A list of our favorite local events for the month of May. Event dates may be subject to change.
The Boatyard Opening Day Rockfish Tournament
Big news! After a two-year hiatus, the much anticipate and celebrated Boatyard Opening Day Rockfish Tournament returned live and in-person on May 1st. This fundraising event—the first of Boatyard’s many successful charity events—is a catch-and-release fishing tournament, with a huge after-party on site at the Boatyard Bar & Grill in Eastport featuring live music, great food, libations, and awards. Visit boatyardbarandgrill.com to see the results.
Treasure the Chesapeake
Show your love for the Chesapeake Bay by joining the Chesapeake Bay Trust’s Treasure the Chesapeake. The gala will be on May 5th from 6 to 9 p.m. at the Baltimore Museum of Industry. The night will include networking with community leaders, delicious dinner with oyster hour, open bar, and wine tasting, as well as a silent auction featuring dozens of local businesses. Find more information at cbtrust.org.
Derby Day at Maryland Therapeutic Riding
On May 7th, celebrate the Kentucky Derby with the 13th Annual Derby Day at Maryland Therapeutic Riding in Crownsville. The day will include a live viewing of the Kentucky Derby, bourbon tasting, hat contest, live and silent auctions, dinner, drinks, and, of course, mint juleps! More information can be found at horsesthatheal.org.
Maryland Craft Beer Festival
Join the Brewers Association of Maryland for the 2022 Maryland Craft Beer Festival. The festival is returning to the Carroll Creak Linear Park in Frederick on May 14th from 12 to 5 p.m. Entry to the event includes beer samples from dozens of Maryland breweries including a few that are not even open to the public yet. There will be over 200 unique beers which have all been brewed in Maryland. In addition to beer, there will be live music, a great selection of food, and plenty of craft vendors to enjoy. Purchase tickets and find more information about this rain or shine event at mdcraftbeerfestival.com.
YWCA 100th Annual Soiree
Gather your fabulous 1920s attire and dance the night away at the YWCA Soiree. This year, the Annapolis YWCA will celebrate their 100th anniversary and are inviting you. The Soiree will be May 13th at 6:30 p.m. at The Westin Annapolis Hotel. More information can be found at annapolisywca.org.
Spring Open House and Public Anniversary Party
Chesapeake Arts Center is having their 20th Anniversary Party and Spring Open House on May 14th at the Chesapeake Arts Center in Brooklyn Park. The free event will have open doors for all, with fun and creative activities for the whole family. Watch dance demonstrations, see artists throw pots on a wheel, create hands-on projects in the arts classroom, tour exhibits in the galleries, and so much more. Visit chesapeakearts.org for more information.
New Orchestra of Washington 10th Anniversary Concert
The New Orchestra of Washington’s artistic director Alejandro Hernandez-Valdez is conducting the special 10th Anniversary Concert. This concert will be dedicated to the most urgent issues of the next decade: Nature and the Environment. The performance will be May 26th at 7:30 p.m. at the Kennedy Center in Washington, D.C. Before the concert, there will be a special panel discussion with conductor Alejandro Hernandez-Valdez, narrator and conservationist David Rockefeller, Jr. and composer Joseph Turrin. Find more information at kennedy-center.org.
Annie
Children’s Theatre of Annapolis is performing Annie throughout May. The irrepressible comic strip heroine takes center stage in one of the world’s best-loved musicals. With equal measures of pluck and positivity, little orphan Annie charms everyone’s hearts despite a next-to-nothing start in 1930s New York City. She is determined to find the parents who abandoned her years ago on the doorstep of a New York City Orphanage that is run by the cruel, embittered Miss Hannigan. With the help of the other girls in the Orphanage, Annie escapes to the wondrous world of NYC. In adventure after fun-filled adventure, Annie foils Miss Hannigan’s evil machinations...and even befriends President Franklin Delano Roosevelt! Find more information and buy tickets at childrenstheatreofannapolis.org.
Tee Up For a Child Golf Tournament
Anne Arundel County CASA is having their 21st Annual Tee Up For a Child Golf Tournament on May 2nd at the Crofton Country Club. CASA (Court Appointed Special Advocates) speaks up for children who have been abused or neglected in court, at school, and in the community. CASA volunteers have been trained to protects a child’s safety and this golf tournament raises money to help that happen. Find more information at aacasa.org.
Fest of Spring Caribbean Wine Food & Music Festival
From noon to 8 p.m. on May 14th, visit the Great Frederick Fairgrounds for the Fest of Spring Caribbean Wine Food & Music Festival. The festival is a celebration of various aspects of the Caribbean culture including cuisine, music, and art. There will be live performances of locally and internationally renowned artists such as Richie Stephens, Bryan Art, Lukie D from Lust, and many more entertainers. Find more information and buy tickets at festofspring.org.
Dragons in the Dena Festival
On May 21st, start your day at Kurtz’s Beach in Pasadena for the Annual “Dragon’s in the Dena” Festival to raise funds for a new flagpole at the Rt. 100 Veteran’s Memorial area. The event will be 8 a.m. to 3 p.m. and feature dragon boat races, water sports activities, and more. Teams will compete in Dragon Boats who are led by a drummer, who is beating time to keep the paddlers in unison, and a helmsperson to guide the boat in this team building competition. For more information, email pasadenabusinessassociation1@verizon.net.
LemonFest
Celebrate Spring at the LemonFest at the Bowie Town Center. The annual festival celebrates spring and diverse cultures and what they bring to our community through music and art. Enjoy artwork, crafts, and vendors as well as live entertainment, shopping, food, fun, mocktails, cocktails, and wine tastings. The festival will take place May 7th from 11 a.m. to 5 p.m. Find more information at lemonfest.org.
Derby Day at Talisman Therapeutic Riding
Talisman Therapeutic Riding is having their 10th Anniversary Derby Day Benefit on May 7th in Grasonville. This benefit will raise money to create a holistic wellness environment using the great outdoors and nature’s wildlife. Find more information at talismantherapeuticriding.org.
Chestertown Tea Party Festival
Memorial Day weekend is back and that means so is the Chestertown Tea Party Festival in Downtown Chestertown. The festival will run May 27th through May 29th and marks the anniversary of one of the area’s most legendary historic events, when the citizens of Chestertown—in an act to show resistance to British rule—tossed a ship’s cargo of tea overboard into the Chester River in 1774. The celebration will include a Friday night block party, Saturday morning 5K and 10-mile race, craft beer and local wine samples, craft vendors, a parade and more. Find more information at chestertownteaparty.org.
C3 Tri-County Classic
Chesapeake Cycling Club’s Spring Cycling Event on the Eastern Shore on May 14th at 8 a.m. starting and finishing at Talbot County Community Center in Easton. Proceeds from these 66.2- and 37.3-mile courses go to ALYN Pediatric and Adolescent Rehabilitation Hospital, Moveable Feast, and Operation Second Chance. Find more information at ridec3.org.
Six Pillars Century Blackwater Tour Fundraiser
Six Pillars Century is back for the 15th year. The routes will be the same as last year and show exactly what Dorchester County has to offer. The Bike Tour will be on May 7th along the backroads of picturesque Blackwater Wildlife Refuge and will include three flat routes: 37-, 56-, or 100-miles. To sign up, visit bikesignup.com/race/md/cambridge/sixpillarscentury.
Academy Art Museum Annual Spring Event
May 14th is an exciting evening at Academy Art Museum in Easton. The Annual Spring Event will be filled with delicious food and drinks as well as extraordinary art. Proceeds from the event provide vital funding for the Museum’s exhibitions and educational programming. Find tickets and the most up to date information at academyartmuseum.org.
Maryland Freedom Swim
Join ShoreRivers on May 15th from 7 a.m. to 11 a.m. for the Maryland Free Swim. Learn to navigate the Choptank River in Cambridge between the bridges from the Talbot County side to the Sailwinds Park beach access point on the Dorchester County side. This is a 2-mile trip across the Choptank River, which will be supported by paddle craft, motor craft, and the U.S. Coast Guard. Find more information at shorerivers.org.
Ride for the Feast
This is the 20th year of Moveable Feast’s largest annual fundraising event. The ride will be May 21st and start and end at the Talbot County Community Center in Easton. Moveable Feast raises money to support their mission to serve people who live at the intersection of serious illness and food insecurity by preparing and delivering medically tailored meals and providing nutrition education, all at no cost to the client. Riders will have the option to ride a 101-, 69-, or 42-mile ride along Maryland’s iconic Eastern Shore. Virtual riders are also able to register and set their own goals and challenges. Find more information at rideforthefeast.org.
Oxford Fine Arts Show
Visit the Oxford Community Center May 20th through 22nd for the three-day annual Fine Arts Show. The prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The show is well-known throughout the region and is celebrated as the season’s “kick-off” for art lovers. There will be a preview party on Friday where attendees will have the chance to meet the artists, view the exhibit, and buy art. The exhibit will be open Saturday and Sunday from 10 a.m. to 4 p.m. Find more information at oxfordcc.org.
