Join the May Day celebrations in Annapolis to welcome spring. These events are a beloved tradition in the locality and are full of color, creativity, and community spirit. In Annapolis, May Day is one of the most beautiful and well-known holidays. On May 1, every year, homes and businesses in the city’s Historic District, which is hundreds of years old, are decorated with bright ribbons and baskets of fresh flowers.
Take a walk through downtown Annapolis on May Day. If you have never done it before, this is the year to enjoy the creativity and charm that make this practice so popular. It is an event that really shows off the city’s beauty and sense of community.
- Date: Thursday, May 1, 2026
- Time: All day (self-guided walking tours recommended during daylight hours)
- Venue: Historic District, Downtown Annapolis, Maryland
About May Day in Annapolis
May Day is an adored annual event in Annapolis, Maryland that beautifully marks the start of spring. Every year on May 1, people, shop owners, and businesses decorate their front doors, windows, and entryways with beautiful baskets full of fresh flowers and bright ribbons. Not only do these beautiful displays show how creative the community is, but they also represent the hope and renewal that spring brings.
Locals and tourists travel through historic Annapolis, where each flower arrangement enhances the city’s beautiful architecture. May Day has become one of the most awaited and beautiful Annapolis events over the years, drawing photographers, flower lovers, and tourists from all over the world.
What is May Day?
Every year on May 1, Annapolis celebrates May Day in a very beautiful way that brings the city to life. This long-standing custom decorates Historic District houses and businesses with brilliant baskets of fresh-cut flowers, turning Annapolis into a spring wonderland.
The May Basket Competition is held every year at the event. People carefully create flower arrangements that are put outside of doors, windows, and shops. In 1956, the Garden Club of Old Annapolis Towne started this popular community event.
May Day is more than just a pretty sight; it is also a celebration of community spirit, the start of spring, and social pride. It gives people in Annapolis and visitors a chance to enjoy the beauty of nature and the charm of old Annapolis.
Darim’s flower stand in front of Reynolds Tavern and other nearby flower stands have a wide range of fresh flowers for people who want to make their own flower designs. Everyone in Annapolis loves May Day, whether they are competing or just strolling through the beautifully decorated streets.
History of Annapolis May Day
Seven women came together in 1955 to start the Garden Club of Old Annapolis-Towne. Their goal was to make Annapolis look better. A custom that started in 1956, the club’s May Day Basket event encouraged people and companies to put fresh flowers on their front doors.
The first May Day Tea took place that same year. The club actively worked on civil projects, including preserving Historic Annapolis, maintaining 64 State Circle gardens, and adding houses, businesses, and children’s entries to May Day.
From the 1960s to the 2000s, the club led attempts to make the city look better by setting up flower boxes, wreaths, and swags and planting at Anne Arundel General Hospital, Maryland Hall, and Crownsville Hospital. In 1988, they started the Green Thumb Award.
In the 1990s, they brought national garden speakers to the city, and on their 40th anniversary, they planted a tree to honor the event. They had a garden and sign at Susan Campbell Park in 2005 to mark their 50th anniversary. The club is still committed to making the neighborhood look better, and the May Day Basket is still its most important event.
Top Tips For Enjoying May Day in Annapolis?
Arrive Early
Start your day early to enjoy the floral exhibits while they are still fresh, and the streets are not too busy.
Explore the Historic District on Foot
Allow enough time to walk through downtown Annapolis, especially around Church Circle, State Circle, and Maryland Avenue, where many of the most specific May Baskets are on display.
Bring a Camera
The creative flower designs look beautiful in the shots. You can take pictures of your favorite baskets or yourself against the amusing backgrounds.
Visit Reynolds Tavern
If you want to get ideas for your own spring setup, go to Reynolds Tavern and check out Darim’s well-known flower stand.
Support Local Businesses
A lot of shops and cafés in the area are celebrating with us. Take some time to look around, shop, or eat lunch at one of the tables outside while enjoying the fun atmosphere.
Attend with Family or Friends
Celebrate May Day with your neighbors. Bring your family or friends and plan to spend the whole day there. Take a break for lunch or coffee and see a lot of sights.
Be Respectful of Displays
Carefully made for the competition, do not touch or move the arrangements while you look at them and take pictures.
Check for Special Events
In some years, there are extra events like walking trips or live music. For more information, go to the Garden Club of Old Annapolis Towne’s website or look at the neighborhood event list.
Where To Stay In Annapolis For May Day?
1. Historic Inns of Annapolis
The Maryland Inn, the Governor Calvert House, and the Robert Johnson House are a group of three beautiful inns that offer both classic Victorian charm and modern comforts. Only a few steps away from the waterfront, the Historic District, and important sites like the Maryland State House
2. Annapolis Waterfront Hotel
A modern waterfront home on Compromise Street that has beautiful views and is close to the Harbor, historic streets, and May Day celebrations.
3. Graduate Annapolis
This small hotel is in the middle of the Arts District and has a fun, colorful design. It has an open bar and services that are good for both couples and families.
4. The Westin Annapolis
A high-end choice just outside the Historic District with large, modern rooms that are pet-friendly, an indoor pool, and easy access to city events on a walk.
5. Loews Annapolis Hotel
This full-service hotel is on West Street, close enough to walk to the May Day shows. It has thoughtful services and a modern look.