A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of June. Event dates may be subject to change.
Bands in the Sand
Enjoy the outdoor party of the year that you won’t want to miss! Each summer 1,600 guests gather on the beach, dance the night away to live music, enjoy a variety of food, and raise a drink to Save the Bay at Bands in the Sand, benefiting the Chesapeake Bay Foundation. Visit Philip Merrill Environmental Center in Annapolis from 5:30 to 10 p.m. on June 8th. Find more information and get tickets at cbf.org.
Photo by Ken Tom
Girlfriends Party
June 12th is the highly-anticipated Paca Girlfriends Party at the picturesque William Paca Garden in historic, Downtown Annapolis. Enjoy a glass of bubbly and indulge in culinary creations prepared by the area’s premier chefs at the social event of the season. Shop the marketplace, meet and greet with local designers, and connect with a network of influential women, all to support Historic Annapolis. Find more information and get your tickets at pacagirlfriends.annapolis.org.
Juneteenth in Annapolis
Celebrate Juneteenth in Annapolis this year with the annual parade and festival taking place on June 22nd. The parade will kick off at noon at the Annapolis City Dock followed by the music festival at 2 p.m. at Bates Athletic Complex on Spa Road. This year’s parade will feature more floats and more bands to celebrate the emancipation of the last enslaved Africans in the United States. Find a full list of entertainment for the festival and more at theannapolisjuneteenth.org.
Bash for Our Besties
The YWCA of Annapolis & Anne Arundel County is hosting Bash for Our Besties on June 6th at the grounds of Charles Carroll House (pictured) in Annapolis overlooking Spa Creek. This is the YWCA’s main fundraising initiative to ensure nobody is ever forced to return to an abusive home. Enjoy live music with the Bachelor Boys, lite fare from Ken’s Creative Kitchen and Main & Market, a Adirondack and firepit lounge, Retro Cocktail Camper, and more. Find more information at annapolisywca.org.
Photos by Tony J. Photography
Best Of Party
What’s Up? Media’s Best Of Party celebrates the very best restaurants, shops, services, entertainment, and businesses of the region all rolled into one fantastic fundraising event on June 11th at Doordan Institute at Luminis Health Anne Arundel Medical Center in Annapolis. At the party, “Best Of” restaurant winners, and only winners, serve samples of their winning dishes and drinks. This is an amazing community event that always sells out, so be sure to secure your tickets while they last at: whatsupmag.ticketspice.com/best-of-party-2024. The winners are selected by our annual reader’s poll and are featured in this month’s issues!
Hospice of the Chesapeake’s Fashion for a Cause
Fashion for a Cause
Hospice of the Chesapeake’s Fashion for a Cause is at a new location, The Fluegel Navy Alumni Center in Annapolis, this year on June 7th. Over a dozen local community models will display new fashions from area stores including some on Main Street and at Annapolis Towne Centre for an evening of runway fashion, food and cocktails for a great cause. This event raises funds to support Hospice of the Chesapeake’s Chesapeake Kids Program. Find more information and get tickets at hospicechesapeake.org/ffac.
Maryland Fleet Week & Flyover
Maryland Fleet Week & Flyover returns to Baltimore County June 12th through 18th. There is an exciting line up of ship tours, festivals, flyovers, and educational activities at the Inner Harbor, Fells Point, North Locust Point, and Martin State Airport. Ships will be arriving on June 12th, which will include United States and international naval ships, U.S. Coast Guard vessels and more. The week’s flyovers will be Saturday and Sunday (15th & 16th) centered around Baltimore’s iconic Inner Harbor. Find a full list of activities at visitmaryland.org.
Taste for Life
The 25th Annual Taste for Life for American Cancer Society will be at The Center Club in Baltimore on June 23rd from 2 to 6 p.m. Taste delicious cuisine and fine wine while raising money to fund cancer research, education, and prevention. Enjoy live entertainment, a silent auction, and more. Reserve a ticket at tasteforlife.org.
Pints 4 Paws
On June 15th, The Annapolis Homebrew Club and SPCA of Anne Arundel County come together for Pints 4 Paws at Navy-Marine Corps Memorial Stadium in Annapolis. The event, which welcomes leashed pets, will have over 50 homebrew samples, local craft beer, a commemorative glass, food trucks, live music, a silent auction, and more to benefit the SPCA. Get tickets at annapolishomebrewclub.com.
Antique & Classic Boat Festival and Coastal Arts Fair
On June 14th through 16th, the Chesapeake Bay Maritime Museum hosts one of the largest classic boat shows in the Mid-Atlantic region when it welcomes the 36th Antique and Classic Boat Festival and Coastal Arts Fair to its waterfront campus in St. Michaels. This Father’s Day Weekend tradition will showcase wooden and fiberglass classics, vintage racers, and other antique boats. The festival is accompanied by a juried Coastal Arts Fair showcasing vendors whose products, services, and art represent boats, the water, and coastal life. Tickets are on sale now at cbmm.org.
Photo by Missy
Casey Cares Rockfish Tournament
Casey Cares Foundation will host its 7th Annual Casey Cares Rockfish Tournament on June 14th. Boats will leave the Bay Bridge Marina at 5 a.m. and fish until 2 p.m. The celebration continues from 5:30 to 9:30 p.m. at The Inn at the Chesapeake Bay Beach Club. Enjoy cocktails, dinner, music, auctions, and more. Companies are encouraged to register their boat for entry. The event will raise much-needed funding for the Casey Cares Foundation, which provides ongoing and uplifting programs for families with critically ill kids. Find more information at caseycares.org.
Tour de Talbot
Support Talbot Thrive with Tour de Talbot, which will start and end at Easton Fire Hall on June 8th. Ride the scenic roads of Talbot County with a 30-, 40-, or 62.5-mile ride through the flat farmland, water views, wooden bridges, and more on the Eastern Shore! Find more information and sign up at tourdetalbot.org.
Chesapeake Bay Motoring Festival
On June 8th and 9th, stop by The Kent Island Yacht Club for the 8th Annual Chesapeake Bay Motoring Festival to celebrate motoring excellence on the Eastern Shore. Go back in time with antique and classic cars enhanced by classic yachts and antique speed boats overlooking the Chesapeake Bay. Find more information and purchase tickets at chesapeakebaymotoringfestival.org.
Paint Stevensville
The Kent Island Federation of Arts hosts the 8th Annual Paint Stevensville in Historic Stevensville on June 1st. Join or watch artists from all over the region draw and paint the marshes, coves, fields, nature trails, boatyards, marinas, restaurants, store fronts, and historic sites from sunrise to nightfall. Find more information at stevensvilleartsandentertainment.org.
Guardian of the Pearl Rockfish Tournament
The Rock Hall Volunteer Fire Company is excited to host The Guardian of the Pearl Rockfish Tournament, a three-day event to help fund RHVFC, a nonprofit, volunteer lifesaving organization. The tournament also promotes heritage, tourism, and fishing for the town. A Captain’s Meeting on June 7th will be at Haven Harbour Marina Resorts and include raffles, a buffet, and drinks. Then two days of fishing will commence on June 8th and 9th. Find more information at rockhallvfc.org.
Chamber Music Festival
The 39th Annual Chesapeake Chamber Music Festival will have six captivating and diverse concerts between June 7th through 15th at the Ebenezer Theater in Easton. Start the festival off with the Opening Extravaganza on June 7th at 7:30 p.m. with acclaimed musicians performing Richard Stauss’ lush Sextet for Strings and more selections. Find more information and get tickets to individual concerts at chesapeakemusic.org.
