Festival Highlights

Downrigging features four days of Chesapeake maritime experiences both on and off the water, from tall ship sails, deck tours, concerts, lectures, films, and exhibits to 5k’s and family activitiesHere are just a few of the exciting events you can look forward to at Downrigging 2018.

Tall Ship Tours and Sails

Experience four centuries of sail at Downrigging Weekend, 2018 on a fleet of ships and wooden boats including KALMAR NYCKEL, VIRGINIA, LYNX, SULTANA, LADY MARYLAND, SIGSBEE, ELSWORTH, and more. Free tours of the vessels are available during select hours on Friday, Saturday, and Sunday, and visitors will have four opportunities throughout the weekend to take a public sail on SULTANA or other visiting tall ships.


In Partnership With

Fireworks and Ship Illumination 

Downrigging Weekend’s festivities kickoff with a free annual fireworks display and ship illumination event on Friday, 7:00 PM.  The Tall Ships will also be illuminated on Saturday and Sunday evenings.  Fireworks and lights are best enjoyed from Chestertown’s waterfront, but please note that the docks at the Chestertown Marina close at dusk.

Sponsored by

Lectures and Presentations

Maritime-focused talks are offered free to the public throughout Downrigging Weekend. This year’s schedule includes talks by:

  • John Brady, President and CEO of the Independence Seaport Museum
  • Vince Leggett, founder of the Blacks in the Chesapeake Foundation
  •  Jacques Baker, author of Gilbert Byron, a Life Worth Examining

In Partnership With

Music and Concerts

Rock out to a slate of regional acts at a series of family-friendly free public concerts, featuring performances by:

In Partnership With

Dock Dogs

On Saturday and Sunday is the popular Delmarva Dock Dogs competition hosted by Kingstown Farm, Home and Garden, where dogs from all over the region compete to see who can leap the furthest. Local dog owners are welcome to enter their own dogs in the competition!

Registration and scheduling information can be found a the Kingstown Farm, Home and Garden Website.

Partner Event With:  

Classic Cars and Boats

On Saturday and Sunday, check out dozens of vintage cars and classic runabouts from private collections at the foot of High Street, brought to you by the Antique and Classic Boat Society.  The event is free to the public.

In Partnership With

Chester River Challenge

Join ShoreRivers for its annual Chester River Challenge 5K and Half Marathon which supports habitat restoration projects, advocacy efforts, and water quality monitoring programs on Maryland’s Eastern Shore.


Partner Event With

Other Downrigging Activities

Join the Sultana Education Foundation and other local businesses and nonprofits for additional downtown events running throughout the festival.  Here is a short list