Celebrating May Day: The Evolution of a Long Annapolis Tradition

Photo courtesy of Melissa Huston
Photo courtesy of Melissa Huston
Photo courtesy of Melissa Huston
Photo courtesy of Melissa Huston

For 70 years, on May 1, the streets of Annapolis have burst into color as residents and businesses alike take part in the beloved May Day tradition. What began as a simple gesture of placing small flower baskets on doorsteps has evolved into a grand celebration of artistry, community, and springtime
renewal.

May Day in Annapolis is more than just a floral display—it’s a deeply rooted tradition that brings together generations. The event is sponsored by the Garden Club of Old Annapolis Towne and invites residents and businesses to create floral arrangements displayed on doors, fences, and windows throughout the Historic District. While the tradition originated as a way to welcome spring and spread goodwill, it has grown into a full-fledged community event.

“May Day is one of my absolute favorite days of the year,” said Danie Minor, owner of Dandelions Flower Stand. “The creativeness around the city just shines so bright.” Minor has worked with local businesses like Sea Dog Pet Boutique and Even Keel Wellness Spa to craft displays that reflect their unique identities. Each May Day celebration brings a unique creative vision. One year, Minor noted that Even Keel embraced a nautical theme, while St. John’s College incorporated elements celebrating its big croquet win over the U.S. Naval Academy.

Members of the Garden Club judge the displays and award blue ribbons to the most outstanding arrangements. However, the heart of the tradition is the community’s participation. “Creating May Day baskets in Annapolis is a cherished tradition that brings our whole community together,” said Liz Dooner of the Garden Club. “It draws both locals and visitors from near and far, all eager to admire the beautiful, handmade baskets crafted by residents and business owners.”

Many businesses use their floral arrangements as an extension of their brand, incorporating themes that represent their mission. “Selecting flowers is part art and part science,” said Melissa Huston, owner of Studio H Floral Design. “I want flowers that represent the aesthetics of each location, that are available in the right price point, and have the temperament to survive multiple days outside.”

For Huston, May Day took on a deeper significance in 2020 when, amidst the uncertainty of the pandemic, she used her stimulus check to create stunning floral installations at local restaurants. “I wanted to do something big and beautiful to encourage Annapolitans to stop by local restaurants for to-go drinks and carry out,” she recalled. “Something joyful for a time when we were all terrified.”

One of her largest displays, a whiskey barrel overflowing with 400 stems, became an impromptu photo spot that year. Huston watched from her car sobbing as people lined up to take photos with the barrel and get drinks. This year marks the sixth anniversary of her signature “Barrel of Blooms,” a love letter to Annapolis and its resilience.

The tradition continues long after the baskets have been displayed, with an exclusive May Day Tea held to honor the blue ribbon winners. Hosted in the garden of a Garden Club member, the event features recipes passed down through generations and a traditional maypole, keeping history alive.

Annapolis Moms Display

This year, be sure to stop by Federal House Bar & Grille to see the Annapolis Moms basket on display. While you’re there, enjoy a meal at the restaurant. Mention Annapolis Moms, and 10% of your bill will be donated to Friends of Annapolis Moms, which supports families in need.

How to Best Enjoy May Day

Start early. The displays are ready by 10 AM, and the morning light is ideal for taking in the vibrant colors before the day gets busier.
Take a walking tour. Stroll through the Historic District to see the most impressive arrangements on Maryland Avenue, Prince George Street, and Main Street.
Bring your camera. The floral displays make for stunning photos, and many businesses design their arrangements with Instagram-worthy aesthetics in mind.
Shop local. While you’re downtown, stop into the boutiques and galleries that line the streets.
Enjoy a leisurely lunch. Downtown Annapolis is home to fantastic restaurants with outdoor seating, perfect for soaking in the beauty of the day while enjoying a meal.

Whether through simple floral baskets or elaborate, large-scale displays, May Day in Annapolis remains a testament to creativity, community, and the enduring beauty of tradition.