Wildfowl Decoy Exhibit

Chestertown Decoy Museum 217 High Street, Chestertown

Visit Chestertown’s newest cultural attraction, the Chestertown Decoy Museum, to explore a world-class collection of working wildfowl decoys and decorative carvings of waterfowl and shorebirds from throughout the East Coast flyway. During Downrigging […]

Tour the Tall Ships

Chestertown Marina 207 South Water Street, Chestertown

Tour the fleet of ships, schooners and skipjacks assembled in Chestertown for Sultana Downrigging. Deck tours are free, however children under 16 must be accompanied by an adult. Visitors are […]

Sail the Tall Ships

Chestertown Marina 207 South Water Street, Chestertown

Sail the Chester River onboard one of the fleet of ships visiting for Sultana Downrigging. There is nothing quite like seeing the fleet unfurl their sails in unison in such […]

Music Village Open

Music Village 207 S Water Street, Chestertown

Downrigging's musical performances take place in an intimate “Music Village,” that pairs live performances with regional food and drink - all against a waterfront backdrop and Tall Ships. A ticket […]

Music – Barkley Cove

Music Village 207 S Water Street, Chestertown

Barkley Cove was raised on collaborative songwriting and rich vocal harmony, mixing genres of folk, rock, country, and bluegrass to create a distinctively original sound that will linger in your […]

Music – Geraldine

Music Village 207 S Water Street, Chestertown

Geraldine is a roots-based string band bringing songwriting to the forefront, while blending elements of old time, American folk, bluegrass, and alternative country in a distinctive, enthusiastic sound. Anchored by […]

Castelli Exhibit

MassoniArt 113 South Cross Street, Chestertown

Marc Castelli’s annual show at Massoni Art has become a Downrigging tradition. Expect to see incredible renderings of watermen, workboats, and log canoes from a painter recognized as one of […]

Music – Caleb Stine

Music Village 207 S Water Street, Chestertown

Caleb Stine is an American singer/songwriter from Baltimore, Maryland. He plays both solo and with Americana-rockers The Brakemen. His style and intensely personal lyrics has evoked comparisons to Townes Van […]

Tall Ships Illuminated

Along the Waterfront Chestertown

Friday October 30 Saturday October 31 6:00-9:00pm Along the Waterfront Free Come down to the waterfront on Friday and Saturday evenings to see the Tall Ship fleet illuminated on the […]

Freedom Ship

First United Methodist Church 105 N Mill Street, Chestertown

Stories and Songs of Maritime Liberation in the Chesapeake With Marcus Rediker and Karen Somerville October 30 6:15pm First United Methodist Church 105 N Mill Street Free A partner event […]

Freedom Ship

First United Methodist Church 105 N Mill Street, Chestertown

Stories and Songs of Maritime Liberation in the Chesapeake With Marcus Rediker and Karen Somerville October 30 6:15pm First United Methodist Church 105 N Mill StreetFree A partner event with […]

Music – The High & Wides

Music Village 207 S Water Street, Chestertown

The High & Wides play string band music from an alternate timeline, one where Bill Monroe's "Rocky Road Blues" made him an international superstar and the rock'n'roll revolution was led […]

The Rocky Horror Show

Garfield Center for the Arts 210 High Street, Chestertown

The original stage version of the pop culture phenomenon, “The Rocky Horror Show,” will be rocking the stage at the Garfield Center for the Arts (GCA) with three productions during […]

Sultana’s Birthday Party

Music Village 207 S Water Street, Chestertown

Downrigging will feature a variety of events to celebrate the 25th anniversary of the festival’s namesake schooner SULTANA, including an official birthday party on Friday, October 30th at the festival's […]

Fireworks

Chestertown Marina 207 South Water Street, Chestertown

Join us for the annual Downrigging Fireworks show, this year celebrating the 25th birthday of the schooner SULTANA. Please mind your footing around the waterfront and keep a laser eye […]