Exhibit Your Boat at Downrigging

This page contains information for owners who wish to exhibit a wooden boat at Downrigging Weekend.
If you have a non-wood boat you would like to bring to Downrigging Weekend please contact the Chestertown Marina at 410-778-3616. 
Please read this entire page and then begin the registration process by following the link at the bottom. 

Exhibit Your Vessel

Private owners of wooden boats are invited to bring and exhibit their vessels in the water alongside the Tall Ships assembled in Chestertown for Downrigging Weekend.  Over the years Downrigging Weekend has built up an impressive fleet of private boats and the festival has proven to be a great venue to meet other wooden boat enthusiasts.

Requirements for Exhibit Vessels

  • Vessels must be a wooden boat (of any era) or a facsimile of a wooden boat design from the 1960’s or earlier.
  • Vessels (with the exception of trailered boats) must attend the entire festival from Friday afternoon, October 27, through at least Noon on Sunday, October 29. You are welcome to go out sailing/cruising during your stay.

Day Boats on Trailers

If you have a small wooden boat that you would like to launch from a trailer and keep in the water for the day, this is possible.   Limited reserved trailer and vehicle parking is available. Limited bulkhead space for daytime docking is also available.  Once you register your vessel the Harbor Master can discuss specifics with you.

Docking Facilities

Downrigging Weekend makes use of the entire Chestertown Waterfront for docking.   Docking space ranges from full service slips to basic bulkhead space. To keep things simple the Slip and Event Fees are identical regardless of the type of docking you have, so we recommend that you register early to get the best docking space. Once you register your vessel, the Harbor Master will discuss available options with you before any payment is required.

Click Here to See the Harbor & Docking Plan as of August 25, 2016

Slip & Event Fees

Slip and event fees are listed below.

Boat Length Fee
All Vessel Lengths (due to the condition of the Chestertown Marina we have reduced slip fees) $60
At Anchor or Private Slip (no slip provided) $40
Trailered Vessel (includes ramp fees) (no slip provided) $40

All fees include:

  • Two (2) nights of dockage on the Chestertown waterfront at a mutually agreeable location (this does not apply to vessels at anchor, in private slips or arriving by trailer).   Vessels in slips may stay through Monday morning for no additional charge.
  • Two (2) Dinner Tickets for exclusive Saturday Night Captains’ Dinner beginning at 6:30pm in the festival tent behind the Fish Whistle Restaurant. Additional tickets are available for your crew at $10 each.
  • One (1) Downrigging Weekend limited addition, long-sleeved T-Shirt. Additional T-Shirts are available for your crew for $20 each.

Working Around the Tall Ships

Because some docking locations are inboard the visiting Tall Ships, you may have to time your arrival and departure around the sailing schedules of the Tall Ships.  This is particularly true if you have a mast or tall superstructure.   When you register your vessel the dock master will tell you about any possible restrictions before you make your payment.

Please note the following public sailing times when all of the larger ships will be away from the dock.

  • Friday, October 27 / 3:00-5:00pm Public Sail – Larger private vessels should plan to arrive during this window.
  • Saturday, October 28 / 10:30am-1:00pm Public Sail – This is a great time to go out cruising and see the Tall Ships under sail.
  • Saturday, October 28 / 2:30-5:00pm Public Sail – This is a great time to go out cruising and see the Tall Ships under sail.
  • Sunday, October 29 / 1:00-3:30pm Public Sail – If you need to leave Sunday, this is the time to go.
  • Monday, October 30 / Tall Ships Depart Early Morning – Weather permitting, the Tall Ships usually depart between 6:00 and 11:00am.

Registering and Reserving Dockage

Registering you boat is as quick as three easy steps . . .

Step #1:  Follow the link below to submit basic information about your vessel.  This only takes a couple of minutes and will help us determine what docking/exhibit options are available for you. This does not commit you!


Step #2:  After reviewing your information the Harbor Master will contact you via email/phone to discuss possible docking options and review pricing.

Step #3:  Once a slip/space has been agreed on, the Harbor Master will send you a link where you can pay your slip and event fees online.  Only after you have paid your fee is your slip confirmed.


We are pretty generous about cancellations and refunds.  That said, please don’t reserve a slip unless you are truly committed to attending and let us know as soon as possible if your plans have changed.