Trail Running Calendar Maryland 2025-2026

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. T..

Rocky Gap 25K, 50K, Relay Trail Run The event takes place on Sunday, October 12, 2025 at Rocky Gap State Park in Flintstone, MD (12500 Pleasant Valley Road, Flintstone, MD 21530). The program offers solo and relay entries for two distances..

Run scenic hilly trails at the Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge at Milkhouse Brewery in Mt Airy. Pick a single loop or tackle the 4 hour or 8 hour ultra challenges while supporting the scholarship fund.

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 ro..

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 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 betwee..

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 compe..

Run the scenic, historic trails of Patapsco Valley State Park at the Patapsco Valley 50K, offering 50k and 25k distances plus virtual options. Enjoy well stocked aid stations, commemorative shirts and unique finisher awards.

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 sett..

Tackle rugged trails and scenic ridgelines at Fire on the Mountain, a challenging 50K with a 25K option in Little Orleans, Maryland. Cooler November air and lively aid stations make this a fall must for adventurous trail runners.

Honor Veterans Day on scenic single track at Rosaryville State Park with Annapolis Striders, choosing 50K or 20K looped courses. Limited to 250 runners, this friendly trail race offers rolling climbs, aid stations, and awards.

Tackle the scenic MCRRC Stone Mill 50 mile trail run through forested single track on the Seneca Greenway and Muddy Branch in Montgomery Village. Enjoy rolling terrain, stream crossings and community spirit on November 8, 2025.

Event The Schaeffer Half Marathon, 10K, 5K Trail Run is held on Saturday, November 8, 2025 at Button Farm Living History Center in Germantown, MD. The event is produced by EX2 Adventures and includes in-person races and virtual options for..

Event overview The Bobcat Trail Run is an 11-mile trail race held in Cunningham State Park in Thurmont, Maryland. The event starts and finishes at the Manor Parking Area near 6709 Cunningham Falls Park Rd. There is no race-day entry. Entran..

Event overview The Tuckahoe 25k takes place on Saturday, November 22, 2025, in Queen Anne, Maryland (13283 Cherry Ln). The race distance is 25k (15.5 miles) on trail terrain. The event is organized by the Centreville Crushers and Algonquin..

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..

The Anniversary Run 15K is the final race in the Annapolis Striders Championship Series, held on the trails of Quiet Waters Park in Annapolis, Maryland. The course is a 15-kilometer trail route with start, finish, and awards staged at the o..

Event The Founders Half Marathon is scheduled for Sunday, December 14, 2025, in Potomac, MD (ZIP 20854). The event is a half marathon of 13.1 miles and is listed as race #2 of the DCRR Snowball Series. Registration is online only; the event..

Event overview The Little Patuxent River Half Marathon & 10K is a trail race weekend in Columbia, Maryland on Jan 31 - Feb 1, 2026. Races start and finish at the Guilford Pratt Truss Bridge on Guilford Road and use the Patuxent and Winc..

Event overview The Mid-Maryland Trail Festival is scheduled for Saturday, January 31, 2026 in Elkridge, Maryland at Rockburn Branch Park, 6145 Montgomery Rd. The event offers the following race options: 50K 50K Relay Registration closes J..