Watching fireworks over a historic harbor filled with Tall Ships while listing to great bluegrass music – what could be better? Fireworks are shot from Wilmer Park, making the Chestertown Marina, and particularly the Downrigging Festival Village (ticket required) an ideal viewing location.
There is nothing quite like seeing the Downrigging Fleet illuminated along the Chestertown waterfront – for many visitors it is a highlight of the festival!
Saturday, November 2 | 9:00am-5:00pm
Sunday, November 3 | 10:00am-4:00pm
Partner: Antique and Classic Boat Society of the Chesapeake Bay
On Saturday and Sunday the Chestertown waterfront will be brimming with speedboats from America’s golden age. Organized in partnership with the Antique and Classic Boat Society of the Chesapeake, this exhibit will feature some of the finest antique boats around.
Pam Ortiz Band
Garfield Center | 210 High Street, Chestertown
Saturday, November 2 | 7:00pm
Tickets: $15
Partner: Garfield Center
The Pam Ortiz Band returns, by popular demand, for their 7th Downrigging Concert at the Garfield Center for the Arts at 7 PM on Saturday November 2nd. The show will feature original songs Pam has written for “Downrigging” and old and new tunes celebrating water, sailing and the maritime tradition. And of course, you won’t want to miss the return of the Dawson’s Blue Whale which brought the house down when it last appeared in 2017. The concert is sure to be a night of friends old and new and a celebration of the “Good Ship Sultana.”
Friday, November 1 | 4:30-5:00pm
Saturday, November 2 | 12:30-1:00pm | 4:30-5:00pm
Sunday, November 3 | 3:00-3:30pm
Come down to the waterfront and view the Tall Ships as they make their way back to Chestertown following their sails. This isn’t a formal parade, but you will get a great look at all of the ships underway.
Friday, November 1 | 12:00-5:00pm
Saturday, November 2 | 9:00am-5:00pm
Sunday, November 3 | 10:00am–4:00pm
Partner: National Park Service & Chesapeake Conservancy
Pay a visit to the Chesapeake Roving Ranger—the mobile visitor center for the National Park Service Chesapeake Bay office—to get a National Park passport stamp, participate in an interpretive program, and learn about new experiences in the Chesapeake watershed.
Friday, November 1 | View the Fleet Cruise | 6:00-8:00pm | $40
Saturday, November 2 | Fireworks Cruise | 7:00-9:00pm | $60
Sunday, November 3 | Brunch Cruise | 11:00am-1:00pm | $30
Sunday, November 3 | Supper Cruise | 4:00-6:00pm | $30
Departing from the Foot of High Street
Cruise the Chester River in style onboard Chestertown’s own River Packet. The River Packet is offering four cruises during Sultana Downrigging, including a Fireworks Cruise on Saturday evening. Great food and drink are available on board. Please purchase tickets directly from the Chester River Packet Company using the link above.
Saturday, November 2 | 9:00am-5:00pm
Sunday, November 3 | 11:30am-3:30pm
Come see the Log Canoe Silver Heel – one of approximately 20-25 surviving traditional Chesapeake Bay log sailing canoes, which were the primary fishing craft of the Bay for hundreds of years. She is now operated by the Silver Heel Foundation, dedicated to preserving and promoting the tradition of log canoe sailing through education and outreach.
Saturday, November 2 | 10:00-11:00am
Partner: Massoni Art
Join renowned artist Marc Castelli for coffee as he shares his new collection of watercolors of the Chesapeake Bay.
Castelli’s King’s Tide
Friday, November 1 | 5:00-7:70pm
Saturday, November 2 | 10:00am-5:00pm
Sunday, November 3 | 11:00am-3:00pm
Partner/Tickets: Massoni Art
Marc Castelli’s annual show at Massoni Art has become a Downrigging tradition. Expect to see incredible renderings of watermen, workboats, and log canoes from a painter recognized as one of the finest marine artists in the country.
1:00pm | Saturday, November 2
Partner: The Bookplate
During this talk at The Book Plate, Brian Hope – author, artist, retired bay pilot, and founder of Project Liberty Ship in Baltimore – will discuss his new book “Bay Pilots – A History of the Maryland Pilots Association.” Based in Baltimore, the men and women of the Maryland Pilots apply their hard-earned local knowledge to the safe and intricate movement of ships throughout Chesapeake Bay. Hope brings forty years of experience to the subject, and his stories are full of history, adventure, humor and excitement.
11:00am | Saturday, November 2
Partner: The Bookplate
During this talk at The Book Plate, Tim Newby will explore his new book, “Bluegrass in Baltimore – The Hard Driving Sound and its Legacy.” With an influx of Appalachian migrants who came looking for work in the 1940s and 1950s, Baltimore found itself populated by some extraordinary mountain musicians and was for a brief time the center of the bluegrass world. Life in Baltimore for these musicians was not easy. There were missed opportunities, personal demons and always the up-hill battle with prejudice against their hillbilly origins. Based upon interviews with legendary players from the golden age of Baltimore bluegrass, this book provides the first in-depth coverage of this transplanted-roots music and its broader influence, detailing the struggles Appalachian musicians faced in a big city that viewed the music they made as the “poorest example of poor man’s music.”
Chestertown Marina Office | 207 S. Water St, Chestertown
Friday, November 1 | 5:00-6:30pm (opening reception)
Saturday, November 2 | 10:00am-4:00pm
Sunday, November 3 | 10:00am-4:00pm
Partners | Kent County Arts Council, Arts-in Motion
Join the Kent County Arts Council and Arts-in-Motion for an exhibit of student art focusing on African American maritime history during the Revolutionary War. This eclectic, mixed-media display was created by the combined 8th grade classes of Kent County Middle School, The Kent School and Radcliffe Creek School. The exhibit is curated by Jason Patterson, Artist-in-Residence with the Kent County Arts Council and fellow at the C.V. Starr Center for the Study of the American Experience.
Chestertown Marina, 207 S. Water St.
9:00 am | Saturday, November 2
Partner: Shore Rivers
Join Shore Rivers for its revamped Run for Clean Rivers 5K and 10-miler! Spend your Saturday morning of Sultana Downrigging with your Chester Riverkeeper and friends of ShoreRivers. The race will start and end at the brand new Chestertown Marina, overlooking the beautiful waterfront.
Help Shore Rivers raise money for their restoration projects, advocacy efforts, and water quality monitoring programs on the Chester, Sassafras, Miles, Wye, and Choptank rivers. After your morning run, enjoy beer, food, and entertainment while the tall ships take sail.
Saturday, November 2 | 10:00am
Partner: Chestertown Lions Club
Before you go sailing (or listen to bluegrass!) stop by and take in Chestertown’s Annual Halloween Parade, sponsored by the Chestertown Lions Club. It’s a classic small-town parade and not to be missed!
