Sultana Downrigging Weekend in Chestertown, MD: What You Need to Know

Autumn in Maryland means gorgeous fall foliage and unforgettably fun festivals. One of our favorite ways to celebrate the season is by attending the Sultana Downrigging Weekend in Chestertown, MD. This event is one of the East Coast’s most prominent annual tall ship gatherings. Don’t miss the celebration in late October!


What to Expect at Sultana Downrigging Weekend in Chestertown MD

Sultana Downrigging Weekend is one of our favorite annual events in town. Learn more about the festivities below, and get ready to book your trip to Chestertown!

What is Sultana Downrigging Weekend?

During the last weekend every October, Sultana Downrigging Weekend marks the end of the sailing season. 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 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.

Tall Ships and Bluegrass for a Cause

Hosted by the Sultana Education Foundation, Sultana Downrigging Weekend works hard to create stewards of the Chesapeake Bay and bring awareness and appreciation to all that attend. This year, all proceeds will go towards the Foundation’s Environmental Literacy Program. We are honored to celebrate such a fun and historic weekend and everything it stands for.

Things to Do at Sultana Downrigging Weekend

Whether you’re looking for a maritime experience on or off the water, you’re in luck! Known for its “tall ships and bluegrass,” Sultana Downrigging Weekend features a variety of activities, including performances by world-class bluegrass musicians and lectures by nationally recognized authors and filmmakers. Grab a bite to eat in the Festival Village, watch a film, or walk along the waterfront. On Friday night, enjoy a spectacular fireworks display and ship illumination to kick off the celebration.

Of course, there are also opportunities to sail aboard one of the magnificent tall ships. We highly recommend booking your tickets, as sailing along the picturesque Chester River is one of the best ways to experience the great outdoors. Check out the full festival schedule for more details.

How to Get There

During the weekend, expect to see a waterfront packed with ships, schooners, and wooden boats. If you aren’t on a tall ship, Sultana’s Festival Village is the place to be! The village is located at 207 S. Water Street along the Chester River.

Touring the tall ships and enjoying the musical performances are free and open to the public. However, if you wish to go sailing as part of a fleet of majestic tall ships, you will need to reserve tickets in advance. Ticket prices range from $35 to $65.

Close-up of canopy bed with white bedding and canopy, buttery yellow walls, and a desk near two windows with white shears
Reserve Your Room at Brampton Inn

You won’t want to miss three days of fun at the Sultana Downrigging Weekend in Chestertown, MD! Once you’ve purchased your tickets, you’ll need a comfortable place to stay along the Eastern Shore of Maryland. Brampton Inn’s bright and airy accommodations are perfect for a romantic getaway or a weekend with friends. Enjoy a delicious homemade breakfast every morning and a decadent tea time every afternoon. When planning your next trip to Chestertown, find the perfect casual-luxury suite or cottage at Brampton for your exciting Sultana Downrigging Weekend. You’ll love every minute you spend in our charming Inn on the eastern shore. Check availability today


Updated August 2023

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Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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