Chesapeake Bay Paddle
Mark your calendar for a week packed with summer excitement! From music on the Bay and all-you-can-eat brunches to art shows, crab feasts, and outdoor concerts, there's no shortage of ways to celebrate the season. Cruise the Chesapeake aboard the Wilma Lee, jam out with Tantric, support inspiring causes like Hop on A Cure, and discover local talent at galleries and farmers markets. Whether you're in the mood for a relaxing tea or a high-energy goth night, this week's events deliver something for every vibe.
Wilma Lee Wednesday Night Races Watch Party
July 23rd; Annapolis Maritime Museum, 5:30pm – 7:30pm, Annapolis
Join our crew for a two-hour extraordinary cruise enjoying the Wednesday Night Races on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda).
Annapolis Opera Presents: Stories Through Music
July 23rd, 24th, 28th, 29th; Crofton Community Library, 6:00pm – 7:00pm, Annapolis
Join the Annapolis Opera House for Stories Through Music, a lively and interactive concert experience designed especially for kids and families. This engaging program introduces young audiences to the magic of storytelling through classical and popular music favorites. Through fun narration, live performance, and audience participation, children will learn how melodies, lyrics, and rhythms come together to tell powerful stories. It’s a perfect way to spark imagination, curiosity, and a love for music — all in an entertaining and educational setting!
GADD Crab Feast
July 23rd; Kentmoor Restaurant, 6:00pm – 8:00pm, Stevensville
Get ready for a night of summer fun at the GADD Crab Feast on [insert date], featuring all-you-can-eat crabs, shrimp, corn on the cob, red potatoes, andouille sausage, Caesar salad, and twice-baked mac and cheese—plus an open bar sponsored by Kitchen & Bath Creations! Enjoy cornhole and other games while networking with fellow GADD members and guests.
DANSE MACABRE II- “Summergoth Edition”
July 24th; Cult Classic Brewing Company, 7:00pm – 10:00pm, Stevensville
On a sweltering summer evening, the wolves howl and the bats flutter over Cult Classic once again for DANSE MACABRE-A Goth Night! Featuring 3 regional artists and a DJ, bring your dancing shoes. Capes and fangs optional.
Chesapeake Bay Paddle
July 26th Kent Island
The Chesapeake Bay is a national treasure as the largest estuary in the United States and 3rd in the world. Our mission is to help protect it by working with Oyster Recovery Partnership to plant more oysters, Chesapeake Conservancy to support their efforts to designate the Bay as a National Park and WaterKeepers Chesapeake to help keep the waters and rivers of the Bay healthy
St. Michaels Farmers Market
July 26th; Downtown St. Michaels, 8:30am – 11:30am Talbot County
The St. Michaels Farmers Market (SMFM) is a non-profit, producer-only farmers market in charming St. Michaels on Maryland’s Eastern Shore, located downtown at 206 South Talbot Street, and taking place on Saturdays from April through November between 8:30 a.m. to 11:30 a.m., rain or shine. After more than 25 years of supporting local farmers and a sustainable food system, the SMFM has become a beloved community ritual, with more than two dozen vendors selling everything from fresh fruit, vegetables, and flowers through farm-raised meat, Chesapeake Bay seafood, baked goods, and more, all certified as grown or made within 60 miles of market. Also expect live music, family-fun activities, and community non-profit pop-ups throughout the year.
A.Y.C.E. BRUNCH @ Cult
July 26th; Cult Classic Brewing Company, 9:00am – 1:00pm, Stevensville
Feast your wallet on the hottest deal in town. CULT CLASSIC introduces an All-You-Can-Eat Brunch from 9am - 1pm every Saturday & Sunday. Load your plate with all the eggs, bacon, sausage and UNCH you can handle. We've also got some waffle-y delicious toppings for your made-to-order waffles. Omelet you finish, but not before you load that lil egg pouch with all the freshest ingredients in the bar. Wash it all down with our Château Cult Mimosas or whatever makes you feel human.
Wilma Lee Heritage Cruises
July 26th; Annapolis Maritime Museum, 1:00pm – 3:00pm, Annapolis
Experience Annapolis and the Chesapeake Bay like never before on this guided two-hour heritage tour aboard the historic Skipjack Wilma Lee. Learn about the city’s history and the ecology of the Bay while viewing landmarks like the Chesapeake Bay Bridge and the Naval Academy. Tour guides will identify and share fun facts about native Chesapeake Bay wildlife along the cruise. Perfect for families and maritime enthusiasts.
Women Artists Show
July 26th; Annapolis Marine Art Gallery 2:00pm - 5:00pm Annapolis
Join three local artists as they display their work! Meet Nancy McPherson, Sharon Littig and Maryellyn Lynott at Annapolis Marine Art Gallery in Downtown Annapolis and celebrate our women artists! Light refreshments provided and all artwork will be for sale. Make a connection, enjoy the exhibit and meet some talented local Maryland artists!
HOP ON A CURE
July 26th; Private Location; 6:00pm – 9:00pm, Chester, MD
Please join Juliet Taylor and Tim Abeska for an intimate private concert with John Driskell Hopkins, founding and active member of Zac Brown Band, and his friends for an evening of music and storytelling at private home on the water in Chester, Maryland (location to be shared with ticket holders). A $500 donation per ticket includes music, a silent auction, dinner, and drinks. 100% of event proceeds go to Hop On A Cure and its mission to support research to prevent, reverse, and cure ALS. Thank you to sponsors Chesapeake Bartenders. In partnership with: Chesapeake Region Accessible Boating (CRAB).
Tantric with Lydia Can't Breathe LIVE at Cult
July 26th; Cult Classic Brewing Company, 7:30 – 11:00pm, Stevensville
Louisville-based post-grunge rockers Tantric bring their signature groove-heavy sound and high-energy performance to Cult Classic Brewing. With 15+ years of hits and six studio albums, Tantric delivers guitar-rich rock with powerful vocal harmonies and an unpredictable edge. Come early for cold drinks, house-brewed beers, and fresh eats like handmade pizza, burgers, and wings.
Brampton's Elegant Afternoon Tea
July 27th; Brampton Inn, 2:00pm – 3:30pm, Chestertown
Join us for an elegant afternoon of fine food and drink, and wonderful conversation! Our pastry chef’s creations of decadent sweet and mouth-watering savory bites are paired with a hand-picked selection of fine Harney & Sons Teas including iced tea in the warmer months. Enjoy as you and your companions spend a lovely afternoon in the peaceful elegance of the Brampton.
Summer Concert Series:
Waugh Wednesdays: Summer Concert Series - July 23rd; Waugh Chapel Town Center: The Josh Christina Band
Thursdays in the Park – July 24th; Queen Annes County Center for the arts: Red betty and the Ruckus
Tides & Tunes – July 24th; Annapolis Maritime Museum: The Grilled Lincolns
ATC Summer Concert Series – July 25th; Annapolis Town Center: Groove Spot Band and Show
Free Avalon Outdoor Concert Series – July 26th; Avalon Theatre: US Navy Band cruisers
Bayside Summer Concert Series – July 27th; Downs Park
Allen Pond Summer Concert Series – July 27th; Allen Pond Park: Ambience
Tunesday: Summer Concert Series – July 29th; Back Creek and Second Street in Eastport: Luke Borchelt
