail runs at Lums Pond State Park offer everything from a single lap 12 KM to a 24 KM and 12 hour solo or 4 person relay. Aid stations and race day bib pickup make it a relaxed fall challenge.

Experience scenic, historic trails of Patapsco Valley State Park with the 50K and 25K on Oct 24, 2026, offering in person and virtual options. Finishers earn special swag including a hand thrown mug for 50K completers.

Run the mostly flat, fast lollipop loop at Parvin State Park in the Hot Mess Trail Races, offering a Half Marathon or a 6 hour lap event. This cupless race asks runners to carry their own cup and pack out trash.

Run Schaeffer Farms singletrack in Germantown on Saturday, November 7, 2026 with half marathon, 10K and 5K options. In person and virtual entries welcome; proceeds support Interfaith Works for a fun, challenging trail day.

Forbidden Run Fest takes runners through scenic Wissahickon Valley Park with 10K, 10 mile and half marathon options on gravel, dirt and single track trails. Limited to 750 entries, all finishers get a medal and sweatshirt and enjoy post rac..

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run a rugged 25k through scenic single track and horse trails in Queen Anne, Maryland on November 21, 2026. Expect runnable hills, muddy rooty sections, three stocked aid stations, and a lively race vibe with swag and awards.

Run Thanksgiving at the 22nd Catonsville High School Turkey Trot featuring a chip timed 5K and 1 Mile Family Fun Run on a cross country course. Proceeds support CHS cross country and there are prizes; strollers and pets not allowed.

Run a festive 5K trail through Autumn Lake Winery on Thanksgiving Day in Williamstown, NJ, with trails, grassy and sandy stretches and no time limit. Family and dog friendly, with proceeds benefiting Lucky Paws Animal Assistance.

Celebrate the season at Milford Reindeer Stampede 5k at Killens Pond State Park on November 28 with a scenic run or competitive walk. Enjoy a long sleeve race shirt, post race treats and chip timing in this family friendly holiday event.

Take on The Naked Nick at Blue Marsh Lake in Leesport, PA on Dec 13, 2026 with 25K and 50K options over scenic singletrack and gravel trails. Expect rugged winter conditions, mid race aid and hearty post race food and awards.

Frosty Looper is on December 13, 2026 at Cooper River Park in Pennsauken, NJ, on a fast flat 3.75 mile loop with Philly skyline and lake views. Presented by HOKA, expect race swag, a stocked aid station and an 8 Hour challenge.