5K races near Charles Town

The Fall Harvest 5K begins at 9:00 a.m. starting from BB&T Bank. Morning registration and packet pickup are at the Borough Building on Filbert Street. This is a 3.1-mile road race on a flat, fast, wheel-measured course. The plan is straightforward: arrive early, attach your bib, and complete a quick local 5K. Awards are presented to the top three men and women in each age group, with divisions from under 10 to 70+. The fastest overall male and female runners receive trophies. The current course records are 16:56.80 for men and 17:20.65 for women. A $200 prize is offered for the first man and first woman to break the record in the new 70+ age group.

The Tie Dye Run takes place on a fall morning in Hagerstown, Maryland, starting at 17805 Oak Ridge Drive. Participants can choose from three distances: a 5K run/walk, a 10K run/walk, and a Family Fun Walk/Run. This setup accommodates both competitive runners aiming for a personal best and families seeking a shared activity. The family event begins earlier, with the 5K and 10K starting later in the morning after participants have checked in. The event is in its third year and benefits Compassion International, with all proceeds directed to the charity. Awards are presented to the top male and female finishers in the 5K and 10K, as well as to winners in various age groups, from youth categories up to 70 and older. Registration fees vary based on the chosen distance; the 10K is the most expensive, the family event is the least costly, and prices increase after the early registration period closes.

Freedom's Run ties its races to places where Civil War history is part of the ground underfoot: Harpers Ferry, Antietam, and the surrounding region. The series includes a May Harpers Ferry Half & 5K and an October Freedom's Run event, with distances ranging from a full marathon and half marathon to a 10K, 5K, and Kids Fun Run. The Harpers Ferry races run inside Harpers Ferry National Park, while the longer Freedom's Run routes connect runners with historic sites in and around the area. One runner remembered entering Antietam in cold rain, with mist rising from wet earth and the field going quiet as the group ran together. The series also links to Two Rivers Treads, a local running store with a foot-first approach to shoes and gait, and it raises money for a community grant fund supporting local health and community projects.

The Run for MWS 5K is a regional race for Mowat-Wilson Syndrome held in Monocacy Village Park in Frederick, Maryland. The event offers a 5K run/walk and a shorter Fun Run, both starting at 10am, catering to runners, walkers, families, and supporters, not exclusively competitive racers. The course is set within the park, presenting a local, park-based charity race with two distance options. Every registrant receives a Run for MWS: Mid-Atlantic Regional race t-shirt, and participants are entered into prize drawings. Non-runners can participate via a support/spectator option which also includes a shirt.

Boulder Dash uses the roads and packed gravel surrounding Pinesburg Quarry in Williamsport, Maryland, as the quarry itself is closed for race-day safety. The annual event provides three options: a challenging 5 Mile Challenge, a moderate Family Friendly 5K, and an accessible 1 Mile Fun Run. The 1-mile race begins at 9:30 a.m., followed by the 5K and 5-mile races at 10:00 a.m. It accommodates a broad range of participants, from novices and families to those seeking a more strenuous quarry race. The 5 Mile Challenge is the notable course, descending into both the main and old quarry sections, featuring hills, packed gravel, uneven terrain, and some rocky parts. The 5K remains outside the quarry pits on gently rolling roads and gravel, while the 1-mile route is flat and suitable for children or less experienced runners. Registration covers a shirt, custom bib, finisher medal, complimentary photos, and post-race awards. Chip timing and live results are managed by Racine Timing. Awards are presented to the top overall male and female finishers and age-group winners in the 5K and 5-mile races, with 5-mile age groups ranging from 15-and-under up to 80.

The Ghostly Grapes 5k & 10k is a fall trail run and walk held at Two Twisted Posts Winery & Tavern in Purcellville, Virginia. Participants select either a 5K or 10K distance, with both courses utilizing the winery's property and nearby trails by Short Hill Mountain. BISHOP'S EVENTS organizes the run, which accommodates both walkers and runners in a relaxed atmosphere. The start and finish lines are located at the winery on Harpers Ferry Road, leading participants back to post-run food, beer, music, and wine. A complimentary glass of wine is included after the run. The Ghostly Grapes theme incorporates costumes, awards, and race shirts. The event also supports a charity, and early registration provides a reduced fee.

Run the Vineyards - Rocklands Farm 5K is a 5-kilometer race at Rocklands Farm Winery in Poolesville, Maryland, with the start on the winery property. It is a cross-country style run rather than a road 5K, using hard-packed dirt, gravel, and grass trails through vineyard and farm terrain. The race uses chip timing with instant results, and the marked course includes hydration stations and volunteer support. Walkers and children can join, though walkers must register and start behind the runners, and everyone has a one-hour course limit. The event leans into the winery setting after the finish. Participants over 21 get a complimentary drink ticket, with wine tasting and wine sales available on site, plus live music, a food truck, and indoor and outdoor seating. Awards go to the top overall finishers and to age-group winners, three deep for male and female categories, starting with Under 14 and then moving through standard age bands. Registration also includes a custom tech shirt, a souvenir wine glass, free race photos, and free parking, with optional upgrades for long sleeves and finisher medals.

The Bob Gurtler Memorial 5K Run/Walk begins at Grace Episcopal Church in The Plains, Virginia. This small-town 5K is for runners and walkers and honors Bob Gurtler, a former mayor of The Plains, chemical engineer, and lifelong runner. He supported local running clubs and assisted new runners. The route proceeds from the church through town, continues down to Hopewell Road, reaches a halfway point, and returns the same way to finish at the church. The race maintains its community focus, with all proceeds benefiting Peas & Grace, the local food pantry.

The Big Cork Wine Run 5k is a spring 5k held at Big Cork Vineyards in Rohrersville, Maryland. The race begins at 9:00 AM Eastern, with participants assembling at the vineyard on Main Street in Washington County. The setting is the focus: a short road race distance centered at a working winery, distinct from a downtown start or park loop. While specific course maps, elevation profiles, field sizes, or post-race traditions are not provided, the most straightforward description is a 5k morning run hosted at Big Cork Vineyards.

The Berryville Turkey Trot includes a community 5K and a 1 Mile Kids Fun Run at Clarke County Parks & Recreation in Berryville, Virginia. Both races begin and end at the parks and rec building in Chet Hobert Park, a 102-acre park west of town. The 5K starts in the morning, followed by the kids’ mile, which is limited to children age 10 and under. Chip timing is provided by 5 Runners Racing, with SVR support, posted mile markers, and awards for top finishers. The 5K follows a loop course on the park fitness trail and the roadway leading into the park, with a water station on course. The kids’ run is a flat out-and-back on the trail, designed for younger runners rather than a shortened adult race. The event also includes a local food drive and brings a fire truck and ambulance on site for children to explore, giving the morning a family and parks-department atmosphere instead of a race-only setup.

The Thanksgiving Day 5K, Kids' Fun Runs & Tot Trot is a family race morning centered on TQL Stadium, featuring a Chick-fil-A 5K and the Western & Southern 10K, both starting at 9 AM. Younger runners begin the ProAmpac Kids Fun Run, a quarter-mile race, at 8:30 AM from the same start line as the main races. The setup allows adults to select between a short holiday 5K and a longer 10K before the day’s meal, while children have their own quick race and receive medals at the finish. Packet pickup is available with Fleet Feet at TQL Stadium on the Tuesday and Wednesday before Thanksgiving. Free parking is provided in the East Garage, and the post-race party takes place on the field at TQL Stadium with a finish-line celebration sponsored by Pella and other partners.

The Henway Hard Cider Turkey Trot is an annual 5k and 10k race held at Henway Hard Cider in Bluemont, Virginia, located on Foggy Bottom Road. This post-Thanksgiving run takes place at a farm cidery within Great Country Farms, with the Blue Ridge Mountains visible in the distance and surrounded by Northern Virginia Wine Country. Bishop Events organizes the race, with proceeds supporting the local charity Team Virginia. The course winds around the Henway property, presenting a farm-and-cidery focused event rather than a typical city road race. The two available distances accommodate casual runners, walkers, and those seeking a 10k challenge without a significant time commitment. Post-race, participants can remain at the cidery to enjoy a glass of Henway cider with fellow runners, a tradition that defines the event.