Men in period military costumes walking on a dock past Tall Ships in a harbor

Annapolis Aperture for VAAAC

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!

Historic London Town

Maryland Day

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

Boats at Sailboat show in a harbor

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!

Santa Maria Cup 2023

Santa 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.

a parade of Midshipmen in their dress blues walk down a path

Vietnam 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.

A group of men and women throw their hats in the air upon graduation from the Naval Academy.

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.

A person holds a rainbow flag beneath a rainbow balloon arch.

Annapolis Pride

The Annapolis Pride Parade celebrates the LGBTQ+ community, engaging residents, businesses, and groups to unite in welcoming and embracing diversity in Annapolis.

A group of black people in costumes march in the Juneteenth parade in Annapolis, MD.

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.

4th of July Boating Event

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.

A group of people wearing crab hats sitting around a table picking crabs

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.

Renaissance Festival

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.

A black woman sits on the lap of a statue of Alex Haley

Kunta 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.

Sailboat Show at night

United 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...

A Giant pumpkin sits to the right of a doorway to a Visitor Center with a red door.

Great 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...

Navy Football Stadium, Midshipmen line up on the field before a game

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...

Annapolis Jazz & Roots Festival

Annapolis 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...

Runners running across the Chesapeake Bay Bridge

Bay 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.

A black man playing a guitar sings into a microphone

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...

Eastport Yacht Club lights Parade along the Annapolis City Dock

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. Marvel as the boats suddenly appear out of the cold winter night, illuminated with thousands of colored...

Giant US Flag in Stadium

Military Bowl

The Military Bowl, sponsored by Peraton, returns to Annapolis and the Navy-Marine Corps Memorial Stadium every December.

Bruschetta and a cocktail at the Chart House.

Annapolis Restaurant Week

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

A group of people wearing green walking in a St. Patrick's Day Parade

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!

Annapolis Film Festival film preview

Annapolis Film Festival

Over 70 films from 28 countries around the world will be screened at various locations throughout downtown Annapolis.