Sultana Downrigging Weekend Tall Ship and Wooden Boat Festival

Wooden boat festival lures boaters to Chestertown, Maryland

By Susan Gilbert

The Sultana Downrigging Weekend Tall Ship and Wooden Boat Festival in Chestertown, Maryland, has become a favorite fall mini-getaway for my husband and me. In 2018, we took our third trip to this charming town to view interesting ships, Chesapeake Bay work boats, beautifully preserved Chris-Craft powerboats and antique cars.

Sponsored by the Sultana Education Foundation, the festival takes place on the banks of the Chester River. Proceeds from the three-day event support the schooner Sultana. Each year Sultana takes more than 4,500 students from many Maryland ports onto the Chesapeake Bay for hands-on programs in environmental science and history.

During the festival, boaters can enjoy sailing on a tall ship or a restored skipjack, watching the crab boat races, or viewing the restored boats—in and out of the water.

In past years we’ve sailed on the Pride of Baltimore II and the Meerwald, an oyster schooner built in New Jersey. This year we got tickets to sail on the Kalmar Nyckel, a beautiful replica of the first Swedish ship to arrive in Colonial America.

Unfortunately, Saturday morning dawned rainy and windy. We set off hoping for the best, but it wasn’t to be. The other ships sailed, but Kalmar Nyckel did not. Too tall above water, the ship was feared to be unable to maneuver well in the tight quarters of the Chester River in 25- to 35-mph gusts.

Despite the rain and not being able to sail, we found the Chester River shore area much improved. Gone were the muddy paths leading to the docks; now, stable, level pavers provided accessibility for everyone. A beautiful new building replaced the tent that once housed the festival information center. The food, beverage and music tent, which features seafood and bluegrass music, had a new location with a paved path leading into it.

From the harbor, a short walk up tree-lined streets takes you to shops and restaurants in the main part of town. The farmers and artisans market can be found in the green area in the middle of town. It’s easy to be lured there by smells of home-baked goods. You can find locally produced jams and jellies, wonderful skeins of local wool, and many local artisan products. Chestertown has a variety of bed and breakfasts for anyone who wants to stay for more than one day of the festival.

After walking into town in the rain with no sign of the weather clearing, we decided to head home. However, on the way home we heard from friends that the Maritime Museum in St. Michael’s was having its annual Oyster Festival that same weekend. A big hot bowl of oyster stew sounded wonderful, so off we went to the next adventure.


A lifelong boater, Susan Gilbert began fishing with her dad as a young child on lakes and rivers throughout the South. She has recently crewed on a catamaran up and down the Intracoastal Waterway and to the Bahamas. Susan and her husband, Bob, enjoy living on and exploring the shores of the Chesapeake Bay. She is currently assistant administrative officer for Annapolis Sail & Power Squadron/5. This article first appeared in the squadron newsletter, Anchor Watch.

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