Once the Cocktail Class powerboat racing reason is done, when the leaves fall from the trees and the Halloween pumpkins become sagged and moldered, there’s one place you’ll always find the Cocktail Class Wooden Boat Racing Association (CCWBRA): the Sultana Downrigging Festival in Chestertown, MD.

cocktail class racer
Pink Lady was built and raced by an 80-year-old breast cancer survivor. See Cocktail Class racers displayed on land and in-water at the Sultana Downrigging Festival, October 31-November 2, in Chestertown.

Small Cocktail Class boats will join tall ships in Chestertown.

Since time immemorial, the CCWBRA has displayed its boats both in the water and on land at the annual tall ships and blue grass festival, which unfolds on the shores of the Chester River. Tradition has given the cocktail racers pride of place to mount their land-side exhibit of boats and motors virtually at the entrance to the docks, which are filled with topsail schooners and 17th century replicas of the ships that settled the Mid-Atlantic. Hardly anyone passes the Cocktail Class exhibit without stopping to look and marvel at the boats' tiny dimensions and dandle tiny children in the cockpits. It’s a great way to spend the last weekend in October. 

Throughout the festival many of the ships take members of the public on day sails down the river and back. Several cocktail racers often accompany them, cutting doughnuts around the seemingly ponderous sailing ships and amusing the passengers.

This year’s contingent of racers-turned-public-relations-ambassadors is led, as it always is, by Tom Kerr, the current Overall National Points Champion and first recipient of the Ancient Mariner Award, along with Grand Poohbah Emeritus Fred Allerton.

The festival is sponsored by the Sultana Education Foundation, an organization dedicated to helping students appreciate the Chesapeake Bay. The weekend celebrates this natural treasure as well as the people of Chestertown. The festival started in 2001 when two schooners, Sultana and Pride of Baltimore II, sailed together down the Chester River before they “down-rigged” for the winter season. Today, the weekend gives attendees a chance to spend time touring a fleet of tall ships in one of America’s best-preserved historic seaports.

by Tulio Vulgaris

Learn more about cocktail class racing.

Learn more about the Downrigging Festival.