Annual Events & Festivals
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 the ideal venue for concerts, parades, and festivals.
Our St. Patrick's Parade is one for the ages and draws in the best pipe and drum crews from across the northeast! Or maybe the arts are more your speed? Then the Annapolis Film Festival or Annapolis Arts Week, with its Plein Air painting exhibition, will knock your socks off. Then there is the Maryland Renaissance Festival which is truly a festival for the (dark) ages!
Adventure in Annapolis abounds year-round, so scroll down for some of the most popular events and festivals in the Mid-Atlantic and begin planning your stay in the Chesapeake Bay Region!
Maryland Day
Chesapeake Crossroads Heritage Area has partnered with regional heritage organizations and businesses to celebrate the founding of Maryland.
Explore MoreSpring Sailboat Show
Join sailors and cruising enthusiasts this April in America's Sailing Capital, Annapolis, MD for the Spring Sailboat Show and Cruisers University!
Explore MoreSanta Maria Cup
The Santa Maria Cup is the second stop on the 2023 Women’s World Match Racing Tour. Returning after a 10-year break, the 2023 regatta will be the 22nd running of this event, hosted in Annapolis by the Eastport Yacht Club.
Explore MoreVietnam War Commemoration
With so much military history to be proud of, Annapolis & Anne Arundel County is the perfect destination to host your group during the United States of America Vietnam War Commemoration.
Explore MoreCommissioning 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.
Explore MoreAnnapolis Pride
The Annapolis Pride Parade celebrates the LGBTQ+ community, engaging residents, businesses, and groups to unite in welcoming and embracing diversity in Annapolis.
Explore MoreAnnapolis 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.
Explore More4 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.
Explore MoreAnnapolis 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.
Explore MoreRenaissance 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.
Explore MoreKunta Kinte Heritage Festival
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 Annapolis City Dock.
Explore MoreUnited States Boat Shows
With close to 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 the...
Explore MoreGreat Annapolis Pumpkins
Come to downtown Annapolis in search of the Great Pumpkins! You cannot miss the 1,000-pound pumpkins that crop up in early October. Snap your picture with them using the hashtag #GreatAnnapolisPumpkins for a chance to win prizes from local...
Explore MoreUSNA 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...
Explore MoreAnnapolis Jazz & Roots Festival
The goal of the Annapolis Jazz & Roots Festival is to foster an appreciation for cultural diversity and artistic excellence in a cordial and inviting atmosphere. The festival's inspiring, educational and fun activities will...
Explore MoreBay Bridge Run
Run or walk the Chesapeake Bay Bridge in this iconic 10K race across the Bay! Mark your calendars for November 13, 2022, registration is NOW open.
Explore MoreAnnapolis 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...
Explore MoreEastport 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. Marvel as the boats suddenly appear out of the cold winter night, illuminated with thousands of colored...
Explore MoreMilitary Bowl
The Military Bowl, sponsored by Peraton, returns to Annapolis and the Navy-Marine Corps Memorial Stadium every December.
Explore MoreAnnapolis Restaurant Week
Foodies of many different tastes are readying their palates for a week of deals and savory dishes.
Explore MoreSt. 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!
Explore MoreAnnapolis Film Festival
Over 70 films from 28 countries around the world will be screened at various locations throughout downtown Annapolis.
Explore More