STBSP Ep, 113, The Great Chesapeake Bay Schooner Race with Paul Carroll and Jennifer Kaye of The Woodwinds!

by JeffreyWettig | September 12th, 2019

The Great Chesapeake Bay Schooner Race 2019

Greetings folks! Welcome to episode 113 of The Shooting The Breeze Sailing Podcast (STBSP) from The Escape Pods Dot Com. This time around we are speaking with Paul Carroll and Jennifer Kaye about The Great Chesapeake Bay Schooner Race, which happens in Mid-October every year, and features 25 to 40 Schooners of all shapes and sizes, old and new, racing each other from the Bay Bridge to Norfolk. Both Paul and Jennifer participate in the racing, he for the last 15 or so years on his fathers boat, and her for the past 23 years aboard her family’s charter schooner Woodwind 1. The Great Chesapeake Bay Schooner Race is a non-profit organization that puts on the race, organizes education opportunities during the pre and post race activities, hosts the Parade of Sail in Baltimore’s Inner Harbor the evening before the race, and donates proceeds from entry fees, donations, and Sponsorships to various Bay related charities and organizations. It is literally Racing to Save the Bay and this year is the 30th annual edition of the race. Like all races, it began with two boats, The Pride of Baltimore 2 vs. The Norfolk Rebel racing from North to South for bragging rights, and today there are all sorts of Schooners entered in the race, from small family boats, to large 100ft plus tall ships run by non-profit organizations. This year even features a new Trophy for the winner of the race between 2 Sheerwater 45’s named Moonbeam and Apella. There is an awards ceremony in Norfolk for the participants as well as the ability to check out the boats by the public. There are also Volunteer positions and Sponsorship opportunities available.
There are many places you can find out more, head on over to the website
You can also find them on Facebook at
Jennifer Kaye and her family run the day charter schooners Woodwind and Woodwind 2 in Annapolis, MD.
Listen in at the end for a special impromptu rendition of Chuck Berry’s “No particular place to go,” as performed on the porch at HPYC by Josh Taylor of the Hot Club of Reading, Mike Nikolidakis, and Robert Williams.
You can download Episode 113 of The Shooting The Breeze Sailing Podcast Here
Find it on Itunes or Google Play,
Or stream it below,

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Intro Music by yours truly and Greg Young, available via The Incoherents. The Lean Years Volume 2, on Itunes.
Break music, “Wild Winds of Misfortune” by Leo Disanto of The Vinegar Creek Constituency, and “The Wild Rover” as performed by The Ogham Stones
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