February 21
Every February in Washington, D.C., Cupid’s season gets literal. It also gets a little cheeky. That’s when runners strip down for the DC Cupid’s Undie Run, one of the city’s most playful winter traditions.
This lighthearted event invites locals and visitors to hit the streets in their underwear. Or whatever makes them feel fabulous. The route winds through Southwest D.C. and delivers a short, spirited dash with big community energy. It’s equal parts fun, fundraiser, and excuse to show off those New Year gym gains.
The DC Cupid’s Undie Run typically kicks off at Union Stage (740 Water St., SW) around noon. From there, participants head out on a roughly one-mile loop around The Wharf. It’s not a marathon. No carb loading required. The focus stays on cheering one another on and spreading good vibes along the route.
Attire runs the gamut. Some show up in boxers or briefs. Others go full theme. Creative costume layers are encouraged. The goal is silliness, not speed. Community matters more than pace.
Organizers run the event as a fundraiser for local health initiatives. Many focus on sexual health awareness and prevention. As a result, the crowd draws hundreds of runners, walkers, couples, friends, and even costumed pups. Rules stay minimal. Outfits must remain public-event appropriate. Enthusiasm is welcome. Indecency is not.
Before and after the run, Union Stage feels more like a block party than a start line. People linger. Photos happen. Filters get used. Music, laughter, and playful embarrassment fill the space.
Whether you run, cheer from the sidelines, or just take it all in, the DC Cupid’s Undie Run stands out as a winter highlight. It’s community, celebration and cardio with a wink. And it’s absolutely worth doing at least once.