Top Annapolis Events in 2025

Annapolis offers a packed calendar of events throughout the year, making it an ideal destination for visitors looking to experience its rich culture and waterfront charm. From festive celebrations to cultural showcases, there’s always something happening just steps from Annapolis Waterfront Hotel. With stylish accommodations, a prime waterfront location, and easy access to the city’s top attractions, our hotel provides the perfect home base for experiencing the best of Annapolis. Here are five of the city’s top events worth marking on your calendar.

Celebrate Irish Pride on St. Patrick’s Day 

Annapolis goes all out for St. Patrick’s Day, turning the historic downtown into a hub of lively festivities. The annual St. Patrick’s Parade on March 9 kicks off at 1:00 p.m., drawing crowds eager to see marching bands, Irish dancers, and festive floats make their way down Main Street. Leading up to the parade, the Shamrock the Dock Festival at Susan Campbell Park offers live music and family-friendly activities. For those looking to start the celebration early, the St. Patrick’s Hooley on March 8 at the U.S. Naval Academy Alumni Center features traditional Irish fare and entertainment.

Browse Local Vendors at the First Sunday Arts Festival 

From May through November, the First Sunday Arts Festival transforms West Street into an open-air market where visitors can discover the work of more than 150 artists and artisans. On the first Sunday of each month, this vibrant festival showcases handmade jewelry, paintings, sculptures, and textiles, along with live music and outdoor dining. Whether you’re searching for a unique souvenir or simply want to soak in the creative atmosphere, this event offers a perfect way to spend a Sunday afternoon.

Watch Fireworks on the 4th of July 

Independence Day in Annapolis is a celebration to remember, with festivities beginning early in the day and culminating in a dazzling fireworks display over Annapolis Harbor. The annual 4th of July Parade winds through downtown, featuring patriotic floats, drum corps, and local organizations. As night falls, the sky lights up with fireworks launched from a barge in the harbor, offering a stunning show visible from multiple waterfront locations. Whether watching from a boat, the City Dock, or the comfort of a hotel balcony, it’s an experience that captures the essence of summer in Annapolis. Stay tuned for event detail updates closer to the time.

Savor Local Dining at the Maryland Seafood Festival 

On August 16, seafood lovers gather at Susan Campbell Park for the Maryland Seafood Festival, a celebration of the region’s rich maritime heritage. The festival showcases the best of Chesapeake Bay cuisine, including freshly shucked oysters, steamed blue crabs, and seafood-inspired dishes from local chefs. In addition to tastings, the event features live music, cooking demonstrations, beer and wine pairings, and a crab soup cook-off. It’s a must-visit for anyone who appreciates fresh, local flavors and waterfront views.

Cozy Up at Holidays on the Harbor 

December in Annapolis brings a festive atmosphere with twinkling lights, holiday markets, and waterfront celebrations. The annual Holidays on the Harbor series features a variety of seasonal events, including the Annapolis Holiday Market at City Dock, where visitors can shop for handcrafted gifts from local artisans. Lights on the Bay, a drive-through light display along the Chesapeake Bay, offers a dazzling way to experience the season. Whether enjoying a holiday cruise, browsing festive markets, or taking in the city’s seasonal charm, December is a magical time to visit.

With a calendar full of events that highlight Annapolis’s culture, history, and scenic beauty, there’s never a bad time to visit. Whether you’re drawn to lively parades, waterfront festivals, or seasonal celebrations, these events offer a glimpse into the city’s vibrant spirit. Annapolis Waterfront Hotel puts you steps away from it all, making it easy to experience the best of the city while enjoying a comfortable and stylish stay.