The month of May begins with a truly beautiful tradition: May Day. On May 1, the doors of residences and businesses are adorned with baskets bursting with fresh-cut flower arrangements. Visitors roam the town oohing and aahing, and awards are distributed by judges from the Garden Club of Old Annapolis Towne to the decorated doors deemed most attractive. The baskets remain on display the first week of May. Another sight to behold occurs every Wednesday evening in May and throughout the summer season: Wednesday Night Sailboat Races. Whether you're on deck or on the docks watching, a good time is had by all. For many, the most exciting time in May is Naval Academy Commissioning Week, a week-long celebration that includes a grand parade, a fly-over by the Blue Angels and other exciting events, culminating with a graduation ceremony for this year's senior midshipmen.

May Day in AnnapolisAnnual May Day Basket Competition 
When: Friday, May 1st, 2020
Where: Downtown Annapolis

Considered to be one of the most beautiful days in historic downtown Annapolis, May Day greets visitors and area residents with door after door of baskets filled with beautiful spring flowers. Come with camera in hand to capture the handiwork of downtown Annapolis residents and merchants who welcome spring by decorating their doorways with baskets of blooming flowers. Some 20 volunteers from the Garden Club of Old Annapolis Towne judge the entries and invite winners to join them at an annual Garden Club Tea.

First Sunday Arts Festival
When: Sunday, May 3rd (every first Sunday through November 1st) Noon to 5:00 p.m.
Where: First block of West and Calvert Streets, Annapolis
Admission: Free

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street (the Arts District) and Calvert Street next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. Visit for more information.

Live Music at the First Sunday Arts Festival

William Paca Garden Plant Sale
When: May 9th-10th, 2020
Where: William Paca Garden, 1 Martin Street, Annapolis
Admission: Free

Take a piece of the William Paca Garden home with you! Choose from among more than 300 varieties of perennials, annuals, vegetables, herbs, trees and shrubs – including heirloom and “cutting-edge”, native and exotic – that have been raised by Paca Garden volunteers. Gardeners on hand to answer questions. Information-packed catalog available online or for purchase. Free admission includes free tours of the Paca Garden. Proceeds support the William Paca Garden and its programs. Visit for more information.

William Paca House and Gardens

USNA Commissioning Week
When: May 15th -22nd, 2020
Where: U.S. Naval Academy, Annapolis
Contact: 410-293-2292

Each year, approximately 1,000 midshipmen graduate from the U.S. Naval Academy and receive their commissions as officers in the U.S. Navy or Marine Corps. On Monday, cheer on members of the class of 2019 as they attempt to climb the Herndon Monument. Traditionally, the Blue Angels’ flight rehearsal is on Tuesday and the Blue Angels’ flight demonstration is on Wednesday. On Thursday, catch the Color Parade at Worden field. For more information, visit the U.S.N.A. website at

Blue Angels fly by the Naval Academy

Annapolis Greek Festival
When: TBD
Where: SS Constantine & Helen Greek Orthodox Church
Contact: 410-573-2072

The greeks call it Kefi - when the music is playing and the joys of life consume you making you want to jump, dance and yell OPA! The Annapolis Greek Festival is all about Kefi! Greek food, music and dancing. Enjoy the wide selection of authenitc greek food and pastries, especially the freshly made loukoumades. Kids will enjoy a large children's area, filled with moon bounces, games and more. To learn more, visit

Annapolis Memorial Day Parade
When: May 25th, 2020 
Where: Parade kicks off at 10:00 am at Amos Garrett Boulevard and West St., Annapolis

The parade will follow the traditional route with staging at Amos Garrett Blvd. It will process down West Street to Church Circle and down Main Street to City Dock. It will be followed by an annual Memorial Day Ceremony at Susan Campbell Park. It’s an excellent opportunity to pay our respects to the men and women who made the ultimate sacrifice for our country. Visit for more information. 

Dinner Under the Stars
When: Wednesdays, May 27th through September 16th, 2020
Where: 6pm - 10pm, West Street, Annapolis

The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffic on Wednesday evenings and filled with café tables reminiscent of the open air cafés in France, Spain, and Italy. Visitors and area residents are invited to dine, stroll and shop along West Street while enjoying live music beneath a canopy of lights. Visit for more information. 

dinner under the stars

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Additional May Links

  • Commissioning Week

    Commissioning Week

    Commissioning Week involves a full week of celebratory events and culminating with graduation of the United States Naval Academy

    Learn more