in April, everyone in the Annapolis & the Chesapeake Bay region is eager to get out and enjoy the warming weather. The Spring Sailboat Show - offering free sailboat rides this year! - jumpstart the spring sailing season for novices and veteran sailors alike. If you're planning a visit to Annapolis in April, the festive atmosphere makes for a fun time for players and spectators alike.

Maryland Chicken Wing Festival
Where: Anne Arundel County Fairgrounds. 

ABC Events is excited to bring you the 6th annual Maryland Chicken Wing Festival. Join us and enjoy wings from some of the best establishments around. This is a family friendly event, with lots of activities, music, and good food and drink!

2020 Annapolis Book Festival
Where: The Key School, 534 Hillsmere Drive, Annapolis
Admission: Free

Recognized as one of the premier community events in the region, the free festival celebrates the beauty, power, passion and excitement of the written word. It includes a full day of discussions with prominent authors, a family-friendly comic-con for children and teens, children’s activities, book signings, live music and new and used book sales. The event attracts more than 3,000 attendees annually. Visit for more information.

Maryland Avenue Festival

Maryland Avenue Earth Day Fest
Where: Maryland Avenue and State Circle, Annapolis 
Admission: Free

It's a green twist on a local tradition! This year's Maryland Avenue Spring Festival lands on Earth Day, making for the perfect day to get outdoors and take in the warming weather. Enjoy an old-fashioned street festival with green exhibitors, merchants, and vendors offering art, antiques, jewelry, fashion, home décor, crafts, food and activities for the entire family. Visit for more information.

Annapolis Spring Sailboat Show
Where: City Dock, Annapolis

Set in the charming and historic seaport of Annapolis, the Spring Sailboat Show is the first opportunity of the year for experienced and novice sailors to shop for the latest in equipment, electronics, clothing and boating accessories at the show’s 100+ on-land nautical exhibits and on-site pro surf shops. The fifth annual in-water springtime show will feature Cruisers University (April 26-28) and more than 80 new and previously-owned sailboats of all types and sizes – including catamarans, mono hulls, racing boats, inflatables and day sailors. Visit the Annapolis Boat Shows online for more information.

Boat Maryland Week
When: TBD
Where: Various locations around Maryland

Welcome to Boat Maryland Week! This 10-day celebration highlights the beginning of Maryland's boating season and the state's deeply-rooted ties to maritime history. From April 26 - May 5, visitors can enjoy everything from events and festivals, to the latest in boating equipment to maritime art, celebrate the opening of boating season, the maritime heritage of our great state, and the historic waters of the Chesapeake Bay during the first-ever Boat Maryland Week.

Annual St. John’s / USNA Croquet Match
Where: St. John’s College Campus Front Lawn, 60 College Avenue, Annapolis
Admission: TBD

The “Johnnies” and the “Mids” vie for the coveted Annapolis Cup during this annual rite of spring. The croquet match brings together two starkly different institutions for an event Sports Illustrated says has “no parallel in intercollegiate sports.” Attendees dress “Great Gatsby”-style while enjoying a lavish lawn party that includes serenades by the St. John’s Freshman Chorus and swing music provided by the Naval Academy’s Trident Brass Band. The “Johnnies” play in different “uniforms” each year – ranging from camouflage khakis, to U.S. Naval Academy imitation Crackerjack, to Vikings’ attire, to bare feet. The “Mids” follow the United States Croquet Association dress code. Visit for more information.

USNA vs. St. John's Croquet Match

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Additional April Links

  • Boat Maryland Week

    Boat Maryland Week

    Celebrate the start of boating season in Maryland.

    Learn more
  • Spring Sailboat Show

    Spring Sailboat Show

    Visit the world's largest in-water boat show in America's Sailing Capital, Annapolis, Md.

    Learn more