2020 Biggest Events in Annapolis, Maryland

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Annapolis, Maryland is an exceptionally vibrant city, bursting with beautiful beaches and a bountiful history, but that’s not all! A boatload of engaging events adds to the Annapolis allure…

Jumpstart the season with the Annual Spring Sailboat Show April 24-26! Then, the doors of homes and businesses are adorned with baskets brimming with fresh flowers in celebration of May Day. May 15-22 is Naval Academy Commissioning Week with a grand parade and a Blue Angels flyby. Partake in cultural foods, music and more at the Annapolis Greek Festival this spring as well. OPA!

Check out The First Sunday Arts Festival which runs May till November and where work from over 100 talented local and regional artists is on display; restaurants set up outdoor cafes; and live entertainment is enjoyed by all. Shop, stroll and dine under a canopy of lights throughout the summer months because these delightful open-air cafes are open every Wednesday from June through mid-September as well. Wednesday just happens to be a very good day of the week because there are also sailboat races every Wednesday night in the summer.

Savor delectable seafood dishes along the scenic Chesapeake Bay at the Annual Maryland Seafood Festival September 7th and 8th. Then attend the Annual Boatyard Bash at the Annapolis Maritime Museum September 14th, where world-class musicians will belt out Buffet and a grilled buffet dinner with cocktails will benefit children’s education.

Soak up some history at the Historic Haunting Tours Fridays and Saturdays if you dare. Then, celebrate the holiday season with the Annapolis by Candlelight Walking Tour November 8th and 9th and a spectacular tree lighting ceremony – timing TBD.

Attention chocolate lovers! You know who you are. The Chocolate Binge Festival is December 2.  Then, beautifully decorated boats light up the harbor at Eastport Yacht Club’s Light Parade the 2nd Saturday in December; and the College Bowl Game will cap off the year December 31st, followed by a festive fireworks display.

Gary Wells

Owner of Window Expressions, Annapolis' premier custom window treatment specialist. With years of of experience in the industry, Gary takes pride in his keen eye for design and his ability to transform clients' visions into reality. He finds joy in leading a local, family-owned business committed to putting the "custom" in customer service.

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