Trail Running Calendar Maryland 2025-2026

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 is a nonprofit running event held at Brunswick Middle School, Maryland. The lineup includes a 5K (3.1 miles), a 3-Hour Endurance Race, and a 6-Hour Endurance Challenge. The largely trail-based course runs on the River's Edge Trail System, with about a mile on school..

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..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. The course is a natural trail through the park, with water st..

The Rick O'Donnell Memorial 5 Mile Trail Run & Ultra Challenge takes place at Milkhouse Brewery at Stillpoint Farm in Mount Airy, Maryland. In its 13th year, the event offers three ways to test endurance: a single 5-mile trail loop, a 4-hour challenge, and an 8-hour ultra challenge. The hilly course..

Rocky Gap 25K, 50K, and Relay Trail Run takes place at Rocky Gap State Park in Flintstone, Maryland, in the mountains of western Maryland. The course uses three loops—Loop A (6.5 miles), Loop B (4.4 miles), Loop C (5.2 miles). The 25K runs each loop once (about 16 miles); the 50K runs them twice (ab..

Boulder Dash at Pinesburg Quarry is a running event hosted by Martin Marietta in Williamsport, Maryland. It offers a 5 Mile Challenge, a Family Friendly 5K, and a 1 Mile Fun Run for all levels. The 1 Mile Fun Run and 5K travel on rolling roads and packed gravel around the quarry; the 5 Mile goes int..

Coastal Walk & 5K Run is a charity running and walking event held at Assateague State Park in Berlin, Maryland, located at 6915 Stephen Decatur Highway. Organised to support Coastal Hospice, it offers two options: a Coastal Hospice 5K Run and a Coastal Hospice 2 Mile Walk. The 5K course starts on a..

Located in Bel Air, MD (Ma and Pa Heritage Trailhead), The Husky Run 5K is a community-focused running event along the scenic Ma and Pa Trail. The 5K is designed for all levels—perfect for beginners, comeback runners, and everyone in between—offering a Sofa to 5K Walk & Run. Participants can expect..

North Point Fright Night 5K & Haunted Trail is a Halloween-themed community event at North Point High School in Waldorf, Maryland, on October 25, 2025. The day features a 5K on the school’s official cross-country course (certified for competition) with three race waves: Elite, Middle School & Younge..

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..