In the Greg Pease photo collection you will see a few photos of Lady Maryland leading the Great Chesapeake Bay Schooner Race...along with some of Pride of Baltimore and Virginia (fastest schooner of the bay).
Ron, that was Lane Brigg's "tugantine" Norfolk Rebel. Capt. Briggs was the ramrod for this race until he passed on a few years ago, but I understand his boy now skippers Rebel .
October can bring some really fresh breezes to the Bay and when it does these big historic work boats with abundant and balanced sail plans, long waterlines and beamy hulls can really move. Even the power boats can't keep up with a heavy schooner in those conditions. The upper Chesapeake has a rich history of go-fast sailboats, Baltimore Clippers and Eastern Shore Pungys for distance trade, or the lovely Bugeyes and Skipjacks of the fishing and local trade. Much of the early designs like the Bugeye were based on native-american boat construction methods- shaped logs pinned together. Here is a shot of the Edna Lockwood, a 125 y/o Bugeye built on Tilghman Island by the Harrison family, currently in the Chesapeake Bay Maritime Museum at St. Michaels for a rebuild.