Experience
Discover Annapolis Waterfront Hotel
Each season leaves its mark on the harbor. In winter, the lights multiply, the air sharpens, and familiar traditions return to the calendar. From races across the Bay to boats lit for the holidays, Annapolis feels both storied and alive. Here’s what’s waiting nearby.
Bay Bridge Run
November 9, 2025
One morning a year, the Chesapeake Bay Bridge belongs to runners. The eastbound span closes to traffic, making way for a 10K course that stretches high above open water, with nothing but sky, steel, and sea in every direction. The views are rare. The finish line, hard-earned. And when the race ends, the celebration begins: live music, food trucks, and waterfront revelry, Annapolis-style.
Midnight Madness
December 4th, 11th, & 18th
On a trio of December evenings, downtown Annapolis comes alive after dark. Stroll brick-lined streets beneath glowing garlands and canopies of snowflakes. Sip something warm, browse locally owned shops, and enjoy free street performances that feel straight out of a storybook. The first two Thursdays run until midnight, with the final night wrapping up at 11 PM—a festive tradition that lights up the whole city.
Annapolis Holiday Market
December 2025 – Dates TBA
Framing the historic waterfront, the Annapolis Holiday Market brings together more than 100 regional artisans and food vendors. From Chesapeake-made crafts to hot cider in mittened hands, it’s a chance to experience the city at its most festive.
Eastport Yacht Club Lights Parade
December 13th
Every December, a fleet of boats trimmed in lights sails across the Annapolis Harbor, a decades-old tradition known as the Eastport Yacht Club Lights Parade. It's Annapolis at its most magical, blending maritime pride with holiday spirit. Watch from the Spa Creek Bridge, catch glimpses from a pocket park, or enjoy the view with a warm drink from our dockside perch
Candlelight Concerts
This December, experience the magic of live music under the glow of candlelight at Annapolis Waterfront Hotel.
December 14, 6:30 PM – Candlelight: Coldplay & Imagine Dragons — A stunning tribute featuring the biggest hits from two iconic bands, reimagined by a string quartet.
December 21, 6:30 PM & 8:30 PM – Candlelight: Christmas Carols on Strings — Celebrate the season with timeless holiday favorites performed in a warm, candlelit setting.
Tickets from $51.
Military Bowl
December 27th
College football finds a home in Annapolis each winter, as teams from the ACC and AAC face off at the Navy–Marine Corps Memorial Stadium. The Military Bowl turns the city into a stage for parades, pageantry, and pride, all in support of veterans and their families. Kickoff may be at 11 AM, but the energy lasts all day.