Chesapeake Bay Maritime Museum
CBMM will host its annual Charity Boat Auction on Saturday, Aug. 30
As summer winds down, the Chesapeake region is buzzing with events you won’t want to miss. This week brings everything from wine tastings and live music to science talks, garden strolls, and even a classic rock concert with Lynyrd Skynyrd. Whether you’re looking for a laid-back evening with charcuterie and friends, a chance to learn something new about local wildlife, or the excitement of a boat auction and big outdoor concerts, there’s something happening every day. Take a look at what’s on the calendar and start planning your weekend now—you’ll find plenty of ways to relax, connect, and make the most of these late-August days.
Wednesday Wine Down (4th Wednesdays at CULT)
August 27th; Cult Classic Brewing Company, Stevensville 6:00pm – 8:00pm
It's Wednesday night, you're trying to relax, and we've got everything you need. Assemble your crew (or come as a free agent) and join us for our monthly sampling flight of 4 wines as well as a pour of your favorite. We'll have a charcuterie board and a whole performance room to unwind in. Guests must be 21+ years of ago to attend ('cause wine). Doors open at 6pm. Wine flights and charcuterie are served at 6:30pm. Each guest will receive a ticket for an additional pour of their favorite wine.
Charcuterie for a Cause
August 28th; Sunrise of Annapolis, Annapolis 2:00pm – 4:00pm
Indulge in a decadent afternoon of delicious bites and heartfelt purpose at “Charcuterie for a Cause”—a delightful fundraiser held under the tent at Sunrise of Annapolis. Enjoy beautifully curated charcuterie boards and refreshments/brunch-style delights while connecting with your community and supporting those in need. All proceeds benefit a worthy local cause, blending culinary flair with meaningful giving in a memorable setting.
Annapolis Science Cafe @ 49 West: Conserving Maryland’s Farmland Raptors, by Alex Pellegrini
August 28th; 49 West Coffeehouse, Annapolis 6:00pm – 7:15pm
Alex Pellegrini is a Research Technician at Patuxent River Park, and the Farmland Raptor Program Coordinator with the Maryland Bird Conservation Partnership. In this role, he manages statewide nest box programs and leads several research initiatives focused on grassland raptor conservation. His work also includes collaborations with the Global Owl Project, the Global Short-eared Owl Working Group, and Project Owlnet, contributing to research on owl taxonomy and migration. We hope you will join us at the Annapolis Science Café at 49 West, but Zoom is also available. It's best to reserve seats for this event by calling 49 West at 410-626-9796. The event is free but you need to buy something from the restaurant.
Guided Garden Stroll
August 29th; William Paca House and Garden, Annapolis 9:30am – 10:15am
Take a stroll through our beautifully restored two-acre 18th century English garden. Painstakingly restored to its original splendor using details drawn from historic artwork and archaeological excavations, the colonial William Paca Garden is a picturesque retreat from the bustle of the city. Your experienced docent will share its history from the time of William Paca, signer of the Declaration of Independence, to present day as you wander the terraced landscape, formal parterres, wilderness garden, the practical kitchen and medicinal gardens, and orchard. The charming Summerhouse beckons visitors to cross the latticework bridge over a fish-shaped pond.
Adam Forbes Performing Live at Captain's Daughter
August 29th; Captains daughter, Annapolis 5:00pm – 7:00pm
Get ready for an unforgettable night of music and mood—Adam Forbes is performing live at Captain’s Daughter, bringing laid-back vibes and melodic charm right to the bar’s cozy stage. Whether you're winding down your week or simply craving a live soundtrack to your evening, his smooth guitar and soulful selections set the perfect tone. It's the ideal way to enjoy the sounds of summer—with a cocktail in hand and great company nearby.
Charity Boat Auction
August 30th; Chesapeake Bay Maritime Museum, Talbot County 8:00am – 1:00pm
CBMM will host its annual Charity Boat Auction on Saturday, Aug. 30, inviting guests to its waterfront campus to bid on donated vessels of all shapes and sizes in support of its mission. A Labor Day weekend staple for more than two decades, the Charity Boat Auction is the flagship event of CBMM’s Charity Boat Donation Program, which accepts and sells gently used boats year-round. Every sale directly supports CBMM’s mission to explore and preserve the history, environment, and culture of the entire Chesapeake Bay region and make this resource available to all.
Pops in the Park at Downs Park
August 30th; Downs Memorial Park, Pasadena 11:30am – 1:00pm
This Labor Day weekend, bring your friends, family, favorite date to Anne Arundel County’s best-loved end-of-summer tradition: Pops in the Park with the Annapolis Symphony Orchestra at Quiet Waters Park! As the largest and oldest performing arts organizations in Anne Arundel County, the Annapolis Symphony Orchestra looks forward to Pops in the Park year after year. Enjoy a FREE outdoor concert full of energy, movie music, patriotic favorites, and unexpected surprises - the perfect way to end summer right.
Pops in the Park - Quiet Waters Park
August 31st; Quiet Waters Park, Annapolis 5:30pm – 7:00pm
As the largest and oldest performing arts organizations in Anne Arundel County, the Annapolis Symphony Orchestra looks forward to Pops in the Park year after year. Enjoy a FREE outdoor concert full of energy, movie music, patriotic favorites, and unexpected surprises - the perfect way to end summer right.
Ahmed Warshanna Presents…Ishta!
August 30th; Maryland Hall for the Creative Arts, Annapolis 7:00pm – 9:00pm
Experience modern jazz in an intimate setting with Ahmed Warshanna’s sextet band "Ishta!" performing live at Maryland Hall. A Baltimore-based guitarist, composer, and arranger, he leads the dynamic sextet Ishta!, known for its fiery interplay and genre-defying sound.
Lynyrd Skynyrd is Coming to The HALL at Live! Casino & Hotel Maryland
August 31st; Live! Casino & Hotel, Columbia 7:00pm
Rock and Roll powerhouse Lynyrd Skynyrd is coming to The HALL at Live! on Sunday, August 31! Enjoy an evening of timeless classic rock standards including “Free Bird,” “Sweet Home Alabama,” “Simple Man,” “What’s Your Name” and many more.
Summer Concert Series:
Free Avalon Outdoor Concert Series – August 30th; Avalon Theatre: Delmarva Big Band
Allen Pond Summer Concert Series – August 31st; Allen Pond Park: Voice 24/7
