Chesapeake Fall Festivals for Sailors

Sailors Get Festive on the Chesapeake Bay in Fall 

Somewhere between the end of the sailing season and the holidays, you’ll find fun fall festivals for the whole family along the Chesapeake Bay. Here are two sailors’ favorites on the Eastern Shore:

downrigging fireworks
It doesn't get more scenic than watching fireworks above illuminated tall ships at the Sultana Downrigging Festival. Photo by Eric Moseson

Tall Ships and Bluegrass in Chestertown

Rather than mourn as they took down the sails and tucked away their tall ships and other vessels for winter, the folks at the Sultana Education Foundation decided instead to celebrate the season with fellow sailors, live music, art, and history at the Sultana Downrigging Weekend, October 31 to November 2, on the waterfront at historic Chestertown, MD. What started as an interesting pairing of tall ships and top-notch bluegrass music has become a beloved autumn tradition with activities for the whole family.

The schedule includes tall ship tours on AJ Meerwald, Godspeed, Kalmar Nyckel, Maryland Dove, Lady Maryland, Pride of Baltimore II, Lynx, Sultana, and Sigsbee. Festival attendees can also expect public sails, a Halloween party, a tall ship parade, music and more bluegrass music, vendors, and fireworks.

The inaugural public presentation of “Sultana, a Geographic History” will take place on Sunday, November 2 at 11 a.m. Sultana Education Foundation’s Chris Cerino will lead you through the history of the 1768 Royal Navy Schooner Sultana as she traveled the Atlantic Coastline between 1768 and 1772 enforcing the hated British tea taxes. Particular focus will be given to Sultana’s travels on the Chesapeake and Delaware Bays, including the schooner’s visit to George Washington’s Mount Vernon where her captain, John Inglis, dined with the future President.

This presentation takes advantage of the Sultana Education Foundation’s innovative Swain GIS Theatre, which projects images and animations on a 1000-square-foot, high-resolution map of the Chesapeake Bay and Mid Atlantic. (The presentation is limited to 75 participants on a first-come-first-served basis.)

tall ship sailing
Public sails on tall ships and classic sailing craft on the Chester River in Chestertown, Maryland, Chesapeake Bay. Photo by Eric Moseson

Among the “book talks” to tune into, SpinSheet co-founder and local author David Gendell will discuss his book “The Last Days of the Schooner America” at 1 p.m. on Saturday, November 1. At 3 p.m. Thomas Guay will talk about his new novel “Chesapeake Bound,” and Duncan Hood will present about the Great Chesapeake Bay Schooner Race.

Exhibits include works by Eastern Shore painter Marc Castelli, a model boat and ship display, and “Blacks on the Water.” The log canoe Silver Heel and Cocktail Class wooden race boats will be among the in-water exhibits, with racers on hand to talk about the history of the boats and the racing scene.

Bring the kids! The festival is family-friendly and provides many activities for young people: touring ships, making sailors’ hats, a “children’s buoyancy challenge” (building boats with materials such as popsicle sticks, foil, and duct tape), more crafts, and a petting zoo.

All festival proceeds benefit the Sultana Education Foundation, which provides hands-on educational opportunities that promote stewardship of the Chesapeake Bay’s historic, cultural, and environmental resources. By helping students of all ages develop an appreciation for the Chesapeake Bay, Sultana is working to create a community of individuals who are dedicated to preserving this irreplaceable treasure. Learn more at sultanaeducation.org; find the full festival schedule at downrigging.org.

Celebrating Eastern Shore Heritage and Art

For three days every November, nearly 20,000 visitors discover the best of local wildlife, nature, art, heritage, food, and fun at the Waterfowl Festival in Easton, MD. While strolling along the lovely streets of Easton from November 14-16, visitors can discover a tradition that has been going strong for generations.

waterfowl festival
Even if it's in town rather than on the waterfront, sailors enjoy strolling, art exhibits, and kids' activities among other activities at the Waterfowl Festival in Easton, Maryland.

Art collectors find exceptional wildlife art from renowned master artists, along with a variety of events and vendors for all to enjoy that display fishing lures, all-terrain vehicles, boats, and much more. Those looking for entertainment can take in retriever demonstrations, Dock Dogs competitions, goose and duck calling contests, and street musicians. Kids activities include a kids’ calling competition and decoy painting. Holiday shoppers can find unique items for everyone on their list. After an afternoon of fun and exploration, visitors can sample Eastern Shore cuisine.

From its founding in 1971, the Waterfowl Festival has been able to not only share the unique Eastern Shore heritage with visitors but also help to preserve it. More than $6 million in proceeds has been given away through grants for environmental, conservation, and education projects throughout the DelMarVa Peninsula to preserve wildlife, waterfowl, habitat, and heritage for future generations.

The Waterfowl Festival is cashless, so bring your credit cards to the ticket booth. Learn more at waterfowlfestival.org.

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