Trail Running calendar near Highfield-Cascade 2025-2026

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando..

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..

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.

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..

Event The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series...

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..

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..

Run the Fall Backyard Burn at Lake Fairfax in Reston on Oct 19, 2025. Choose a 5.1 mile lap or 10 mile option on mostly singletrack with roots, rocks and rolling climbs while supporting local nonprofit Homestretch.

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.

Tussey Mountainback Race Weekend : Oct 25–26, 2025 The event takes place at Tussey Mountain Ski and Family Fun Center, 301 Bear Meadows Road, Boalsburg, PA. The weekend features multiple individual races and relay options. A pre-race lunche..

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..

Event The Halloween Horror event on October 26 takes place at Conway Robinson State Forest in Gainesville, VA. Distances offered: 5k 10k Walkers are welcome. A virtual race option is available. Points from the event count toward the 5k, 1..

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.

Event overview The Fall Backyard Burn Trail Run - Riverbend is scheduled for Sunday, November 2, 2025, at Riverbend Park in Great Falls, VA (8700 Potomac Hills Street, Great Falls, VA 22066). The event is produced by EX2 Adventures. Two cou..

Gulliver's Run is an annual fundraising event in Lewisberry, Pennsylvania, held on the trails of Gifford Pinchot State Park. It features a 5k trail run and a 3.5k walk for dogs and their human companions (participants may join without a dog..

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 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 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..

The Barrel Oak Turkey Trot is a pre-Thanksgiving running event held at Barrel Oak Winery in Delaplane, Virginia. It features two race distances: a 3k and a 6k, with the 6k consisting of two laps around a cross-country course that winds thro..