When December rolls in, Annapolis doesn’t just decorate, we celebrate big. From quirky traditions to glowing waterfront nights, our city knows how to bring holiday cheer with a nautical twist. Here are four holiday events in Annapolis you can’t miss this season.
Santa Speedo Run 🏃🎅
December 13th
The Santa Speedo Run in downtown Annapolis is holiday spirit at its funniest. Locals and dash through the streets in festive costumes, sometimes with more tinsel than fabric, all to collect toys over the tears for less fortunate children. Whether you run or cheer, it’s pure Annapolis holiday energy.
Midnight Madness 🛍️🌙
December 4th, 11th, and 18th
Experience late-night holiday shopping in Annapolis during Midnight Madness. Historic downtown glows with twinkle lights, carolers, pet alpacas, and special deals as shops stay open late. Grab a hot cocoa, browse local boutiques, then end the night with festive bites at nearby restaurants.
Annapolis Gingerbread Houses 🍭🏠
November 22nd - December 19th
The Annapolis Gingerbread House Display turns downtown into a sugary wonderland. Families, bakers, and chefs craft candy creations that delight kids and adults alike. It’s whimsical, free to explore, and makes for magical holiday photos right at the Visitor’s Center on West Street. Don't forget to vote for your favorite Gingerbread house when you visit us!
Annapolis Chocolate Binge Festival 🍫🎶
December 7th
Calling all chocoholics, the Annapolis Chocolate Binge Festival in Annapolis is a sweet dream come true. Sample truffles, fudge, and cocoa creations from local artisans while enjoying live music and the annual Grand Illumination tree lighting at City Dock.
For the most up-to-date information, please visit https://www.santaspeedorunannapolis.com/, https://www.iwsannapolis.com/annapolis-chocolate-binge-festival, https://www.downtownannapolispartnership.org/midnight-madness, https://www.iwsannapolis.com/event-details/great-annapolis-gingerbread-houses.
