Date: October 18, 2025
The Great Chesapeake Bay Schooner Race. Unlike the past several races, breeze was favorable out of the North, and of decent strength! Following the festivities in Baltimore, Pride of Baltimore II motored down to the start line just off Annapolis early Thursday Morning. Getting into the area about an hour ahead of the start we set the main, staysail, and jib and began to prep other sail. The start line consisted of a committee boat, pin end and a reaching mark. Making the start a port tack to the east before being able to bear away and head towards Norfolk. With a bit of maneuvering, we were able to get in position to be the second across the line, shortly after schooner Woodwind and a few boat lengths in front of schooner Virginia. Setting the fore just before the start and the fore topsail as we were crossing the line. Bearing away at the reaching mark, sheeting everything out, we then were able to get the jib top up before our first gybe close Kent Island over on the Eastern Shore.
After the gybe, we were able to get the topgallant, studding sail, and main gaff topsail on, settling in to a comfortable 8 knots of boat speed. With the wind holding steady, we were able to sneak past Poplar Island and make our way over toward the Western Shore, gybing for the second time around 1530. Sheet in the loose-footed fore and aft sails, stun’sl down, brace the yards and haul in the main for a controlled gybe. Running backstays and other gear getting appropriately tensioned and struck throughout that process. After the gybe, the stun’sl goes back up on the new tack and away we go!
We were able to keep speeds between 8–10.5 knots, gybing again across the bay from Point No Point, another in the mouth of the Potomac to lay a good line for clearing Smith Point around 2100 and heading over towards the Eastern Shore for some cleaner and fresher air. After running out of usable sea room, we gybed around 2300. By this point, the breeze had freshened and Pride of Baltimore II was making 10–11 knots with a few 12s from time to time. We had also taken in the stun’sl by this point due to some gear failure and the main gaff topsail to ease the burden on the helm a bit. This brought us down to the mouth of the York River where as expected, the wind began to get lighter the closer to shore we got.
Now you may be thinking to yourself at this point, what about the other boats? What have they been doing? Where are schooner Virginia and Woodwind? Well, through the entire race, Virginia and Pride of Baltimore II played a game of “I am the leader now.” With Virginia’s ability to point deeper than Pride of Baltimore II and maintain speed, she took an early lead. We were able to eat some of that time up once our stun’sl came into play and snuck ahead for a bit. Virginia once again was able to get ahead of Pride of Baltimore II with some very good deep downwind sailing over by the Eastern Shore while we were sailing toward the Potomac. Pride of Baltimore II was once again able to catch up and get ahead after we were south of Smith Point. Virginia, unfortunately, falling into a bit of a no-wind hole on the Western Shore, while Pride of Baltimore II found increased fresh steady breeze on the Eastern Shore. Schooner Woodwind took an early lead over both boats and was able to maintain that lead until Smith Point when Virginia was able to overtake her. Pride of Baltimore II is finally able to gain enough ground to overtake her and Virginia at Windmill Point. At which point I lost track of Woodwind in the dark and many lights of the southern bay, as without AIS she can be hard to spot sometimes. But, back to the mouth of the York River. There we were, slowing down, barely making Thimble Shoal Light. Here comes Virginia. Her starboard green running light getting brighter and brighter. Her speeds according to AIS in the 10 and 11s laying a good line to Thimble Shoal Light (the finish). Ours in the 8–9s. Time to gybe, get that cleaner air! At 0200 we gybed around, not soon after we were back up to speeds in the 10–11 range and maintaining our lead over Virginia. One more gybe at 0220 we made our way to the finish line, crossing at 0254. About 6 boat lengths in front of Virginia. From a start where we were a few boat lengths in front of schooner Virginia, to a finish where we were a few boat length in front, seems like a close race to me!
It wasn’t until we were in the river headed in to Norfolk that I was able to check the tracking app and find out we had also crossed in front of Woodwind, claiming line honors for Pride of Baltimore II!
My sincerest compliments to the crew, executing 7 gybes with full sail set in 20 knots and upwards of breeze is no small feat. To do so enthusiastically, and with good cheer even at 0200 in the morning, speaks highly of their character and professionalism.
As far as race results go, in our class on corrected time, schooner Virginia placed first, Lady Maryland took second with Pride of Baltimore II claimed third.
My thanks to all who watched from the sidelines as well, y’all were the best cheering squad!
Signed,
Capt. Jeff Crosb
