This​ chilly Main Street tradition aims to spread holiday cheer to local children in need. Since 2006, hundreds of Santas in Speedos have donated over 5,000 toys and books to make kids smile a little brighter during the holidays. Along with unwrapped toys and books, bring your sneakers, Speedo — or swimsuit for the Mrs. Claus—a bag to put your clothes in while running, a copy of your registration and holiday costumes. Check-in 10:30am at O’Brien’s Oyster Bar in Annapolis for libations, toy drop off and registration. Participate in the run or spectate from the side. After the run, return to O’Briens for the after-party (12:45-3:30pm) with music by the Timmie Metz Band featuring Tambo; $25, RSVP: SantaSpeedoRunAnnapolis.com.