Annapolis Pride
The Annapolis Pride Parade celebrates the LGBTQ+ community, engaging residents, businesses, and groups to unite in welcoming and embracing diversity in Annapolis.
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Commissioning Week
Commissioning Week, which occurs every May, involves a whole week of celebratory events and culminates with the graduation of the United States Naval Academy Midshipmen.
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Annapolis Pride
The Annapolis Pride Parade celebrates the LGBTQ+ community, engaging residents, businesses, and groups to unite in welcoming and embracing diversity in Annapolis.
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Annapolis & Anne Arundel County Arts Month
Anne Arundel County Arts Month is an annual celebration of Annapolis and Anne Arundel County’s talented and diverse local arts community. Explore galleries, take in a performance, or see art in action with the plein air festival from...
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Let's Go! Music Festival
Let’s Go! Music Festival was created by local music lovers. After attending multiple music festivals nationwide, they wanted to bring that experience to their hometown of Annapolis, MD. At the Anne Arundel County Fairgrounds,...
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Annapolis Juneteenth Parade & Festival
Join us in Annapolis for the annual Juneteenth Parade & Festival as we commemorate and celebrate the emancipation of the last enslaved Africans in the United States.
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Paint Annapolis Plein Air Festival
Paint Annapolis is a week-long, juried, plein-air painting competition held each year that brings artists to Annapolis from around the world.
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Santa Maria Cup
The Santa Maria Cup is a premier women’s match racing regatta returning to Annapolis from June 4–7, 2025. Hosted by the Eastport Yacht Club, this event brings elite female sailors from around the world to compete in J/22 yachts on...
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4th of July Parade
Annapolis fireworks are an annual tradition along the shores of historic downtown, watch them from the harbor after the July 4th parade and experience the magic of the holiday in Maryland's capital!
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Dinner Under The Stars
When the sun sets and the string lights flicker on, the historic West Street transforms into a dreamy midweek hangout. Dinner Under the Stars is back from May through September, bringing friends and families together every Wednesday night for...
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Wednesday Night Sailboat Races
Every Wednesday night from April to August (except July 2), Schooner Woodwind and Woodwind II face off in a friendly match race during the Annapolis Yacht Club’s weekly series, offering guests a front-row seat to all the action. While the...
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Naptown National Challenge
HoganLax offers a unique experience with their invite-only tournament, Naptown National Challenge. Teams from across the country and Canada converge in Annapolis & Anne Arundel County for this exciting week-long event.
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Annapolis Crab Feast
Known as the world's largest crab feast, enjoy an all-you-can-eat feast with crabs, delicious sides, drinks, and a bake sale—all while supporting local nonprofits. Join us at Navy-Marine Corps Memorial Stadium for an unforgettable...
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Renaissance Festival
One of Maryland's most anticipated events of the summer, Anne Arundel county plays host to the Renaissance Festival every year beginning the last weekend in August and lasting through October.
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USNA Football
Anyone who’s been to Annapolis during the fall knows about the spirited atmosphere that engulfs the city during football season. Every Naval Academy home game, the city swells to capacity with fans from all around flooding into the...
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