An annual spectacle in 30 cities around the country, Cupid’s Undie Run is one of the most cheeky (pun perhaps intended) and fun events on the road race calendar. A fundraiser to combat neurofibromatosis, a genetic disorder that causes tumors to grow on nerves throughout the body, the Boston edition takes place February 18 from noon–4 p.m. The festivities kick off at Game On! in Fenway Park, where a pre-run party takes place involving adult beverages and dancing, followed by the main event, a mile-or-so run where participants strip down to their skivvies and sprint through the neighborhood’s streets. Following the Valentine’s Day-themed jog, more dancing and, no doubt, drinking ensues, which the runners will certainly need to warm up after braving the Hub’s cold winter weather in minimal dress. Since its inception in 2010, the organization has raised more than $20 million and involved well over 100,000 brave running enthusiasts, so sign up or sponsor a runner today to make your contribution to this heart-warming charity.