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 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

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.

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 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...

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...

A group of spectators watch a band of musicians on a stage at a festival

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...

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 12, 2023, registration is NOW open.

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.

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, and in 2023, it was rated a top Holiday Parade by USA Today!

Images of runners running in previous run

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.

an aerial view of Navy-Marine Corps Memorial Stadium

Amos 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.

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. This year the event will be held on December 27, 2023!

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.

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!

May Day Display outside Harvest Wood Grill + Tap in Annapolis, MD. Photo from Sue Steinbrook

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...

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.

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,...

Plein Air artist painting State House dome

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.

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...

Plein Air Painter David Diaz

Annapolis Arts Day

Annapolis Arts Week is an annual celebration of Annapolis and Anne Arundel County’s talented and diverse local arts community.

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.

a group of 4 cyclists crosses the Annapolis, MD finish line of the Race Across America

Race 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.

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.

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.