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 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!
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.
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 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...
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 MoreKunta 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...
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 12, 2023, registration is NOW open.
Explore MoreAnnapolis 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.
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, and in 2023, it was rated a top Holiday Parade by USA Today!
Explore MoreNaptown 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.
Explore MoreAmos Alonzo Stagg Bowl
The NCAA Division, III Football Committee, has chosen Navy-Marine Corps Memorial Stadium in Annapolis, Maryland as the host for the Amos Alonzo Stagg Bowl in December 2022.
Explore MoreMilitary 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!
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 MoreMaryland 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 MoreMay 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...
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 MoreLet'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,...
Explore MorePaint 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.
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 MoreAnnapolis Arts Day
Annapolis Arts Week is an annual celebration of Annapolis and Anne Arundel County’s talented and diverse local arts community.
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 MoreRace Across America - RAAM
RAAM - the World's Toughest Bike Race is among the world's most respected and longest-running ultra-endurance events. Annapolis is delighted to host the finish of this epic 3,000-mile race along our historic city front.
Explore MoreHoganLax 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.
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.
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