Trail Running calendar near Chesapeake City 2026-2027

Take on the Sweet Air Trail Race at Gunpowder State Park on July 12, 2026, a scenic out and back with rolling hills, faster stretches, water crossings and a bit of mud. Limited to 100 runners, entry is free and donations are welcome.

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 the Vineyards at Bohemia Manor Farm offers scenic 5K and 8K courses through vineyards, waterfront and wooded trails, chip timed with live results. Finish with refreshments, a souvenir wine glass and an after party on the river.

Join the Summer Sundown Rundown in Kempton, PA for an endurance trail circuit where short laps, shrinking cutoffs, and the last runner to finish the final lap wins. Celebrate with complimentary Bright Path Brewing beer for 21 and over.

Join Montey's Pack Rescue Run 5K at Heebner Park for a fun 5K, a 1 Mile Kids Fun Walk, or a virtual 5K that helps animals in need. Family friendly course with medals and fundraising prizes and 100% of proceeds support local rescue efforts.

Run rugged single track and river crossings at MD Heat Trail Race in Patapsco Pickall, Elkridge MD. Choose 25K or 50K and expect big climbs, technical rock sections, helpful aid stations and a finish with food and beer.

Enjoy a scenic 5K trail or one mile Move As You Please at Thorncroft Equestrian Center’s 70 acre farm in Malvern. Finish with live music, food trucks and pony meet and greets while supporting care for Thorncroft horses.

Celebrate Labor Day at William Heritage Winery with a chip timed 5K on scenic vineyard paths plus one mile and kids races for all ages. Finishers 21 and over get a souvenir glass and a complimentary wine while supporting HEADstrong.

Join the Sasquatch Preservation Trail Run in scenic Seven Valleys, PA on September 12, 2026 for a fun 5K or 10K through rolling trails and forest scenery. Volunteers welcome to help keep this community event running strong.

Choose from a 25K, 40 Mile or 40 Mile relay on scenic mixed terrain at Codorus State Park, featuring lakeshore singletrack, open fields and historic sites. Enjoy a fully stocked aid station, race day picnic and finisher awards.

Join the Kettle Cooker Five & Dime at Glenroy Preserve for scenic loop trails with 5 mile, 10 mile and 25K options over hills, creeks and rocky terrain. Chip timing, aid stations, a soft tee and post race beer make it a great day.

Run the Vineyards at White Horse Winery features 10K, 5K and 1 mile on a flat scenic vineyard course supporting the HEADstrong Foundation. Enjoy a tech tee, souvenir wine glass, live music, wood fired pizza and a glass of wine.

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.

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 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.