Trail Running Calendar Maryland 2025-2026

The High Rock Mountain Running Challenge is a Cascade, Maryland race starting and finishing at Pen Mar Park (14600 Pen Mar Rd). The course covers about 3.8 miles, including roughly 1.8 miles of ascent to High Rock Overlook before a descent back to the park for the finish. The route offers a pictures..

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

The Cancer Warriors 5k is held in Belair, Maryland, on the Ma & Pa Trail. The in-person event features a simple out-and-back 5k course starting at the Ma & Pa Trail Head near Independent Brewery, with a second stream crossing, a fork near Route 24, and a turnaround near Tollgate Road before returnin..

The Bull Run Reunion Run 2025 is a 3-mile cross country race held in Parkton, Maryland, at Hereford High School. Scheduled for September 20, 2025, this event is part of the Bull Run Cross Country Invitational and is open to all ages. The Reunion Run is the seventh race of the day, offering participa..

The Kellie Thompson Shiley 5k and Family Fun Run is an annual event held at the Terrapin Nature Trail in Stevensville, Maryland, on the scenic Eastern Shore. It features a 5K trail run/walk and a 1-mile fun run for children aged 10 and under. The race honors Kellie Thompson Shiley’s competitive spir..

River's Edge Endurance Challenge takes place in Brunswick, Maryland, centered at Brunswick Middle School and the nearby River's Edge Trail System. The in-person event offers three races: a 5K (3.1 miles), a 3-hour endurance race, and a 6-hour endurance race, all built around a 5-mile loop with about..

The Lake & Leaf Shuffle is a trail running event held at Deep Creek Lake State Park in Swanton, Maryland, typically scheduled in late September to coincide with peak fall foliage. Participants can choose between a 6-mile single loop or a 12-mile double loop on scenic trails, offering a challenging a..

The memorial 5 Mile Trail Run & Ultra Challenge takes place at Milkhouse Brewery at Stillpoint Farm in Mount Airy, Maryland. It offers three ways to test yourself: a 5-mile trail run, a 4-hour challenge, and an 8-hour ultra, all on a hilly, scenic course that features a five-mile loop of farm lanes,..

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 along with relay options for teams of 2 or 3. The course features three distinct loops ranging from 4.4 to 6.5 miles, combining rugged singletr..

Patapsco Valley 50K is an annual ultramarathon held near Baltimore, MD, with race headquarters at CCBC-Catonsville. The in-person event offers a 50k and a 25k, plus virtual options, set on a scenic, historic, well-marked trail course through Patapsco Valley State Park. The race features five aid sta..

RTB Fair Winds 5k/Fun Run is held at Quiet Waters Park in Annapolis, Maryland. The event offers a 5K, a Fun Run, and a Virtual 5K/Fun Run option. Runners traverse a fully paved course through woods and meadows, presenting a scenic park setting.The atmosphere is upbeat and community-minded, with cost..

Fire on the Mountain 50K Trail Race takes place in Green Ridge State Forest near Little Orleans, Maryland. The event offers a 50K (about 31.95 miles) and a 25K (about 16.3 miles) on a mix of trail, forest roads, and dirt roads. The 50K is out-and-back with seven aid stations (three hit twice) and an..

The MCRRC Stone Mill 50 Mile Run is a 50-mile trail ultramarathon in Montgomery Village, Maryland, organized by MCRRC. The course uses forested, rolling terrain along the Seneca Greenway and Muddy Branch trails in Montgomery County, primarily on single-track dirt trails with small stream crossings...

EX2 Adventures’ Schaeffer Half Marathon and 10K Trail Run takes place at Button Farm Living History Center in Germantown, MD, on Schaeffer Farms. The course features Schaeffer’s renowned twisty singletrack and open farm-field segments, offering a rugged mix for trail runners. Distances include a hal..

Rosaryville Veterans Day Trail Race, held in Rosaryville State Park in Upper Marlboro, Maryland, offers 50K and 20K trail distances on wooded perimeter single-track trails. The course features rolling hills with about 2,600 feet of elevation gain, mostly through deep woods and meadows, with scenic v..

The Tuckahoe 25k is a trail race in Queen Anne, Maryland. It covers 25k (about 15.5 miles) on mostly single-track trails with some wider horse trails. The course is not overly technical but includes runnable hills, rooty, muddy sections, and varied conditions.Runners can expect three fully stocked a..

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..

Located at Rockburn Branch Park in Elkridge, Maryland, the Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon built from six loops of about 5.18 miles through wooded trail terrain. The event also offers a 50k relay, allowing teams of up to six runners to share the distance with exchanges aft..

Froggy Hollow 5 & 9 presented by Altra is a Charm City Run signature trail ultra held at Little Bennett Campground in Clarksburg, Maryland, inside Little Bennett Regional Park. The event includes 5-Hour Challenge, 5-Hour Relay, 9-Hour Challenge, 9-Hour Relay, and More Than a 4-Miler, all based on a..

The Algonquin 50K is a Delmarva Peninsula trail ultramarathon held in Pocomoke City, Maryland, with start and finish at Milburn Landing in Pocomoke River State Park. The approximately 31-mile course is a modified out-and-back on mostly trail, including single-track and wider horse paths. It’s genera..