A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of May. Event dates may be subject to change.
20th Annual Boatyard Bar & Grill Spring Fishing Tournament
One of the most popular Chesapeake Bay fishing tournaments heralding the spring trophy season for striped bass takes place May 6th throughout the mid-Bay and on shore! Anglers and captains (about 100 boats in all) will wet their lines in the early morning, vying for the longest striper in this strictly catch-photo-release tournament. Then the fun begins with the shore party at the grounds of the Boatyard in Eastport for the weigh-in and awards ceremony, complete with live music, food, and drinks. All for charity, benefitting Coastal Conservation Assoc. Maryland, Chesapeake Bay Foundation, and Annapolis Police Dept.’s youth programs. For full details, visit boatyardbarandgrill.com.
Blue Angels
One way we know summer is kicking off is when the Blue Angels visit Annapolis for USNA’s Commissioning Week. The Navy’s Blue Angels have the U.S. Naval Academy Air Show on May 24th. Grab your blanket to lay at a local park or run your boat to the Annapolis Harbor to see the Blue Angels perform over the mouth of the Severn River. Find more information about the show and Commissioning Week at visitannapolis.org.
Photo by Joe Heimback
First Sunday Arts Festival
Inner West Street Association hosts the First Sunday Arts Festival on the first Sunday of every month from May through November every year. The first festival this year will be on May 7th from 11 a.m. to 5 p.m. on West Street in downtown historic Annapolis. Maryland’s premier art festival will feature live entertainment, pottery, wood carving, painting, metalwork, watercolor, jewelry, glass, textile, soaps, garden sculptures, and so much more. Check out the website for a full list of vendors and performers at innerweststreetannapolis.com.
Photo by Emily Kritis
Anne Arundel County Food Bank’s Feeding Hope event will be held on May 18th at Homestead Gardens in Davidsonville. Last year’s sold out event raised over $75,000 for our food-insecure neighbors to have access to free, nutritious food. Check out local businesses coming together for our community for the second Feeding Hope Anne Arundel County. Find more information at aafoodbank.org.
Race Day for Hope
The 26th Annual Race for Hope DC community will come together on May 7th for a 5K walk/run to raise awareness and funds to support the needs of brain tumor patients and their families. The race will start at 9 a.m. at Freedom Plaza in Washington, D.C., followed by a kid’s fun run at 10 a.m., and a closing ceremony at 10:30 a.m. Register now at braintumor.org.
Annapolis Irish Festival
ABC Events presents the Annapolis Irish Festival on May 6th from 11 a.m. to 10 p.m. at Anne Arundel County Fairgrounds in Crownsville. The day will include plenty of Irish food and drink, live music, Irish Dancers, Caledonian Pipes and Drums, the Bastard Bearded Irishmen, Gaelic Mishap, Best Leg men in kilts contest, and so much more. For more information and to get tickets, visit abceventsinc.com.
Derby Day at MTR
Watch the Kentucky Derby in good company this year. On May 6th at 5 p.m., Maryland Therapeutic Riding in Crownsville hosts its Derby Day celebration. The 14th Annual Derby Day will include dinner, drinks, live and silent auctions, bourbon tastings, a hat contest, mint juleps, and a live viewing of the Derby! Find more information at horsesthatheal.org.
Chesapeake Art Center’s Chip In for The Arts Golf Tournament
Chesapeake Arts Center’s 10th Annual Golf Tournament will take place at Compass Pointe Golf Course in Pasadena at 9 a.m. on May 17th. This tournament will raise funds for CAC’s arts and education programs. Last year, this event raised nearly $30,000 and brought together 120 golfers. Enter the tournament by visiting chesapeakearts.org.
Bike to Work Week
Each May, Bike to Work Week is celebrated throughout the United States. This year, Bike to Work Week will be May 15th through May 21st. This event promotes public awareness of bicycling and bike safety. So, this week, bike to work, or anywhere else you may be going, like the local events including the Anne Arundel County Bike to Work Day Pit Stop at Susan B Campbell Park at 7 a.m. on May 18th. Find more information at biketoworkmd.com.
GiGi’s Playhouse Gala
GiGi’s Playhouse Spread Your Wings Gala will take place on May 12th at The Annapolis Waterfront Hotel from 7 to 11 p.m. Your ticket includes a seated gourmet dinner, drinks, music and dancing, live and silent auction, wine pull, raffle, and more, all to support GiGi’s Playhouse Annapolis. Get your tickets at gigisplayhouse.org.
Friends for Friends
Bring your friends together for one of the best ladies’ nights of the year. Friends of the Light House’s Friends for Friends will be on May 18th at Annapolis Waterfront Hotel overlooking the Annapolis Harbor. From 6:30 to 10:30 p.m., enjoy live music, full open bar, light fare, raffles, and discover the best in women-focused businesses. All proceeds will benefit The Light House, a homeless prevention support center. Find more information at friendslhs.ejoinme.org.
Chestertown Tea Party
Spend Memorial Day Weekend in Chestertown at the Chestertown Tea Party. When British Parliament closed the port of Boston in May 1774, citizens of Chestertown set ‘Resolves’ forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents came together, marched down High Street, and tossed the cargo of tea on Geddes overboard. The Tea Party will have a parade and reenactment of the events that happened in 1774 and so much more to offer. Find more information at chestertownteaparty.org.
Derby Day at Talisman Therapeutic
Talisman Therapeutic Riding in Grasonville is hosting their annual Talisman Derby Day signature fundraising event on May 6th. The festivities of the day include a traditional mint julep and bourbon tasting, meet and greet the herd and special riders, delicious appetizers, dinner, and dessert, live and silent auctions, and so much more. Find more information at talismantherapeuticriding.org.
St. Michaels Running Fest
One of just two Maryland events recognized in the Top 100 Half Marathons in the USA will kick off at St. Michaels High School on May 20th. The race will take you through downtown St. Michaels, then through waterfront communities and country lanes back toward Fremont Street to the finish line celebration. This is the flattest and fastest half marathon in the mid-Atlantic! Register today at runstm.com.
Photo by Ser Amantio di Nicolao
Maryland House and Garden Pilgrimage Tour
The Maryland House and Garden Pilgrimage tour will be visiting Queen Anne’s County on May 13th from 10 a.m. to 5 p.m. This tour highlights our architectural and cultural history and shares Maryland’s unique and diverse heritage. Proceeds will benefit the restoration of the Tucker House, built in 1797, in Centreville. The tour will begin at Queenstown Town Hall and will hit Queenstown Colonial Court House, Bowlingly (pictured), White Banks, Strothe Farm, Wright’s Chance, The James Croney House, Tucker House and Gardens, The Kennard School, Lansdowne, and The Church Hill Theater. Get tickets at mhgp.org.
CASA Royale
Think Bond, James Bond at CASA of the Mid-Shore’s spring event: CASA Royale. The event will be held 6:30 to 10 p.m. on May 20th at Trident Aircraft Hangar at Easton Airport and will feature casino games, music, themed cuisine, and cocktails (shaken, not stirred), prepared by Gourmet by the Bay. This is CASA’s first in-person fundraiser since 2019 so grab your 007 or Bond Girl attire and get ready for a hand of poker. Get tickets at casamidshore.org.
