A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of May. Event dates may be subject to change.
Let’s Go! Music Fest
Let’s Go! Music Fest is bringing the entertainment to the Anne Arundel County Fairgrounds May 31st through June 2nd. Listen to music from Taking Back Sunday, Dashboard Confessional, Daughtry, The Revivalists, and many more throughout the weekend. In addition to two stages of entertainment, there will be food and craft beverages from the best of Annapolis’ chefs and vendors. This festival is created for music lovers by music lovers with the backyard feel we all love. Get your tickets and find a full list of performers at letsgofest.com.
Photo by Daniel Djukic
Annapolis Blues FC Home Opener
Annapolis Blues soccer team’s season opener is May 15th against the Maryland Bobcats FC (Germantown, Maryland) at their home field, the Navy-Marine Corps Memorial Stadium in Annapolis. This game also is billed as the 2nd Annual Community Shield Charity Match. Proceeds from this game will go toward various local charities in the Annapolis and Anne Arundel County area. The Blues have three away games after their home season opener and then will be back for home games on June 1st, 7th, 16th, 29th, and July 6th. Get your tickets at annapolisblues.com.
Fairy House Festival
Quiet Waters Park and the Friends of Quiet Waters Park Sculpture committee are hosting this year’s Fairy House Festival at the Holly Pavilion within the park on May 4th at 2 p.m. Fairy houses will be on display along the Holly Trail from May 4th through May 31st. These houses are made with materials found in nature and are on display within the woods of Quiet Waters Park in Annapolis for the whole month. Find more information at fqwp.org.
Annapolis Irish Festival
The Annapolis Irish Festival is back at the Anne Arundel County Fairgrounds in Crownsville on May 4th from 11 a.m. to 10 p.m. The family-friendly event will have plenty of entertainment, activities, music, food, and drink. Entertainment will include live bands, Irish dancers, bagpipes, men in kilts contest, red head contest, and all-things Irish. Find more information and buy tickets at abceventsinc.com.
Maryland Fiesta Latina
After a short hiatus, the Maryland Fiesta Latina is back this Spring. On May 5th from 11 a.m. to 7 p.m., visit the Anne Arundel County Fairgrounds in Crownsville for a celebration of Latino heritage and culture. The festival is the perfect time to learn and celebrate with live music, cultural demonstrations, ethnic food, local artisans, and more. Find more information and buy tickets at abceventsinc.com.
Photo by Nina K Photography
Friends for Friends
The Friends of The Light House Shelter’s fabulous ladies’ night out is at the Annapolis Waterfront Hotel on May 16th from 6:30 to 10:30 p.m. Friends for Friends, which overlooks the Annapolis Harbor, will be the perfect place to discover the best in women-focused networking. The night will have live music, open bar, light fare, raffles, and more. All proceeds benefit The Light House a Homeless Prevention Support Center. Find more information and get tickets at friendslhs.ejoinme.org.
Photo courtesy of U.S. Department of Defense
Blue Angels Air Show
Every year, the Blue Angels flight squadron are a part of United States Naval Academy’s Commissioning Week to celebrate Midshipmen, their families, and the town of Annapolis. This year, the Blue Angels will perform on May 21st (arrival and practice) and 22nd (air show). The show will begin at 2 p.m. on both days, so enjoy from your boat, downtown Annapolis, or bring blankets and chairs to parks and greenspace around the Severn River for the best views. Celebrate graduation with the U.S. Naval Academy and find more information about Commissioning Week and the Blue Angels at usna.edu/commissioningweek.
Gigi’s Playhouse Gala
Gigi’s Playhouse is hosting its annual gala fundraiser on May 17th at The Atreeum at Soaring Timbers in Annapolis. The “I Have a Voice” gala will honor and raise money to support programs for children and adults with Down Syndrome. The gala will include a gourmet dinner, drinks, music, dancing, live and silent auction, wine pull, and more. Find more information and get tickets at gigisplayhouse.org.
Annapolis Opera Vocal Competition
Hear the talented rising stars in the classical vocal genre at the 36th Annual Vocal Competition. Annapolis Opera’s competition will be at Maryland Hall in Annapolis on May 5th at 3 p.m. The free event will showcase singers selected by a panel of renowned judges from hundreds of outstanding applications from across the nation. Find more information at annapolisopera.org.
Washington D.C. Boat Show
The Washington D.C. Boat show will hit the National Harbor on May 3rd through 5th. The second annual boat show will be a weekend on the Potomac River to kick off the boating season. There will be a wide variety of vessels from sailboat to powerboat, and new to quality pre-owned, for sale and to order. Tour the boats, grab food and drinks, and listen to live music throughout the weekend. Cutwater Spirits will have a beach party on Saturday with Bobby McKeys mobile dueling piano bar playing as well as a live stream of the Kentucky Derby. Find more information at dcboatshows.com.
Arundel Rivers on the Half Shell
Arundel Rivers Federation is hosting its annual Arundel Rivers on the Half Shell on May 11th from 6 to 9 p.m. at Camp Letts in Edgewater. This is the largest fundraising event of the year, raising money to protect, preserve, and restore the South, West, and Rhode rivers. The fun-filled evening will have camp fare, drinks, oysters, and a silent auction. Get tickets and find more information at arundelrivers.org.
Bourbon & Blossoms
Maryland Therapeutic Riding is trotting into Spring with its signature soiree. Bourbon & Blossoms will be at Maryland Therapeutic Riding in Crownsville on May 4th at 5 p.m. Live music by the Bachelor Boys Band will be performed while attendees enjoy dinner, drinks, live and silent auctions, bourbon tasting, dancing, and watch the Kentucky Derby broadcast. Find more information and get tickets at horsesthatheal.org.
Photo by Nyia Curtis Eye Opening Photography
Feeding Hope
For its third year, the Anne Arundel County Food Bank will host Feeding Hope, a casual spring garden party mixed up with a mini-food and drink festival, on May 22nd, from 6 to 8 p.m. Presented by the Dietrich Family Foundation, the benefit at Davidsonville’s Homestead Gardens brings together more than 200 food bank supporters to raise funds to help our neighbors in need fill their tables with fresh, nutritious food. Guests enjoy small bites and tastes from a variety of local restaurants and food shops, sip on wines, brews, and cocktails, and dance along to live music from Red Betty & The Ruckus. Find more information at aafoodbank.org.
Rhapsody in Red, White and Blue
The Mid-Atlantic Symphony Orchestra will present Maryland’s premier of Peter Boyer’s “Rhapsody in Red, White and Blue” on May 5th at 3 p.m. at the Todd Performing Arts Center at Chesapeake College in Wye Mills. The musical composition, commissioned by and featuring world-acclaimed pianist Jeffrey Biegel, will celebrate the 100th anniversary of George Gershwin’s “Rhapsody in Blue.” Tickets are available at midatlanticsymphonyorchestra.org.
Tri-County Classic
Chesapeake Cycling Club’s Spring Road Cycling Event will begin at Talbot County Community Center in Easton on May 18th. The Tri-County Classic allows you to choose between a 23.2-, 38.6-, 64.9-, or 102.2-mile course all to support the Wounded Warriors project. The Tri-County Classic will have plenty of rest stops, food, and beer to celebrate the day. Find more information at ridec3.org.
Cambridge Classic Powerboat Races 2024
The country’s longest-running powerboat race is held in Dorchester County. On May 18th & 19th the Cambridge Classic Powerboat Regatta (first run in 1911) will race along the Choptank River in Cambridge. This is the opening race for The Hydroplane Racing League for 2024. Watch the Cambridge Classic from the water or from Gerry Boyle Park at Great Marsh. Find more information at cpbra.com.
Chestertown Tea Party
Join the Revolution on May 24th through 26th with entertainment, education, food, and fun for the whole family at the Chestertown Tea Party. 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. This weekend is an annual reenactment and festival around this event along the Chester River. Dress in costume for the parade, take part in a 10-mile run or 5K, enjoy street performances, colonial crafts, food, and more! Find more information at chestertownteaparty.org.
Oxford Fine Arts Show
Enjoy a three-day Fine Arts Show to start the summer art season. The 2024 Oxford Fine Arts Show will be at the Oxford Community Center May 17th through 19th. The juried exhibit draws collectors from local areas as well as Philadelphia, Virginia, and New York City regions. The 40th Fine Arts Show will feature a preview party on Friday night where attendees can meet the artists. Find more information at oxfordcc.org.
Six Pillars Century
For the 17th year, Six Pillars Century is back on May 4th at Gerry Boyle Park at Great Marsh in Cambridge. This race allows cyclists to ride the back roads of the picturesque Blackwater Wildlife Refuge in Dorchester County. There are three options for the race, a 37-, 56- or 100-mile ride through quaint townships along the Chesapeake Bay. Sign up and find more information at bikesignup.com.
