Trail Running Calendar Maryland 2025-2026

The Pemberton 24 is a unique running event taking place in Salisbury, MD, where participants can run as many 5k races as they wish over a 24-hour period. Starting on September 19, 2025, runners will embark on a new 5k every hour, with the course set in the scenic Pemberton Park trail system. The eve..

The Cancer Warriors 5k is an annual running event dedicated to raising funds and awareness for cancer research. Scheduled for September 20, 2025, this event has successfully raised over $38,000 to support those affected by cancer. Participants can register as runners or "ghost runners," allowing ind..

The Rocky Gap Trail Run features a challenging 25K and 50K race, along with a relay option, set in the scenic Rocky Gap State Park in Flintstone, Maryland. Participants can experience three distinct loops, showcasing the park's natural beauty and varying terrain. The 25K consists of one loop, while..

The Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge is an annual running event held in Mount Airy, Maryland, organized by the Frederick Steeplechasers Running Club. The event features three distinct challenges: a 5-mile trail run, a 4-hour challenge, and an 8-hour ultra challenge, allow..

The Patapsco Valley 50K is an annual trail running event held in Patapsco Valley State Park, Maryland, featuring both a 50K and a 25K race. Participants can choose to run in-person or virtually, with the virtual option allowing runners to complete their distance anytime between October 25 and Novemb..

The Fire on the Mountain 50K Trail Race, taking place on November 2, 2025, in Little Orleans, MD, offers both 50K and 25K race options. The 50K course features approximately 31.95 miles with seven aid stations, while the 25K covers about 16.3 miles with three aid stations. Participants must complete..

The Rosaryville Veterans Day Trail Race, hosted by the Annapolis Striders, is a celebrated annual event taking place at Rosaryville State Park in Upper Marlboro, Maryland. This year marks the 15th edition of the race, featuring both 50K and 20K distances. The course offers a scenic and challenging e..

The Schaeffer Half Marathon and 10K Trail Run, organized by EX2 Adventures, takes place at the scenic Button Farm in Germantown, MD. This event features a challenging course known for its twisty singletrack and open farm fields, offering participants a unique running experience. The half marathon co..

The MCRRC Stone Mill 50 Mile Run is a challenging trail running event set in Montgomery County, Maryland, showcasing the scenic Seneca Greenway and Muddy Branch trails. Participants navigate a primarily single-track dirt course featuring forested, rolling terrain and small stream crossings. The even..

The Tuckahoe 25K is an exciting trail running event scheduled for November 22, 2025, in Queen Anne, MD. This race, organized by the Centreville Crushers and Algonquin Ultras Inc., offers a challenging yet accessible 25K course primarily on single-track and wider horse trails. Participants can expect..

The 21st Annual Catonsville High School XC Turkey Trot is a cherished community event celebrating health and wellness. Scheduled for November 27, 2025, this event features a 1 Mile Family Fun Run and a 5K race, both of which are chip-timed. Participants can enjoy a family-friendly atmosphere while s..

The Mid-Maryland Trail Festival 50k is an exciting running event taking place in Elkridge, MD, featuring a challenging 31-mile course comprised of six loops through scenic wooded trails. Participants can choose to run the entire 50k solo or form relay teams of up to six members to share the distance..

The Algonquin 50K is a trail running event taking place in Pocomoke City, MD, on February 7, 2026. This race offers a flat, fast course ideal for both first-time ultra runners and those seeking a competitive time. The route is primarily on trails, featuring a mix of single track and wider horse trai..