May Day - A Beautiful Day in Annapolis

May Day is one of the most beautiful days in Annapolis. On May 1st the doors of homes and businesses in our centuries-old City of Annapolis are adorned with baskets full of fresh-cut flowers and colorful ribbons. If you haven't yet treated yourself to a stroll along the streets of Annapolis' Historic District on this day of days, this is the year to indulge.


What began as a Garden Club of Old Annapolis Towne beautification project in 1956 has grown into a tradition in which residents and business owners compete for winning ribbons and an invitation to the Garden Club's Annual Tea. 


If you start your day early, you'll catch the flowers at their best. To be considered in the judging, all baskets must be hung by 10:00 a.m. as that is when the 25-strong Garden Club membership takes to the streets of the Historic District and Murray Hill to begin the annual judging. With an over 65-year track record, they have it down to a system. If you keep your eyes peeled, you might just catch them in action. They'll be carrying baskets of flowers decorated with streamers as they walk around awarding blue, pink, yellow, and purple ribbons.


Ribbons are pinned to winning baskets in several categories. All of the lucky winners will be invited to an old-time tea at the home of a Garden Club member. The special occasion makes all of the hours that go into creating a stunning floral display well worth it. Winners who attend the tea will feast on traditional tea sandwiches, cookies, and petit fours, some made from the same recipes of over sixty years ago.

Don't miss this once a year, rain or shine event, to see Annapolis in all of its spring glory. Regardless of whether they capture a ribbon, all of the baskets are winners, and if you take the time to walk our streets and take in the beauty of May Day in the City of Flowers by the Bay, you'll be the lucky grand prize winner!

How to Enter (Adjustments for 2020, there will not be any judging this year)


Baskets to be judged will be those in the downtown area who receive a May Day flyer on their doorstep.

ALL baskets must be visible from the street by 10:00 am on May Day.  Judging takes place between 10 am and Noon. 

Residential arrangements of fresh-cut flowers must be in baskets.

Business arrangements of fresh-cut flowers may use containers related to their business.

All baskets (adult and children) must include a card with the name of the entrant.

Entrants age 12 and under should include their age.  Pink ribbons will be awarded to the 12 and under age group.

Adult ribbon winners are invited to the Garden Club of Old Annapolis Towne's May Tea.  Children are not included.

Routes for Judging May Day Baskets

The History of The Garden Club of Old Annapolis Towne

“The project of this garden club is to develop and preserve the small town gardens in Annapolis.” May 24, 1955


The 1950’s: The Garden Club of Old Annapolis-Towne held its first meeting on May 24, 1955, at the home of Mrs. Jesse Wilkins located at 232 Prince George Street. Under the direction of Mrs. Edith Roberston, the club was formed in an effort to expand the activities of the Federated Garden Clubs of Maryland. Seven ladies from Annapolis decided to create The New Town Garden Club, which immediately changed its name to Old Annapolis-Towne Garden Club.  The charter members were:  Mrs. Philip Briscoe, Mrs. Edward Burgess, Mrs. Ross Collins, Mrs. J. LeVoy Hill, Mrs. William Paca, Mrs. Edith Robertson, and Mrs. Jesse Wilkins.  At their initial meeting, the ladies determined that annual dues would be $1, and set the limit for membership at twenty-five members.  They immediately began to support local civic organizations such as Historic Annapolis, Inc. and the Chase Home.


By early 1956, the membership had grown to nineteen members, the club decided to take on an annual project to benefit the community.  Hence, the annual May Day Baskets event was conceived by Mary Louise Briscoe.  In an effort to beautify Annapolis, the Garden Club asked residents of downtown Annapolis to decorate their front doors with flower arrangements and judges awarded ribbons for the best displays. In addition, the first May Day Tea was held on May 1, 1956, at the home of Mrs. McWilliams on 61 Franklin Street. There were 135 tickets sold for fifty cents each and members of the club served tea from 3 to 5 in the afternoon.  The next year, for the first time, the May Day prizes for best baskets were divided into two categories—private homes and businesses—and ribbons were distributed for 1st, 2nd, 3rd places as well as an honorable mention. 


In January 1957, the club officially changed its name to The Garden Club of Old Annapolis-Towne. The category of honorary membership was established, with the first honorary member being Mrs. Estabrook, followed by Mrs. Philip Briscoe in 1958.  Honorary membership was limited to past active members.


Later that year, the club gave a gift of $10 to Historic Annapolis, Inc. and assumed the care of their garden located at 64 State Circle. According to an account by Mrs. Edith Roberston: “Here were planted daffodils, Virginia bluebells (a lovely contrast), chrysanthemums, hollies, and small boxwood, and an old brick wall, long hidden by weeds and moss, was discovered.” In 1959, the club purchased and planted hemlocks, bulbs, and lilies, as well as bought iron furniture for the garden at Historic Annapolis.  In addition to the work for Historic Annapolis, Inc. and the May Day Baskets, and the club supported the annual Hammond Harwood House Christmas decorations, specifically coordinating the arrangements in a lovely bed-chamber. 


The 1960’s: In 1960, the club decided to relinquish stewardship of the Historic Annapolis garden in lieu of a new project to further beautify the city of Annapolis.  The idea was to provide an incentive to neighborhoods to clean up and further beautify their streets.   The club provided window boxes, filled with flowers, to an entire street in the historic section of Annapolis. The first window boxes were installed at the YWCA on State Circle and on lower Cornhill Street.  Additionally, the club began a decade's long collaboration with other local garden clubs to create and install boxwood wreaths on the State Circle lamp posts during the Christmas season to beautify the city.


For May Day that year, the Garden Club divided the city into four districts for judging purposes.  Each district was awarded ribbons for first, second and third place.  Additionally, ten ribbons, in each district, were given for honorable mention.  Three districts encompassed the business sections of Annapolis:  Maryland Avenue, Main Street, and West Street.  The fourth area covered the entire residential community.   A new category was created for the special buildings throughout the city, and by 1964 a children’s category was established.  Additionally, the club decided to no longer hold the May Day Tea on the same day that the judging took place and in 1967, a new category of membership for the garden club was created: associate member.


The 1970’s: During the 1970’s, the Garden Club channeled its civic work to what was then called Anne Arundel General Hospital (now Anne Arundel Medical Center).  The club agreed to adopt the circle project at the entrance to the hospital.  A landscape architect, William H. Potts, Jr. of Reston, Virginia, created the plan and under the direction of Mrs. Edward Burgess, the circle planting was completed in 1978. The club then agreed to plant an additional garden for the hospital on either side of the new glass corridor passageway, which connected its old and new buildings.  Meanwhile, the club continued to work on the Christmas projects at Hammond Harwood House and the State Circle wreaths.  Making and hanging swag decorations throughout the historic district became another Christmas tradition for The Garden Club of Old Annapolis-Towne.


The 1980’s:  In 1980, the club voted to work on the gardens at Maryland Hall and also installed window boxes there.  By mid-decade, the club began a relationship with Crownsville Hospital by donating plants and funds to the greenhouse and by making wreaths to decorate the hospital at Christmas.  In 1988, in an effort spearheaded by Barbara Tower, the Green Thumb Award was created.  Local businesses and residents were acknowledged for their efforts towards beautification in downtown Annapolis.


The 1990’s: The 1990’s ushered in a new era of bringing nationally known garden lecturers to Annapolis.  The joint efforts of Four Rivers Garden Club and The Garden Club of Old Annapolis-Towne resulted in sponsored lectures by Eleanor Weller and Philip Watson. All the while, the club continued its support of the local civic organizations that had become a tradition.  In 1995, to celebrate the 40th anniversary of the club, in cooperation with the city arborist, the club planted a tree at the foot of Main Street with a commemorative brass plaque.


The Next Century: By 2000, the club’s ongoing civic projects included continued support of the Hammond Harwood House at Christmas, wreaths for Crownsville Hospital as well as State Circle, and a new project: the care and maintenance of a city garden plot at Northwest Street.  In conjunction with the City of Annapolis’ program called Greenscape, the Garden Club members keep this urban garden space looking well tended and attractive. The annual May Day Basket tradition has become a must see event for many locals as well as visitors, with special trips scheduled to coincide with the contest.  More emphasis has been placed on encouraging participation throughout the downtown area and the May Day Tea is now open to ribbon winners as a thank you event.


The fiftieth anniversary of the Garden Club of Old Annapolis-Towne was celebrated in 2005.  In keeping with the goal that was visualized by the founding members of the club, a raised garden plot, adjacent to the Port Warden’s office at Susan Campbell Park, was landscaped by club members.  Honorary member Susan Carter developed the plan for the garden.  A plaque commemorating fifty years of service to the Annapolis community was placed at the site. 

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