Trail Running calendar near Annapolis 2026-2027

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

An 8K cross country run at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The mixed terrain course loops through grapevines and hop yards and finishers receive a complimentary tasting.

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

Run through the vineyards at Barrel Oak Winery on this pre Thanksgiving cross country course. The event features a 3k and 6k race, with participants receiving a finisher's medal, tech shirt, and a post race drink. The race supports Warriors..

The Tuckahoe 25k in Queen Anne, MD on November 21, 2026 is a 25 kilometer trail race featuring mostly single track, runnable hills, and some muddy sections. Three stocked aid stations support runners and awards go to the top three men and w..

A trail race at Riverbend Regional Park on November 22, 2026 offering 5 mile and 10 mile routes on riverside singletrack with aid stations, post-race food, parking, and a kids program.

A 5K and 10K held at Carderock Park along the Chesapeake and Ohio Canal Towpath on November 22, 2026, with a flat, fast trail, walkers welcome, and virtual entry options that include medals and shirts.

Run a scenic Turkey Trot through the historic trails of Manassas National Battlefield. Choose between a 5k or 10k trail course and finish with a glass of wine from the Winery at Bull Run. Your participation supports the preservation of the..

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

A roughly 10 mile trail and canal run near Great Falls on November 26, 2026. Entry opens November 12 and is limited to 29 runners, and participants are responsible for their own medical care.

Join the 28th annual Reindeer Stampede 5k at Killens Pond State Park for a run or competitive walk. This established event supports local cross country and features festive awards and a post race party with seasonal treats.

A looped trail ultramarathon at Prince William Forest Park with 50K, 100K and 100 mile options, staffed and unmanned aid stations, set time limits, a 300 runner cap, and a multi year loyalty challenge.

Trail runs at Fountainhead Regional Park on hiking trails and old dirt roads with 4.8- and 10.5-mile options, aid stations, post-race food, and a kids race and program for ages 2-11.

A holiday-time 50 km out-and-back on the Bull Run-Occoquan Trail from Hemlock Overlook with four aid stations, a downloadable GPX file, and a $20 entry that includes lodge access and an after-event meal. Participants should carry a reusable..

A 50 km New Year trail run at Prince William Forest Park with three repeats of a roughly 10-mile loop, mostly on groomed trails. The event uses an unmanned aid spread at the start/finish and has limited entry.

Experience the rolling hills of Fair Hill Natural Resource Management Area during this winter trail event. Choose between 25K or 50K distances on beautiful single track trails with heated facilities and fully stocked aid stations.

Experience a scenic out and back half marathon on the flat and smooth Dahlgren Railroad Heritage Trail. Enjoy a unique post race campfire with roasted donuts and earn a custom finisher medal.

Support therapeutic riding programs while running through the beautiful forested trails of the Wicomico Demonstration Forest in this inaugural 5k trail race.

A 50 km trail run at Hashawha Environmental Center near Westminster MD featuring 31 miles of mixed surfaces, 5,800 feet of elevation gain, five aid stations and a 9 hour time limit. Lottery entry opens Jan 1, 2027 for ten days.