A Bit of Schooner Sailing Magic

It was a very slow start to the GCBSR October 13. Photo by Cindy Wallach

Great Chesapeake Bay Schooner Race

When I wanted to write something about the Great Chesapeake Bay Schooner Race (GCBSR), I found myself asking, ‘Self, what do you think people who have not been a part of this sailing adventure would like to hear?

The use of the word “adventure” is not accidental. Adventure is the name of our schooner. We purchased her in 2009, and she has also been our home for the last two years. This year was our eighth start in the GCBSR, and every year has been a new story to share. Our roots with the race go back further. The first race that we shared with Captain Dan MacLeod of Schooner Sally B (the 2016 winner) was in the aftermath of 9/11. There were questions of whether or not the race would even be held that year, but in the spirit of the schooner family, it was determined that absolutely, the race should go. Many times in the years that have passed since, I have found myself thinking that it is just this spirit, and this faith, and this love of these boats that are so tied to our history that makes this race, and the people who sail it, just what it is. I did not sail that year, but Dick did, and thus began our history with the schooners.

Schooners come in many different shapes and sizes, as do all sailing vessels. They tend to handle far differently from sloops, which Dick and I had always sailed previously. Over the years of sailing on Sally B, we began to learn how to sail the boats and to meet and know all of the people who make this family so very special. I was support crew for many years, and then was finally able to get the time off work in 2007 and 2008 to do the race myself on my beloved schooner of another captain, Sally B. Another schooner came into the dock in Portsmouth in that October of 2008 with a sign attached to the lifeline…”Reluctantly For Sale.” The name of that schooner was Adventure. The rest is history. 

Photo of Schooner Light Reign by Mark Duehmig
Schooner sailors sailing 130 miles down the Chesapeake to raise funds for local charities.

Getting ready for the race each year is always a time of high highs and those other moments as you make sure that your vessel is ready for this trip down the Bay. Class A and AA finish at Thimble Shoals Light at the mouth of the James River in Virginia. Class B and C finish at Windmill Point Light, south of the Potomac River. It is 120 nautical miles to Thimble; 80 to Windmill. Even if you finish at Windmill, you still have to get into Portsmouth if you want to go to the party. And of course you want to go to the party. 

We have done this race where the conditions have been amazing: full moon, wind off the starboard quarter, reasonable seas (even at the mouth of the Potomac), breeze fresh but manageable. Yes, that happened, once. When that doesn’t happen, it can be similar to this year. We started the race anchored. No wind, but plenty of current. Then, it graduated throughout the night to gusts of 30 plus and seas from four to six feet and probably some bigger than that. We broke our foresail gaff. Lady Maryland finished with a broken boom, as did A.J. Meerwald. Adventurer lost her main halyard. But we all made it to the party. And thanks to networking, the talking kind, not the internet kind, repairs to the breaks were and will be made, and that brings us back to the magic.

When I was growing up, thanks to my dad, I was part of the Alberg 30 Association. That connection is still a part of my life. Now Dick and I and all our family have been so very, very lucky to have been gathered into the schooner family. I find myself struggling with how to phrase how much it means to all of us. There have been times on the GCBSR where we have had all three of our children onboard as crew, along with friends who don’t seem to mind when it is cold, and wet, and really windy. The family continues to grow. 

Leigh and Dick Woodling's Adventure placed first in Class A at the Great Chesapeake Bay Schooner Race

I think I will wrap it up with a quote from my son-in-law, Taylor. We were sitting in the cockpit after the finish this year. We had reefed the main, fired up the engine, and pretty much everyone else was sleeping. This is the second year in a row that Taylor has come along with us in what could be termed as less-than-favorable conditions. I looked at him, with the good ole Chesapeake Bay boiling along in the background, and said “Taylor, I just love that you will come and do this with us.” Taylor’s response. “I’ve always been into extreme sports.” And so it is with sailing schooners on the Bay.

If you have a schooner, if you have ever wanted to know more about schooners, there is much out there. We are always looking for volunteers who may be interested not just in helping out with the GCBSR itself, but in furthering the many ways that we all can help our Bay, our kids, our heritage. Please feel free to contact me at [email protected] with questions, stories, or comments, or a place to meet for happy hour.
~by Leigh Woodling

GCBSR website: gcbsr.org; American Schooner Association: amschooner.net