Trail Running Calendar Maryland 2025-2026

The Sweet Air Trail Race, organized by the Baltimore Road Runners Club, is a challenging trail run held at Gunpowder State Park in Sweet Air, Maryland. The course spans approximately 8 miles, featuring rolling hills, fast sections, water crossings, and occasional mud, providing a varied and adventur..

The Endless Summer 6-Hour Run, held annually at Greenbury Point Nature Center in Annapolis, MD, is a timed endurance event featuring solo and relay (3-person teams) categories. Participants run a 2.5-mile loop course that includes a scenic stretch onto Possum Point, offering views of the Chesapeake..

The Run the Vineyards Bohemia Manor Farm 5K & 8K is a scenic running event held at Bohemia Manor Farm Winery in Chesapeake City, Maryland. Participants can choose between a 5K run that winds through vineyards, along the Bohemia River, and wooded trails, or a more technical 8K trail run featuring sim..

The Blue Crab Bolt Trail Run at Schaeffer Farms in Germantown, MD, is a trail running event featuring 5K and 10K distances. Held at the scenic Button Farm Living History Center, the course offers a mix of flowy, fast, and fun trails with twisty single-track paths, stream crossings, log ramps, some h..

The Blue Crab Bolt Trail Run at Little Bennett Regional Park in Clarksburg, MD, offers a scenic and challenging trail running experience on August 2, 2025. Set in a 3,600-acre park with over 20 miles of trails, the event features 5K (3.7 miles) and 10K (6.2 miles) races along twisty single-track hik..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running distances of 25K and 50K. The course features rolling single-track trails with over 2,000 feet of elevation gain, two river crossings, and a mix of technical rocky sections and runnable..

The Pemberton 24 is a unique 24-hour endurance running event held at Pemberton Park in Salisbury, Maryland. Participants, either solo or in four-person teams, run multiple 5K races, with a new 5K starting every hour on the hour over a full day. The scenic trail course features an aid station stocked..

The Cancer Warriors 5k is an annual fundraising event held in Bel Air, Maryland, along the scenic Ma & Pa Trail. The 9th edition, scheduled for September 20, 2025, features a 5-kilometer out-and-back course starting at the trailhead near Independent Brewery, which also hosts the post-race afterparty..

The Rick O'Donnell Memorial Ultra Challenge is an annual trail running event held in Mount Airy, Maryland, hosted by the Frederick Steeplechasers Running Club. The 13th edition takes place at Milkhouse Brewery at Stillpoint Farm and features three race options: a 5-mile trail run, a 4-hour challenge..

The Rocky Gap Trail Run, hosted by EX2 Adventures at Rocky Gap State Park in Flintstone, Maryland, offers challenging 25K and 50K ultra-distance trail races, including relay options for teams of 2 or 3. The course features three distinct loops ranging from 4.4 to 6.5 miles, with varied terrain inclu..

The Patapsco Valley 50K is an annual trail running event held at Patapsco Valley State Park near Baltimore, Maryland, with race headquarters at CCBC-Catonsville. The event features two distances: a 50K and a 25K, both available as in-person or virtual races. Runners enjoy a scenic, historic, and wel..

The Fire on the Mountain 50K Trail Race, held in Little Orleans, Maryland within Green Ridge State Forest, offers challenging distances of 50K (about 31.95 miles) and 25K (approximately 16.3 miles). The 50K is an out-and-back course featuring seven aid stations, including a midway "oasis," with a 10..

The Schaeffer Half Marathon and 10K Trail Run, hosted by EX2 Adventures, takes place at the scenic Button Farm in Germantown, Maryland. This event features two distances: a 13.3-mile half marathon and a 6.7-mile 10K+, both offering challenging courses with twisty singletrack trails and wide-open far..

The MCRRC Stone Mill 50 Mile Run is a challenging trail ultramarathon held in Montgomery Village, Maryland. The 50-mile course features scenic routes along the Seneca Greenway and Muddy Branch trails, traversing forested, rolling terrain primarily on single-track dirt paths. Runners encounter small..

The Rosaryville Veterans Day Trail Race, hosted by Annapolis Striders, is an annual trail running event held at Rosaryville State Park in Upper Marlboro, Maryland. The 16th edition in 2025 features two distances: a 50K ultra and a 20K race. Both courses loop around a scenic 9.5-mile single-track per..

The Tuckahoe 25K is an annual trail running event held in Queen Anne, Maryland, featuring a 25-kilometer (15.5 miles) course primarily on single-track and horse trails. The terrain includes runnable hills, some rooty and muddy sections, but is not overly technical, making it suitable for both newcom..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

The Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon held at Rockburn Branch Park in Elkridge, Maryland. The course consists of six loops, each approximately 5.179 miles, winding through wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members, exchanging..

The Algonquin 50K is a challenging ultramarathon held in Pocomoke River State Park, Maryland, on the Delmarva Peninsula. The mostly flat, fast course covers about 31 miles on 95% trail, including single-track and horse paths, with sandy sections and possible standing water adding difficulty. The rac..

The Genesee Valley Ultra is an endurance running event held at the Genesee Valley Outdoor Learning Center in Parkton, Maryland. It features a 2.5-mile trail loop through farm roads, grass fields, and some double track on private property. Participants can choose from 6, 12, or 24-hour race durations..