2026 Experiences
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.
Grand Illumination
November 29
Annapolis kicks off the holiday season at Market Space with the annual lighting of the city tree. Gather just steps from the harbor for live holiday music, local performances, and an early-evening countdown as thousands of twinkling lights switch on across historic downtown.
Midnight Madness
December 3, 10, & 17
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 4-6 & 11-13
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 12
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.
Military Bowl
December 28
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 2PM, but the energy lasts all day.
New Year’s Eve Fireworks over Spa Creek
December 31
Ring in 2027 with a waterfront fireworks display reflecting off the water of Spa Creek. Scheduled for 9 PM so guests of all ages can celebrate before midnight, the show is visible right along the harbor, making our dockside vantage point one of the best seats in town.