Downrigging Weekend in Chestertown, MD

August 27th, 2022

Downrigging Weekend in Chestertown

Are you ready to explore history, listen to exciting live music, and have fun with your family and friends? One of the most interesting things to do in Maryland is attending Sultana’s Downrigging Festival in Chestertown. Keep reading to learn more about this fantastic festival!

Where is Chestertown?

Chestertown is a small, friendly community located on the scenic eastern coast of Maryland. The town is on the shore of the Chester River, which feeds into the Chesapeake Bay. The area has some of Maryland’s most beautiful natural landscapes, with gorgeous waterfront views, amazing natural wildlife, and colorful scenery.

While the community only has around 5,000 residents, it is full of art, entertainment, culture, and outdoor recreational opportunities. You’ll love the downrigging weekend in Chestertown!

What is the Sultana Downrigging Festival?

The Sultana Education Foundation’s Downrigging Weekend Festival, or Sultana’s Downrigging Festival for short, happens annually in Chestertown, Maryland. The festival, which typically occurs in October or November, features many fun and educational events that celebrate the history of the Tall Ships, the fascinating small-town Maryland, and much more!

The history behind the festival will appeal to boaters, nature-lovers, and all history buffs. Years ago, the Tall Ships Sultana and Pride of Baltimore II finished their sailing season by visiting the Chester River. The ships would soon be “downrigged” for the season, or done sailing. Awed by the beautiful scenery of the Chestertown area, the captains of the ships decided that a celebration needed to be dedicated to the end of the season in this area annually. From there, the Sultana Downrigging Festival was born! This year it is set to take place October 28-30, 2022.

What Events Are at the Festival?

There is a wide variety of events that happen at the festival, which is perfectly suited to the wide variety of festival goers who come from all over the world. You’ll have the chance to explore Chestertown and small-town culture, experience sailing and Maryland history, spend time with your family and friends, appreciate live music, and by food from local vendors. The opportunities are endless!

Explore Chestertown

One of the best things to do in Maryland is to explore the many small communities. This festival is perfect for enjoying the small-town lifestyle while experiencing big-town fun. Some of the festival events are created mainly for exploring Chestertown and appreciating small-town culture.

While at the festival, you can navigate the town’s streets as you visit the many exhibits throughout the area. Or, learn about the area by visiting the Chesapeake Roving Ranger, which will teach you about local Chesapeake Bay and Chester River wildlife. You might consider attending the annual parade through Chestertown which features classic parade favorites, including big floats, lots of candy for your children, and fun entertainment, or, choose to explore the Chester River with the River Packet cruises.

Experience History

If you’re interested in history, you will fall in love with the downrigging festival. The festival features history about sailing, the War of 1812, Chestertown and the Chesapeake Bay, and more. For example, the tours of the Tall Ships introduce you to the historical ships, including the Sultana, Pride of Baltimore II, the Virginia, and other Tall Ships.

The festival features other historical exhibits as well. Although some exhibits cycle in and out throughout the years, typically you can:

·        Visit the Log Canoe Silver Heel Exhibit to see one of the few remaining historic Chesapeake Bay log sailing canoes

·        See antique American classic speedboats with the Antique and Classic Boat Society

·        Learn about the fascinating real-life history of Maryland during the War of 1812 with the War of 1812 Interpretative Encampent

·        View art exhibits featuring famous artists

Spend Time with Family

Are you looking for a weekend getaway to spend time with your family? The downrigging weekend in Chestertown is the perfect opportunity to enjoy time with your family and friends. Most of the activities are family-friendly and interactive, so even your youngest children will stay interested and entertained.

The annual parades are a great way to start off your weekend. Spend time together as you watch the Tall Ships sail into the port, or visit downtown Chestertown to watch floats go by. The Music Festival Village and Vendors also open on the first day of the festival. Bring your family to the village grounds and enjoy fresh local food and relax by a warm fire as you listen to live music. Finally, end your nights by watching the fireworks displays the festival puts on!

Appreciate Live Bluegrass Music

Do you love the sound of live music? This festival is perfect for you! The annual downrigging festival always features an assortment of live bluegrass music. The music is upbeat and fun to listen to. The artists are often local, and are handpicked by the festival board for their amazing talent.

When you’re at the festival, go to the Music Festival Village to eat a warm meal and enjoy the bluegrass music. The festival has someone performing at almost all hours of the day. In 2021, the festival featured some of the country’s finest bluegrass artists, including Kid Davis and Company, No Part of Nothin, and Danny Paisley and Southern Grass.

Buy From Local Vendors

If you love eating delicious food and supporting local businesses, you’ll enjoy everything that the Music Festival Village and Vendors has to offer. Each year, several local vendors set up in the Music Festival Village to offer a delicious, fresh and hot meal for festival goers while live music is playing.

Some regular dining options at the festival include local Maryland seafood, such as 2021’s J.A. McCown Oysters. If you’re interested in relaxing with a delicious coldbrew or glass of wine, Microbrew and Wine Truck often visits the festival. Other food vendors have American classics, including pizza, burgers, and fries. You won’t be able to resist the festival’s food!

Experience the Festival Year-After-Year

Are you interested in experiencing the downrigging weekend for yourself? The best way to experience the festival year-after-year is to make Chestertown your new home. Contact the Sutton Team to find your perfect property! For more on downrigging, check out their site at


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