Four Fun Sailing Events for the Final Weekend of October

Your weekend sailing fun

Here are four fun and seasonal sailing events that will unfold this weekend for sailors of all stripes and those who want to learn more about sailing.

Downrigging Weekend 2021 by Al Schreitmueller
Downrigging Weekend in Chestertown, MD, the 2021 edition. The event is for sailing and music fans alike. Photo by Al Schreitmueller

Downrigging Weekend: The Sultana Education Foundation's Downrigging Weekend Festival is one of the largest annual tall ship gatherings in North America, and it takes place right on the Chesapeake Bay's Chester River in Chestertown, MD. It features a long weekend (Friday, October 28 to Sunday, October 30) of tall ship sails, tours, live bluegrass music, lectures, exhibits, family activities, regional food, and more. Proceeds benefit the foundation's enviornmental literacey programs and the other nonprofits participating in the festival. Participating vessels: Pride of Baltimore II, Virginia, Lynx, Godspeed, Sultana, Kalmar Nyckel, Maryland Dove, and Sigsbee. Threee free scheduled deck tours will be offered. Sails aboard the ships are also offered with registration.

DC Sail Halloween Regatta
DC Sail's Halloween sailing regatta is a "go" for October 29. Limited spots still available.

DC Sail Halloween Regatta: DC Sail hosts its end-of-the-season Halloween Regatta Saturday, October 29. The regatta is open to members and non-members, and sailors are encouraged to compete in costumes.  Race committe will assist solo sailors with teaming them up the day of the event. Regatta fees include a Bountiful Boooo-fet continental brunch. DC Sail executive director Traci Mead says, "I love, love, love this super fun special event at DC Sail, and it is the first time we're hosting it since pre-Covid. There will be so much fun to be had! Whlie the NOR called for registration to close October 26, we have a waitlist option and can bring on a few more sailors that we can  accommodate based on fleet/rotations and brunch logistics." Racers will compete in Flying Juniors. Registration fees are: skipper/crew teams - $70 and Individuals - $35. More information and the waitlist registration can be found here. The best viewing area is along the waterfront seawall, where there is a beautiful bike/pedestrian path adjacent to DC Sail docks and a small public pier next to the facility. Please click here for a Google Map to dock location. 

Schooner Woodwind
Don't miss the final opportunities for 2022 sailing aboard the Schooner Woodwind.

Schooner Woodwind: Don't miss the final weekend of public sails aboard the beautiful schooner Woodwind. Fall sailing typically offers beautiful autumn breezes, fall foliage, and cooler temperatures. Woodwind and Woodwind II were built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels. The vessels' bars are stocked with wine and beer, including local craft beer.

J/24 ECC 2020
The 2022 J/24 East Coast Championships will unfold this weekend in Annapolis. This shot of sailing during the 2020 event was captured by Will Keyworth.

Championship Racing: The J/24 North Americans and J/22 East Coast Championships hosted by Severn Sailing Association take place October 27-30. It is hoped that fall breezes and sunshine plus cooler air temperatures will combine for excellent racing and spectator viewing. Fall is championship sailing season on the Chesapeake!