Things to do in May & June in Annapolis & Anne Arundel County

Located in the heart of Maryland along the Chesapeake Bay, Annapolis & Anne Arundel County is the ideal destination for adventure. Boating and sailing season are in full swing; the county is in full bloom, and the United States Naval Academy commissions (a.k.a. graduates) their new class of Midshipmen as Ensigns in the Navy or Second Lieutenants in the Marine Corps. To simplify planning, Visit Annapolis & Anne Arundel County has created a list of seasonal activities so you can enjoy the best the region has to offer! 

May Events

May 1 -- May Day in Historic Annapolis (Downtown Annapolis) Every year, on May 1, historic downtown Annapolis is transformed with colorful arrangements of blossoms and blooms. Containers full of fresh-cut flowers are thoughtfully placed in front of businesses and homes as part of the annual May basket competition. This annual beautification of the city, sponsored by the Garden Club of Old Annapolis Towne, has been an Annapolis tradition since 1956. Stroll the streets and enjoy these inventive and unique creations throughout the historic district. Baskets can be found along Market Street, Conduit Street, Southgate Avenue, Main Street, Fleet Street, Pinkney Street, Cornhill Street, King George, Prince George, Main Street, West Street, and everywhere. Finish your day with lunch at one of the many cafes, or plan brunch before the baskets are displayed. You will not want to miss this Annapolis tradition! 

May – September -- Farmers Markets (Countywide) Spring and summer are the perfect times to set your sights on cleaner eating with a trip to our local Farmers Markets. Source organic vegetables and fruit, dairy, meat and poultry, local pies and jams, honey, and so much more! 

May – August -- TrySail: Two-Hour Introduction to Sailing (Annapolis Neck) This intro to sailing is a great gift or a perfect day on the bay! During your two-hour sailing introduction, you can learn the basics from experienced instructors with hands-on training aboard the reliable Rainbow 24 or relax and enjoy the experience while others do the work. Don't forget to stop for lunch on your way back through town! 

May - August -- Wednesday Night Sailboat Races (Annapolis) Enjoy the magic of the Annapolis Yacht Club's Wednesday Night Sailboat Races in historic downtown Annapolis! Line the harbor to watch the boats roll in or book a sail aboard the Schooner Woodwinds or Wilma Lee for an on-the-water experience. In America's Sailing Capital, you have an entire season to get out and discover the excitement of this Annapolitan tradition. (Every Wednesday, weather permitting). 

May 4 -- Annapolis Irish Festival (Crownsville) Although it may seem like we just finished celebrating St. Patrick's Day, Anne Arundel County hosts an annual festival of all things Irish at the Anne Arundel County Fairgrounds every spring. There will be plenty of Irish music, dancing, singing, food, and drink for the whole family to enjoy. Tickets are $25 in advance and $30 at the door; children under 12 are FREE. Admission includes entrance and free parking to the event. 

May 5 -- Cinco de Mayo in Annapolis & Anne Arundel County (Countywide) discover new ways to celebrate Cinco de Mayo in Anne Arundel County with authentic Latin American cuisine, parties, and salsa lessons! With so many activities throughout the county, you are never far from a celebration. 

May 5 -- Tales of Beatrix Potter (Shady Side) Live performance by the National Ballet Company and School. Join Peter Rabbit, Jemima Puddleduck, and their delightful friends as they come to life with dance and music. More details to follow! Rain Date: May 12. This event is suitable for all ages; the music starts at 2 pm. $12 Members and Children 13+, $15 Nonmembers, $15 at the door. (Children under 13 are free). Food and beverages will be available for purchase; no outside food & drink except water. Please leave your furry friends at home. 

May 5 -- First Sunday Arts Festival (Inner West Street) Every year, from May through November, the Inner West Street Association hosts their monthly arts festival. The streets are closed, and vendors set up their wares in picturesque, charming downtown Annapolis. Shop at the storefronts, listen to music or dine in one of the cafes or restaurants. This event is family-friendly, and friendly leashed pets are welcome. 

May 11 -- Maritime Republic of Eastport .05K Bridge Run (Annapolis to Eastport) Described as "the least challenging athletic event ever conceived" by Runner's World magazine, the .05k extreme sports event is a grueling test of mental and physical toughness. Some competitors have taken up to five minutes to complete the course that begins on the Annapolis side of the Spa Creek Bridge. In a true testament to the difficulty of this race, it begins promptly at the crack o' NOON. Proceeds from race registrations go back into the community. 

May 12 -- Mother's Day in Anne Arundel County (Countywide) There are so many ways to treat the special mother figure in your life to something special and show her how much you care in Anne Arundel County! Celebrate this year with a delicious brunch, lunch, an art show, a brunch cruise, Mother's Day Sail, or a shopping extravaganza at the largest discount shopping destination in the state.  

May 15 -- Herndon Climb (United States Naval Academy) Truly a remarkable sight, the Herndon Monument Climb is the traditional culmination of the plebe year at the Naval Academy. Demonstrating the teamwork and perseverance they have learned during their first year at the academy, the plebes build a human pyramid to remove the "dixie cup" hat at the top of the vegetable-shortening-covered monument and replace it with an upperclassman's cap (a.k.a. cover). After completing the Herndon climb, the first-year students are no longer called plebes but "fourth-class midshipmen." The Trident Brass band will perform at the Zimmerman Bandstand as part of this annual event.  

May 17 - 25 -- Commissioning Week (Annapolis) The United States Naval Academy Commissioning Week is a celebration for Midshipmen, their families, and the entire town of Annapolis. Woven into the fabric of our historic city, visitors come from all over to celebrate this special honor with graduating Midshipmen. Explore hotels, attractions, and more on our website, and plan your stay in Annapolis for one of the year's most exciting events. 

May 18 - September 28 -- Dinner Under the Stars (Inner West Street) On Wednesday evenings and select Saturdays through September 28, the first block of West Street in the heart of downtown Annapolis closes to automobile traffic and welcomes visitors to dine and shop al fresco under a canopy of white lights reminiscent of European open-air cafes. Treat yourself to an evening with family and friends, enjoying live music and art demonstrations against the backdrop of Historic Annapolis. 

May 21 & 22 -- Blue Angels Practice and Performance (Annapolis) Feel earth-shaking, heart-pounding pride every time the Blue Angels take flight over Annapolis skies! For the Blue Angels Commissioning Week 2024 performances, several flyovers are accessible at the Naval Academy or along the harbor in downtown Annapolis. Or book one of the many boat excursions for a waterfront view. Flight schedules are subject to change and weather-dependent, so please check back or follow us on social for updates and changes before your visit. 

May 27 -- Annapolis Memorial Day Parade (Downtown Annapolis) Annapolis holds one of Maryland's largest Memorial Day Parades. It starts at Amos Garrett Boulevard and West St., then goes down West Street to Church Circle and down Main Street to City Dock. After the parade, there is a Memorial Day Ceremony at Susan Campbell Park. Enjoy the parade and stay after for a visit to one of the many ice cream shops in Annapolis! 

May 31 - June 2 -- Let's Go Music Festival (Crownsville) The brainchild of avid music fans and concertgoers, this three-day festival brings top performers and national acts to the Anne Arundel County Fairgrounds every June. This year's lineup of artists includes The Revivalists, The Band CAMINO, COIN, The Moss, HARBOUR, Bush, Daughtry, and more! Get your tickets on the festival website; tickets are available for all three days or per concert.  

June Events

June – January 4, 2025 -- REVISIT/REIMAGINE: The Civil Rights Era in Maryland and Parallels of Today (Downtown Annapolis) From 1964's Bell vs. Maryland to 1963's Treaty of Cambridge, Maryland has been the backdrop to civil rights legislation throughout the years. Additionally, Maryland has been the home to civil rights icons who will forever have a place in the history of this nation, such as Verda Freeman Welcome, Thurgood Marshall, and Gloria Richardson. Explore their stories and more at the Banneker-Douglass-Tubman Museum.  

June 1 -- Annapolis Pride Parade and Festival (Downtown Annapolis) A visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, musicians, motorcycles, and more. Check back for the announcement of this year's Grand Marshal! 

June 1 – 30 -- Anne Arundel Arts Month (Anne Arundel County) This year, the Arts Council of Anne Arundel County has teamed up with AND Creative Studios, Chesapeake Arts Center, and Arts Lab of South County to create a month-long celebration of art called Anne Arundel Arts Month. Find inspiring exhibitions, dance, live music, public art displays, and so much more during this inaugural ode to all things art throughout Annapolis and Anne Arundel County! Read this blog for more inspiration! 

June 16 – Father's Day in Anne Arundel County (Anne Arundel County) Show your pops how much you appreciate all he does with a personal present and the gift of time together. We have a blog of curated experiences for you to discover in Annapolis and Anne Arundel County, as well as some out-of-the-box surprises. Whether you have a golfer, foodie, or boating enthusiast on your hands, we have it all! 

June 21 - 22 -- Annapolis Juneteenth Parade & Festival (Downtown Annapolis) The mission of the Annapolis Juneteenth Celebration is to commemorate the emancipation of the last enslaved Africans in the United States. The weekend features a VIP Gala celebration honoring local activists, a parade, and a festival at the Bates Athletic Complex. The evening culminates in a fireworks display featuring various national and regional entertainment. Free and open to the public! 

Looking Ahead

July 2 – Civil Rights Act Anniversary Commemoration (Anne Arundel County) July 2024 marks the 60th Anniversary of the Civil Rights Act of 1964, a historic law making discrimination based on race, color, religion, sex, and national origin illegal. To honor the people who have stood steadfast in the struggle for change, Visit Annapolis & Anne Arundel County has compiled a list of 60 Civil Rights sites for the 60th anniversary of the Civil Rights Act. Discover the guide on our website and planning tools to explore our rich history and heritage on your next visit to Annapolis. 

July 4 -- City of Annapolis 4th of July Celebration (Downtown Annapolis) Join the city of Annapolis for a patriotic salute to our nation with marching bands, fire engines old and new, cars and vans, service clubs, scouts, and more! ROUTE: The parade kicks off at Amos Garrett and heads down West Street, the wrong way around Church Circle, and down Main Street. Stay for the fireworks over the harbor for a perfect end to your 4th of July weekend! Parade: 6:30 – 8 pm, Fireworks: 9:45 –10:15 pm. (please check www.VisitAnnapolis.org for updates; fireworks are weather dependent) 

Head to our daily events calendar for more exciting events, festivals, and tours.