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Loews Annapolis Hotel

Annapolis, MD

Annapolis Events

Special Events in Annapolis and the Chesapeake Bay Area

When it comes to special events in the city of Annapolis and the surrounding Chesapeake Bay area, it’s safe to say that each season has something for everyone.

From flower and food festivals to boat shows and shopping excursions, the numerous Annapolis events near ours hotel offer great ways to enjoy the charms of this historic seaport city. And best of all—Loews Annapolis Hotel puts you at the center of it all.

Read below for our recommendations on the Annapolis, Maryland events you can’t miss.

May Day Baskets (Spring)

Each spring, the town blooms with the sweet scent of flowers for the annual May Day Baskets event in Annapolis. Home and business owners proudly display their arrangements of budding flowers on their porches in hopes of winning the annual competition.

The Blue Angels (May)

Witness angels flying across the blue sky. The Naval Academy's Blue Angels are guaranteed to keep you entertained with this event in Annapolis. Choose a grassy area or watch from a waterfront restaurant as the Angels flip, dip and spin at speeds up to 700 MPH. The show takes place every May.

Rotary Club's Annual Crab Feast (August)

Be a part of the biggest summer event in Annapolis. More than 3,000 guests gather annually to feast on the finest steamed crab available along with a variety of other dishes and beverages. All proceeds from the Annapolis event benefit community programs and organizations—enjoy a great feast for a great cause.

Kunta Kinte Heritage Celebration (September)

Join a celebration of African history, culture, arts and cuisine. Learn about the history of Kunta Kinte, dance to the sounds of talented performers, admire the work of artists and craftspeople, and discover cuisine from a variety of cultures at this Annapolis festival.

U.S. Sailboat Show (October)

Get ready to set sail at the oldest and largest in-water sailboat exhibition in the country. More than 50,000 enthusiasts dock in Annapolis to see some of the world's finest boats. Admire the beauty of the boats, browse through the 200 tents filled with an array of boating equipment, accessories and services.

U.S. Powerboat Show (October)

The display of powerboats at the U.S. Powerboat Show proves one thing—speed comes in all shapes and sizes. Join thousands as they visit the oldest and largest powerboat show in the country. Annapolis City Dock and Harbor showcase more than 415 powerboats, while dry land displays 200 more. Learn about the latest equipment, high-tech electronics, accessories and gear to help you get the most out of your favorite pastime. The event in Annapolis takes place only days following the U.S. Sailboat Show.

Maryland Renaissance Festival (Late Summer/Fall)

Go back in time all the way to the 16th Century at the Maryland Renaissance Festival. Listen to the musicians as they entertain the passersby, watch a glass-blowing demonstration, satisfy your thirst with a mug of ale, then get the latest gossip from the fishmonger. Just make sure you leave time to catch the street performers and the joust competitions.

Midnight Madness (December)

Get ready for the madness and excitement of shopping—all night long. During these two December evenings, retailers greet customers until midnight. Shop along Main Street and get something for everyone on your list. Live music, refreshments and dancing in the streets are all part of this Annapolis shopping event.

Eastport Yacht Club Lights Parade (December)

Celebrate the spirit of Christmas in style with the annual Eastport Yacht Club Lights Parade. Bring the whole family to watch boat-owners show off their holiday decorations as they pass through Annapolis Harbor.

For additional information about any of these events, please speak with our concierge. 

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