February 13, 2027
New Yorkers aren’t exactly shy about showing off. But running through Manhattan in your underwear in February? That’s commitment.
Cupid’s Undie Run invites hundreds of adventurous souls to strip down for a mile-ish charity run, with plenty of partying before and after. Think skimpy briefs, outrageous costumes, exposed cheeks, and the occasional person who really should have checked the weather forecast.
The fun raises money for the Children’s Tumor Foundation and research into neurofibromatosis (NF), a group of genetic conditions that cause tumors to grow on nerves.
It’s one of the cheekier ways to spend Valentine’s weekend in New York City. And unlike most Manhattan dates, this one actually encourages you to take your pants off.