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Things to Do in May in Annapolis & Anne Arundel County

Located in the heart of Maryland, Annapolis & Anne Arundel County is the ideal destination for Spring adventures. To simplify planning, Visit Annapolis & Anne Arundel County has compiled a handy list of activities throughout the region. 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.

For more exciting events, festivals, and tours - head to our website,

Signature Events:

May 1 -- May Day in Historic Annapolis (Downtown Annapolis) Every year on the first day of May, 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 amazing 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 in between. Finish off your day with lunch at one of the many cafes or make plans for brunch before the baskets are displayed. You will not want to miss this Annapolis tradition!

May 1 - May 4 -- Santa Maria Cup (Annapolis) This racing regatta is the world's only professional sailing series for women. Join sailors from around the world at this international regatta taking place on the shores of the Chesapeake Bay, May 1- 4, 2023. Annapolis is one of four host cities for this historic event. The Opening Night Ceremony will occur at the Eastport Yacht Club in Annapolis on April 30 (open to the public). Head to the website to learn more about the race times and featured events.

May 13 -- 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 23 & 24 -- 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 2023 performances, several flyovers are accessible at the Naval Academy or along the harbor in downtown Annapolis. 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.

Calendar of Events:

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 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, salsa lessons, and even a Cinco de Mayo-themed cruise from Watermark!

May 5 -- May 6 Annapolis Symphony Orchestra: Saint-Saens Organ Symphony (Annapolis) Grammy-winning violinist James Ehnes is sure to excite with his performance of Erich Wolfgang Korngold Concerto for Violin in D major, op. 35. 8 pm – 10 pm, prices vary, $10 for students.

May 6 -- 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 6 -- Music on the Lawn (Shady Side) Grab your blankets and lawn chairs and join the Captain Avery Museum outside for a day of live music played by local band 600 Pounds of Sin. This event is suitable for all ages; the music starts at 2 pm. $10 Members and Children 13+, $12 Nonmembers, $15 at the door. (Children under 13 are free). Food and beverages will be available for purchase; no outside food & drink except water.

May 6 -- Maryland TacoFest (Annapolis) This inaugural event will highlight 15 participating taquerias on the grounds of Maryland Hall. Attendees will have the option to cast votes for “Best Taco” and “Best Salsa.” In addition to tacos to sample and purchase, there will be drinks, churros, and ice cream. There is no charge to attend. Noon – 4 pm.

May 7 -- 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 - 13 -- Vietnam Veteran War Commemoration (Countywide) In addition to a storied maritime history, Annapolis is home to the United States Naval Academy, Fort George G. Meade (home to all five branches of military service), numerous government agencies, and the National Security Agency or NSA. With so much military history to be proud of, Annapolis & Anne Arundel County is the perfect destination to visit during theUnited States of America Vietnam War Commemoration.

May 14 -- Mother's Day in Anne Arundel County (Countywide) There are so many ways to treat mom to something special and show her how much you care in Anne Arundel County! Celebrate mom 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 13 -- PAINT THE TOWN: An Evening with the Arts (Annapolis) The Arts Council of Anne Arundel County announces the return of PAINT THE TOWN - an evening with the arts to be held at the Westin in Annapolis, Maryland. ACAAC invites the community to join us to celebrate 30 years of supporting the arts in Anne Arundel County! The evening begins with a cocktail reception at 6:30 pm. Tickets are $175 each.

May 13 -- William Paca Garden Plant Sale (Annapolis) A tradition for over 40 years, the William Paca Garden Plant Sale provides the opportunity to take home a piece of history. HA volunteers personally raise over 8,000 plants – perennials, annuals, trees, vines, and vegetables– that represent the best of the old and the new. 10 am – 4 pm, enter through the gate at 1 Martin Street.

May 15 -- June 5 Spring Exhibitions: Elizabeth Myers Mitchell Art Museum (St. John's College) Enjoy the spring exhibition series with St. John’s College at the Elizabeth Myers Mitchell Art Museum. Thought-provoking art displays, artists' talks, and museum tours will be presented throughout the month. Admission is FREE.

May 16 - August 29 -- The Liar (Annapolis) Adapted from Le Menteur (1644) by Pierre Corneille, David Ives’ The Liar is a farcical play filled with fabrications and complications. The story takes place in 1643, Paris, where a charming young man simply cannot tell the truth. Between misunderstandings and intricate lies, this is one of the world’s greatest comedies. Presented weekly on Tuesdays in the outdoor courtyard of Reynolds Tavern. Tickets range from $55 - $75 each.

May 17 -- 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 traditional event. This event usually takes place during Commissioning Week; however, the Herndon Climb will be a culmination of plebe activities going forward.

May 19 -- Jerry Seinfeld Comedy Tour (Arundel Mills) See Jerry Seinfeld on his comedy tour at Live! Casino & Hotel at The HALL at Live! This one-night performance will surely sell out; tickets start at $70+. Doors open at 7:30 pm, and the show begins at 9 pm.

May 19 - 26 -- 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 24 - September 23 -- Dinner Under the Stars (Inner West Street) On Wednesday evenings and select Saturdays through September 23, 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 29 -- 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 the 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!



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