The month of May is arguably the best time to be in Annapolis, whether you’re a Naptown local or just stopping in the city for a brief visit. All of the festivities and fun kick off on May Day — see below — which serves as a little preview of what’s to come: Business owners open up their doors and let in the fresh air, while bright and beautiful flower baskets line decorate their shop’s exteriors to symbolize the arrival of spring.

April showers brought May flowers, and with all of the boating, art, dining and generally celebratory springtime celebrations happening this month, we can finally explore every nook and cranny of our wonderful city without having to wear rain boots or a well-insulated coat. 

This is just a sample of the headline events and seasonal festivities that make their way back to Annapolis this spring. See our events directory for an even more comprehensive list of things-to-do. 

may day in annapolis

Ring in the spring on May Day.

May Day

On Wednesday the calendar finally switches to May, which means the return of the annual May Day Basket Competition in Downtown Annapolis. Now in its 63rd year, the May Day Basket Competition sees residents and businesses in the Historical District and Murray Hill decorate their doorways with baskets filled with fresh flowers to celebrate the arrival of the spring season. The Garden Club of Old Annapolis Towne will spend the day perusing the baskets and selecting the most creative as the winners. If you’re strolling the streets downtown, be sure to have your camera handy to capture the memory of May Day 2019 for years to come.

Boating season finally launches

The beginning of May marks the tail end of the first annual Boat Maryland Week, a new 10-day celebration that highlights the start of Maryland’s boating season and celebrates the state’s deeply-rooted ties to maritime history. Boat Maryland Week features events, festivals, and the latest in boating equipment and maritime art, all to celebrate the opening of boating season, the maritime heritage of our great state, and the historic waters of the Chesapeake Bay.

First Sunday wares.

Don’t be sad when Boat Maryland Week is over; Wednesday Night Sailboat Races are back for the season starting May 1! Each and every Wednesday from May til mid-September, the “Sailing Capital of the World” earns its reputation as up to 150 crews compete in mid-week races around the Bay and Spa Creek to see who can get back to the Annapolis Yacht Club first. Spectators, many of which consider the Wednesday Night Sailboat Races the unofficial start to the weekend, line the docks to take in the festivities with their friends. If you’re in Annapolis this, or any Wednesday, you do not want to miss the experience that is the sailboat races. 

First Sunday festivals return

Yet another super fun and seasonal event makes its annual comeback this May: The First Sunday Arts Festival runs from May to November and kicks off for the season on Sunday, May 5. The arts fest brings over 130 vendors to the first block of West and Calvert Streets, who sell every kind of handmade knickknack and unique piece of art found under the sun — so whether you’re looking for something creative to decorate your home or a one-of-a-kind gift for a loved one, you’ll find it in downtown Annapolis on the first Sunday of the month. Vendors are out selling from 11 a.m. to 5 p.m., and admission is free. 

USNA Commissioning Week

Commissioning Week activities in Annapolis begin on May 17 and run until the 24th, all to honor the First Class Midshipmen upon completion of their four years at Naval Academy. Planned activities include the Color Parade, special awards ceremonies and musical performances, all of which can be found in detail in the Class of 2019’s Schedule of Events

One of the most notable features of every annual Commissioning Week is the return of the Blue Angels, who fly high over Annapolis during practices and performances throughout the week, and the final graduation ceremony fly-over. Spectators can enjoy the flight squadron’s rehearsal on Tuesday and their official performances through the rest of the week. 

Annapolis Memorial Day Parade

Annapolis’ annual Memorial Day Parade will be held on the holiday, May 27, at 10 a.m. The parade, which consists of marching bands and veteran, community and patriotic organizations, follows the traditional route beginning on West Street at Amos Garrett Blvd., before it makes its way around Church Circle and down Main Street, then ends at City Dock. Immediately following the parade is the annual wreath-laying ceremony at Susan Campbell Park. Both the parade and the ceremony are open to the public; all are welcome to take part in the festive event that honors and remembers those who have died serving our country.

As the month ends, Dinner Under the Stars begins

There’s no better way to appreciate our beautiful city in the late springtime than by dining under the stars, and on May 29, the weekly spring and summertime event kicks off. Every Wednesday night, the restauranteurs of Inner West Street bring diners their finest offerings under the open skies for a unique al fresco dining experience that’s second to none on warm summer evenings. Live music and dancing, fun art activities and delectable dishes commence under a picturesque starry night.