Annapolis, Maryland, is a wonderful place to spend a holiday or weekend. But it’s even more exciting all-year round. Annapolis has a slew of amazing events and festivals that you simply won’t want to miss. Check out our list of some of the best events happening all-year round in Annapolis.
Local Events and Festivals in Annapolis, Maryland
Black History 365
Black History Month is just around the corner and we here in Annapolis like to commemorate it all-year round with tons of events, festivals, and other opportunities to highlight and celebrate African-American voices and experiences.
Join us for 365 days of Black history, from our annual Juneteenth Celebration in June, the annual Kunta Kinte Festival, and other initiatives spearheaded by the Banneker-Douglass Museum.
Annapolis Restaurant Week
Foodies, rejoice! Annapolis Restaurant Week — running from February 24 through March 3, 2024 — is the perfect week to experience all the best food and drink in Annapolis. Get a taste of everything that Annapolis has to offer, with over 40 local restaurants participating every year and plenty of different cuisines to choose from, whether you’re craving a bit of seafood or something sweet to tickle the tastebuds.
Restaurant Week offers exclusive dining-in and carry-out deals and gift cards from participating restaurants in one of the most picturesque dining destinations in the country. It’s just the right excuse to go all out and try food and places you’ve never tried before.
St. Patrick’s Parade
Annapolis is simply brimming with traditional Irish pubs and bars and this year’s St. Patrick’s celebration promises to be one of the best one yet. Starting on March 17, 2024, this three-day event kicks off with an Irish Hooley (or party) and going on with Shamrock the Dock and an epic parade.
Dress in your best green and prepare for three days of fun festivities, music, dancing, and of course, drinks!
Maryland Day
Celebrate the founding of the state of Maryland with Maryland Day, a 3-day weekend commemorating the birth of this great state. Kicking off on March 22, 2024 and lasting till March 24, 2024, this is the perfect opportunity to learn more about the history of Maryland while you join in on the festivities.
Many tours and historical landmarks offer free admission or huge discounts during the whole weekend, including the Banneker-Douglass Museum, Annapolis Maritime Museum, the Maryland Hall for the Creative Arts, and Historic Londontown and Gardens. There’s never been a better time to take advantage of the season and immerse yourself in the rich history and culture of Maryland.
May Day in Annapolis
Taking a stroll down downtown Annapolis during May Day on May 1, 2024, is like walking through a flower shop. On this day, houses and businesses in the downtown historic district of Annapolis put out arrangements and containers of fresh flowers to celebrate the coming of spring.
An annual tradition of the city since 1956, downtown Annapolis all but transforms into a colorful floral paradise. Why not stop and smell the flowers for a while?
Annapolis Pride
As June rolls around the corner, any LGBT community member or ally knows it’s pride month. Annapolis Pride could easily be one of the most anticipated events of the year, and it’s not hard to see why. Starting off with a parade on June 3 and lasting till the evening with a festival, this celebration of diversity and liberty promises to be as extravagant as it is colorful.
Whether you’re part of the community or an ally, Annapolis Pride welcomes everyone from all different walks of life.
Annapolis Songwriters Festival
Discover the best of local talent and music with the Annapolis Songwriters Festival from September 14 to 17, 2024. Held in venues all throughout downtown Annapolis, including the City Dock stage, the Annapolis Songwriters Festival is modeled after the Key West Songwriters Festival and aims to shed the spotlight on up and coming songwriters and artists from all over the country while showcasing special guests and bands.
This year’s headliners include Blondie, LeAnn Rimes, Patty Griffin, and Marty Stuart, along with several other artists. This is an event you surely don’t want to miss!
Annapolis Crab Feast
When in Maryland, you simply can’t leave without trying some famous Maryland crabs. And where else to enjoy a heaping pile of some of the best crabs in the state than in the Annapolis Crab Feast, the largest event of its kind in the world?
Happening on August 2, 2024, the annual Annapolis Crab Feast is exactly what it sounds like — an all-you-can-eat buffet of Maryland blue crabs, drinks, crab dishes, and other fare, from hot dogs to watermelon. A spectacular feast awaits you!
Maryland Seafood Festival
Still can’t get enough of the local seafood? The Maryland Seafood Festival is one of the longest running traditions in Annapolis. Held since 1966, this year’s Seafood Festival takes place on September 14 to 15, 2024, and brings freshly caught and prepared seafood (incuding fish, crabs, oysters, and shrimp,) local chefs and restaurants, live music, games, competitions, and plenty of activities to keep the whole family entertained.
Have your fill and more at the Maryland Seafood Festival, an absolute must-visit in Annapolis.
Annapolis Boat Shows
The world’s largest in-water boat show is back for another year! Annapolis is, after all, the sailing capital of the world. Where better to have one of the biggest, most prestigious boat shows in the globe? This is your chance to see boats of all kinds, from luxurious yachts to fishing boats, and marvel at the new technology and innovations of the sailing world.
Catch the Annapolis Powerboat Show from October 3 to 6, 2024, and the Annapolis Sailboat Show on October 10 to 14, 2024.
Eastport Yacht Club Lights Parade
Kickstart the holiday season with the Eastport Yacht Club Lights Parade, regarded as one of the best holiday parades in USA Today. Watch stunning, lit-up yachts and vessels sail by from the comforts of your own boat or from any downtown Annapolis street by the water. We recommend watching from any spot in Annapolis Harbor and Spa Creek.
Grab a hot beverage and a loved one and come and see one of the best holiday events in the country.
Every day of the year in Annapolis promises to be one amazing adventure. So mark your calendars and start planning the best vacation of your life!
Book a slip with us here at Annapolis Town Dock Marina today and secure your spot for any or all of these fantastic events in 2024.