The Best 2019 Spring Events Near Annapolis, Maryland

Posted by Aaron Drummond on Mar 7, 2019 5:00:00 PM

Are you ready for winter to end? Us, too. As the days get longer and warmer, we all want to be out and about. Luckily, there is no shortage of options for spring events near Annapolis this spring. Here are some of the best ways to shake off the winter doldrums and soak up some springtime in Annapolis MD from March to June 2019.



March 2-10: Restaurant Week, various locations, Annapolis. Foodies, rejoice.  For the first week of March, participating restaurants around Annapolis offer special deals and promotions to showcase their culinary prowess. To see who is participating, visit http://www.downtownannapolispartnership.org/restaurant-week.


March 3-4: Annapolis Irish Weekend, various locations downtown Annapolis. Parade at 1 p.m. March 4 on West Street.


March 23: 8th Annual Annapolis Oyster Roast & Sock Burning, noon to 4 p.m., Annapolis Maritime Museum. $25 for general admission, $75 for People’s Choice tasting.


March 21-24: Annapolis Film Festival, various locations, Annapolis (including St. John’s College, Maryland Hall, St. Anne’s Parish Hall). Admission is TBD. Have the chance to view 70-plus films in four days, meet filmmakers and participate in discussions.



April 6: Maryland Chicken Wing Festival, 11 a.m. to 7 p.m., Anne Arundel County Fairgrounds, Crownsville. A family friendly event, the chicken wing festival gives you a chance to sample delicious wings made by local chefs, paired with craft beer and great live music. Proceeds support local charities. Tickets are $12, general admission ($7 for military members and veterans). A $29 season pass is available from ABC Events, which grants access to the Chicken Wing Festival, the Maryland Latin Fiesta, and the Maryland Seafood Festival in September.


April 6: Annapolis Book Festival, The Key School, Annapolis, times TBD. Celebrate books along with the 3,000 other people who attend this annual event. Well-known authors offer insight into their books and their profession, children can participate in different activities, all with live music and book sales to peruse.


April 6 to May 25: Steeplechase Races, various locations.


April 27: 2019 Annapolis Cup Croquet Match, St. John’s College Campus Front Lawn, 60 College Avenue, Annapolis. Join a giant lawn party and watch St. John’s college play the United States Naval Academy in their annual croquet match. Dress up like it’s the 1920s and swing dance, have a picnic, and cheer on your favorite team. Tickets are $20 per adult and are available online. Children 12 and under get in free. Gates open at 11 a.m., and the croquet match starts at 1 p.m.


April 27:  Montpelier Festival of Herbs, Teas and the Arts, 10 am. to 4 p.m., Montpelier Mansion, Laurel. Free.


April 26-28: Annapolis Spring Sailboat Show, City Dock, Annapolis. 10 a.m. to 6 p.m. April 26-27 and 10 a.m. to 5 p.m. April 28. Celebrate the spring sailing kickoff by learning to sail, browsing for a new boat, competing in the regatta or simply taking in the sites. Tickets are $12 per adult, or $19 for a two-day combo. Children 12 and under get in free.

Woman working in flower shop


May 1: May Day basket competition, various locations, Annapolis. For more information, visit http://www.downtownannapolispartnership.org/may-day-baskets.


May 17-25: USNA Commissioning Week, U.S. Naval Academy, Annapolis. The week includes a flight demonstration from the Blue Angels, the Navy’s flight demo squadron. For a full schedule of activities, visit https://www.usna.edu/CommissioningWeek/_files/documents/2019_Commissioning_Week_Tentative_Schedule.pdf.


May 18: Preakness Stakes, Baltimore. See one of horse racing’s most prestigious races, and the central contest of the sport’s coveted Triple Crown.

June 1: Bay Bridge Paddle, Sandy Point State Park, Annapolis. Paddle the Chesapeake Bay and compete for cash and prizes at the annual Bay Bridge Paddle event. Racers can compete in recreational, intermediate or elite categories, according to their abilities. Entry fees range from $55 to $110 depending on what category and how early you enter, and all participants must sign a waiver. There will be clinics the day before, Friday, May 31. The event supports the Foundation for Community Betterment.

Your Guide to Building or Remodeling Your Custom Dream Home

Looking to move to the Annapolis area? See how Tailorcraft builders can give you the Annapolis design-build home of your dreams. Contact us for a free consultation and take a look at our free eBook  "Building or Remodeling your Custom Dream Home". Whatever your springtime plans, we hope you enjoyed our guide to the best spring activities in and around Annapolis MD. 

Topics: kitchen remodel, bathroom remodel, home remodel, design build remodeling, cost, Spring, Events