Annual Events In Annapolis & Anne Arundel County

 

What is Annapolis Known For?

We get that question a lot; thankfully, we have curated some of our most popular events and festivals for you to discover here in the heart of Maryland.

Besides our historic charm and travel-friendly airport code, BWI (Baltimore Washington Thurgood Marshall Airport), there is much to see and do in this beautiful seaside town. Annapolis & Anne Arundel County are ideally situated on the Chesapeake Bay, which makes it perfect for concerts, parades, romantic getaways, family trips, and festivals.

Discover the best of the Chesapeake Bay on your next adventure to Annapolis & Anne Arundel County!

 

Explore Annual Events in Annapolis & Anne Arundel County!

Black History 365

We have curated a list of events, blogs, and organizations dedicated to African American History and Heritage. When planning your visit to Annapolis & Anne Arundel County, begin your journey with one of these institutions. The...

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Annapolis Restaurant Week

Foodies of many different tastes are readying their palates for a week of deals and savory dishes.

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St. Patrick's Parade

If there's one thing Annapolis knows it's Irish Pubs and a good time, and the annual Annapolis St. Patrick's Parade is one of the highlights of the year!

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Annapolis Film Festival

Over 70 films from 28 countries around the world will be screened at various locations throughout downtown Annapolis. This yearly event attracts award-worthy films, with many debuting at the Annapolis Fesival!

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Maryland Day

Chesapeake Crossroads Heritage Area has partnered with regional heritage organizations and businesses to celebrate the founding of Maryland.

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Spring Sailboat Show

Join sailors and cruising enthusiasts this April in America's Sailing Capital, Annapolis, MD for the Spring Sailboat Show and Cruisers University!

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May Day in Annapolis

Anyone who’s been to Annapolis on May Day knows it’s one of our most beautiful days of the year. For decades, passersby have walked the streets of Downtown Annapolis, camera in hand, ready to capture the baskets of beautiful...

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Santa Maria Cup

The Santa Maria Cup is the second stop on the 2024 Women’s World Match Racing Tour. Returning after a 10-year break, the 2024 regatta will be the 23rd running of this event, hosted in Annapolis by the Eastport Yacht Club.

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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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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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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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HoganLax Naptown 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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4 th Of July Weekend

Annapolis fireworks are an annual tradition along the shores of historic downtown, watch them from the harbor after the July 4th parade.

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Annapolis Crab Feast

Known as the world's largest crab feast, the event is an all-you-can-eat/drink party organized by the Rotary Club of Annapolis to raise charitable donations for local community and organizations.

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Annapolis Songwriters Festival

Modeled after the hugely successful Key West Songwriters Festival, the largest festival of its kind in the world, the Annapolis Songwriters Festival serves to bring our love for music to the bay! Like Key West, Annapolis has its own...

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The Maryland Seafood Festival

The Maryland Seafood Festival has been gracing the shores of the Chesapeake Bay since 1966 with delectable crab, oysters, shrimp, mussels, and locally caught fish prepared any way you like it! This iconic festival will be held in the heart of...

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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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Annapolis Boat Shows

With nearly 150,000 attendees from around the world flocking to Annapolis for the world's largest in-water boat shows, there's no better place to catch a glimpse of cutting-edge designs and sleek classics than right here in...

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Kunta Kinte Heritage Festival

New Date! October 28, 2023 for the Kunta Kinte Heritage Festival is a celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent that takes place on the shores of...

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Great Annapolis Pumpkins

Come to Annapolis & Anne Arundel County in search of the Great Pumpkins! You cannot miss these 1,000-pound pumpkins that crop up in early October. Snap your picture with them using the hashtag #GreatAnnapolisPumpkins for a chance to win...

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Bay Bridge Run

Run or walk the Chesapeake Bay Bridge in this iconic 10K race across the Bay! Mark your calendars for November 12, 2023, registration is NOW open.

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Annapolis Chocolate Binge Festival

Discover all things chocolate at the Annapolis Chocolate Binge Festival, from candy & sweets to coffee & hot cocoa, culminating in the grand illumination of West Street.

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Eastport Yacht Club Lights Parade

The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December, and in 2023, it was rated a top Holiday Parade by USA Today!

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Military Bowl

The Military Bowl, sponsored by Peraton, returns to Annapolis and the Navy-Marine Corps Memorial Stadium every December. This year the event will be held on December 27, 2023!

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New Year's Eve in Annapolis & Anne Arundel County

Annapolis is a magical place for creating holiday memories with family and friends. Especially on New Year's Eve!

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Naptown Half Marathon & 10K/5K

This annual event has lots of options, including a 5K, 10K, or Half Marathon, and allows event participants to run through Downtown Annapolis and parts of Anne Arundel County, Maryland. 

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