Photo courtesy of U.S. Dept. of Defense
A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of May. Event dates may be subject to change. Also, be sure to check out our 2025 Philanthropic Event Calendar here.
Photo courtesy of Key School
Annapolis Book Festival
Now in its 22nd year, the Annapolis Book Festival brings nationally renowned authors to our town for panel discussions and book signings. On May 3rd, from 10 a.m. to 5 p.m., visit the festival on the campus of Key School in Annapolis. Interactive, multi-generational, and free of charge, the Festival has something for book lovers of all ages. Combining compelling author panels with live entertainment, children’s activities, huge new and used book sales, and food trucks, the Festival attracts more than 3,000 attendees each year. Learn more at keyschool.org/annapolisbookfestival.
Annapolis Irish Festival
The Annapolis Irish Festival is back and better than ever, this year with a two-day festival at Anne Arundel County Fairgrounds in Crownsville on May 2nd (adults-only, 5 p.m. to 9 p.m.) and 3rd (family-friendly, 11 a.m. to 9 p.m.). Friday night, there are two bands to enjoy: Dublin 5 and Carbon Leaf. Come back the next day for more live music, axe throwing, Irish dancers, bagpipes, best red head contest, the Guinness mile, and so much more. Find more information at abceventsinc.com.
Third Annual Fairy House Festival
Starting May 17th and continuing through June 22nd, Quiet Waters Park in Annapolis will have their 3rd Annual Fairy House Festival. Fairy houses will appear along the Holly Pavilion Trail, which is welcome for all to enjoy! On May 17th at 2 p.m., the Opening Fairy House Festival Enchantment will begin, so get your costumes and get ready to celebrate. Find more information at fqwp.org.
Photo courtesy of Songbird Festival
3rd Annual Songbird Festival
The 3rd Annual Songbird Festival will take place rain or shine at Maryland Hall on May 4th from 10 a.m. to 4 p.m. The Songbird Collective is made up of local Annapolis musicians and aim to connect all women by providing a platform for storytelling and artistic expression in a safe, community space. This festival brings together a diverse group of women, women-owned businesses, services, resources, and more. Find more information and register for free tickets at songbirdfestivalwe.com.
Mental Health Gala & Awards Dinner
National Alliance on Mental Illness (NAMI) is hosting the 5th Annual Mental Health Gala & Awards Dinner on May 17th from 6 p.m. to 10 p.m. Be a beacon of hope to families living with mental illness by attending this event at the Crowne Plaza Hotel in Annapolis. The night will have plenty to look forward to, including featured speaker Daniel H. Gillison, Jr., the CEO of NAMI National. For more information, visit namiaac.org.
Photo by Megan Evans Photography
Friends for Friends
Help end the cycle of homelessness by attending Friends for Friends Supporting The Light House event on May 15th, from 6 to 9 p.m. Enjoy a fabulous ladies’ night out at the USNA Fluegel Alumni Center in Annapolis overlooking College Creek. Dance to live music, enjoy a full open bar, light fare, raffles, and discover the best in women-focused businesses all to benefit The Light House a Homeless Prevention Support Center. Find more information and purchase tickets at friendslhs.ejoinme.org.
U.S. Naval Academy Commissioning Week
One of the most eventful weeks in Annapolis comes every May with the U.S. Naval Academy’s Commissioning Week. Celebrate the graduating Midshipmen with activities throughout the whole week in Annapolis. Several of the most exciting events of the week are the Herndon Climb (5/14), the Blue Angels Arrival/Practice (5/20) and Flight Demonstration (5/21), Color Parade (5/22), and Graduation (5/23). Find the week’s full schedule of events at usna.edu/CommissioningWeek/schedule.php.
Photo by Tamlyn Corr Photography
Bourbon & Blossoms Spring Soiree
Maryland Therapeutic Riding’s Bourbon & Blossoms is the perfect Spring Soiree at their campus in Crownsville, to be held on May 10th at 5 p.m. Enjoy dinner, drinks, live and silent auctions, bourbon tasting, dancing, and live music from Mood Swings Big Band to raise money for Maryland Therapeutic Riding. Find more information and get tickets at horsesthatheal.org.
Annapolis Symphony Orchestra/Impact 100 School Concert
Join the Annapolis Symphony Orchestra at Chesapeake Arts Center in Brooklyn Park for an exciting field trip concert that will take students on a rhythmic journey through the world of dance. The shows will be on May 9th at 10 a.m. and 11:30 a.m. This concert will inspire a love for music and performing arts for students aged K-8th grade. Get tickets and find more information at chesapeakearts.org.
Tee Up For a Child
CASA Anne Arundel County’s 24th Annual Tee Up For A Child Golf Tournament will be on May 5th with a shotgun start at 9 a.m. Get on the greens at Crofton Country Club to help raise money for CASA, who believes every child who’s been abused or neglected deserves to have a dedicated advocate speaking up for their best interest in court, at school, and in our community. Find more information and register at aacasa.org.
Bourbon & Blossoms Spring Soiree
Maryland Therapeutic Riding’s Bourbon & Blossoms is the perfect Spring Soiree at their campus in Crownsville, to be held on May 10th at 5 p.m. Enjoy dinner, drinks, live and silent auctions, bourbon tasting, dancing, and live music from Mood Swings Big Band to raise money for Maryland Therapeutic Riding. Find more information and get tickets at horsesthatheal.org.
St. Michaels Running Festival
On May 17th, line up at St. Michaels High School for the start of the St. Micheals Run Fest. The day will offer a half marathon, 10K run, or 5k run or walk. All three races will start at the high school and end on Fremont Street. This half marathon race is one of only two Maryland events recognized in the Top 100 half marathons in the USA, (also helps that it is one of the flattest and fastest 12.1s in the mid-Atlantic). Find more information and get yourself and your friends signed up at runstm.com.
Cambridge Classic Powerboat Regatta
The oldest active powerboat race in the country is back in Dorchester County on May 17th and 18th on the Choptank River. Seventy boats are expected to be on hand to create an exciting two days of racing. This family event will have food and drinks available as well as a kid’s zone and a concert by Tranzfusion. Find more information at cpbra.com.
Tri-County Ice Cream Classic Ride
C3-Chesapeake Cycling Club of the Eastern Shore’s Ice Cream Classic is back and sweeter than ever on May 10th! Beginning at the Talbot Community Center, the annual cycling event will take you on a tour of Talbot, Queen Anne’s, and Caroline Counties, in the heart of Maryland’s Eastern Shore. There are three distances for all abilities of road cyclists—an easier 37-mile ride, a more challenging 65-mile, and a full 100-mile century ride for more experienced cyclists, all on flat safe roads with fantastic rest stops, sag support, and bike assistance. Most importantly, there will be an ice cream pit stop featuring Scottish Highland Creamery. Enjoy a post-race party with tacos, food, and beer. Find more information at ridec3.org.
Sail Selina II 25th Anniversary Celebration: A 1920s Flapper Gala
Celebrate 25 years in 1920s style with a night of dancing, dining, and toasting to the history of the Chesapeake Bay and the Selina II on May 3rd at St. Michaels Harbour Inn. The night will include a DJ spinning the Charleston, gourmet bites and drinks, a photo area, and more to help celebrate the night. Find more information and get tickets at sailselina.com.
Photo by Shane Brill
Chestertown Tea Party
Join the Revolution May 23rd through 25th for entertainment, education, food, and fun for the whole family. In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland, met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then gathered at the town center, marched down High Street to the brigantine Geddes, which was anchored in the Chester River, and tossed her cargo of tea overboard. The annual reenactment of that event is the centerpiece of the Chestertown Tea Party Festival. The re-enactment is scheduled for 2 p.m. All Festival events take place along the Chester River and in the historic district of 18th-century Chestertown. Find more information at chestertownteaparty.org.
