Children’s Music: Dan & Claudia Zanes October 29, 2022 / 11:30am-1:30pmDavis Parking Terrace at Sultana’s Holt Education Center, 200 S. Cross St. A kid’s concert the likes of which Chestertown has never seen! Join Grammy and Parents Choice Award winner and NPR darlings  Dan & Claudia Zanes as they bring their high energy, educational and rocking […]

Book Talk: Peter A. Jay Timepieces October 29, 2022 | 2:00pm – 3:00pmThe Retriever Bar | 337 1/2 High St.  As Peter Jay’s Timepieces makes clear, occasional blog posts are no substitute for the collected newspaper columns of an astute observer whose sustained curiosity, distinctive perspective and dry humor can be crafted into such a […]

Book Talk – Greg Melville Over My Dead Body October 29, 2022 | 11:00am-12:00pmThe Retriever Bar | 337 1/2 High St.  Melville’s Over My Dead Body is a lively (pun intended) and wide-ranging history of cemeteries, places that have mirrored the passing eras in history but also have shaped it. Cemeteries have given birth to […]

Family Fun – Sumner Hall What’s in the Ditty Bag? October 29, 2022 | 10:00am-1:00pmSumner Hall | 206 S. Queen Street The young and young of heart are invited to drop in at Sumner Hall to find out! (Hint: there may be knots to tie, stories to hear, a sea shanty or two, a historic […]

Book Talk: Phillip Greene To Have & Have Another CANCELLED October 28, 2022 | 5:30-6:30pmThe Retriever Bar | 337 1/2 High Street Philip Greene, cocktail historian, spirits consultant, and cofounder of the Museum of the American Cocktail, offers us a view of Papa through the lens he preferred—the bottom of a glass. Greene will deliver […]

Marc Castelli – Artist Talk October 29, 2022 | 10:00am & 1:00pmMassoni Art | 203 High Street Join renowned artist Marc Castelli for coffee as he shares his new collection of watercolors of the Chesapeake Bay, “Paralian.” This is a rare opportunity to interact with a master artist at the peak of his craft. MassoniArt

Marc Castelli Exhibit – Paralian October 28, 2022 | 5:00-7:30pmOctober 29, 2022 | 10:00am-5:00pmOctober 30, 2022 | 11:00am-3:00pmMassoni Art | 203 High Street Marc Castelli’s annual show at Massoni Art has become a Downrigging tradition. Expect to see exquisite and informed renderings of watermen, workboats, and log canoes from a painter recognized as one of […]

2022 In-Water Exhibit Vessels At the Chestertown Marina All WeekendDocks Open from Dawn to Dusk Joining the Tall Ships visiting Chestertown for Sultana Downrigging will be a handful of privately owned wooden boats, including “buy boats,” historic yachts, and sailing craft both large and small. The festival welcomes application from boat owners interested in exhibiting […]

Cocktail Class Racers with CCWBRA Cocktail Class Wooden Boat Racing AssociationOctober 29, 2022 | 9:00am – 5:00pmOctober 30, 2022 | 10:00am – 3:00pmChestertown Waterfront In addition to Tall Ships and Antique Boats, the marina will also host a selection of incredibly nifty 8-foot racers called a “SKUA”, an 8 ft. plywood skimmer designed in 1939 […]

Skip Finley Whaling Captains of Color America’s First Meritocracy October 30, 8:00pm The Garfield Center, 210 High St. Free / Limited Seating Many of the historic houses that decorate Skip Finley’s native Martha’s Vineyard were originally built by whaling captains. Whether in his village of Oak Bluffs, on the Island of Nantucket where whaling burgeoned, […]