When summer settles over the Chesapeake, Annapolis comes alive in all the right ways. With sunlit harbor settings, storied traditions, and vibrant festivals, Annapolis summer is a story best lived on foot, by sail, or from a dockside seat just outside your door.

U.S. Naval Academy Commissioning Week

May 14–23, 2025

A long-standing favorite and powerful experience, Commissioning Week honors the graduating class of Midshipmen with a week of pageantry and patriotism that fills the city. Watch as the Class of 2028 tackles the Herndon Monument Climb, then look to the sky for the thrilling Blue Angels rehearsal and flight demonstration. The week concludes with the Class of 2025’s graduation—a moment that unites families, locals, and guests in observance of service and tradition.

Annapolis Pride Parade & Festival 

May 31, 2025

Annapolis Pride is a joyful explosion of love, color, and community. With floats, live music, dancing dragons, and a sea of rainbow spirit stretching from City Dock to Maryland Hall, the festival is a family-friendly celebration of inclusion and identity. Here, Pride feels both personal and shared, woven into the heart of a city that welcomes all.

Anne Arundel County Arts Month

June 2025

June brings a creative energy to the Chesapeake, as artists and audiences gather across the county to honor expression in all its forms. From plein air painting and gallery openings to live performances and hands-on workshops, Arts Month invites you to explore the region through a cultural lens. Whether you’re strolling downtown, following the Vintage Loop, or discovering installations in unexpected places, inspiration is always just around the corner.

Let’s Go! Music Festival

June 6–7, 2025

Turn up the volume and kick off summer at this high-energy, fan-favorite music festival just minutes away in Crownsville. With headlining acts, local eats, and that unbeatable outdoor concert atmosphere, Let’s Go! hits its stride with two days full of music and momentum. After the final encore, ease back into the coastal rhythms with waterside mornings, historic strolls, and sunset cocktails at the edge of the bay. 

Annapolis Juneteenth Parade & Festival

June 19–22, 2025

Join the city in honoring the legacy of freedom during Annapolis’ Juneteenth Celebration, a moving tribute to resistance, empowerment, and cultural pride. This year’s theme, “160 Years – A Legacy of Resistance,” is brought to life through parades, museum dedications, music, and community storytelling. It’s a meaningful commemoration that invites all to reflect and connect.

Annapolis 4TH of July Celebration

July 4, 2025

Ring in Independence Day with all the small-town charm and waterfront wonder Annapolis has to offer. The festivities include a patriotic parade through downtown, live music, and a grand finale of fireworks over the harbor—best viewed from City Dock, a boat deck, or your room here at the hotel. It’s a quintessential Fourth—spirited, scenic, and unmistakably Annapolis.

Rotary Club of Annapolis Crab Feast

August 1, 2025

A Maryland hallmark like no other, the world’s largest crab feast brings together locals and visitors for an all-you-can-eat showcase of Maryland’s signature dish. Held rain or shine since 1946, this zero-waste event features steamed blue crabs, sweet corn, smoky BBQ, and plenty of local flavor—all in support of Annapolis-area nonprofits.

Your Summer, Dockside 

From timeless traditions to waterfront festivals and open-air feasts, summer in Annapolis offers something for every kind of traveler. Whether you’re here for connection, culture, or crabs by the dozen, the Annapolis Waterfront Hotel places you right in the center of the season—steps from the bay, the history, and every can’t-miss event of the season.