1990 - Updated History of the Grace Bailey

The Grace Bailey During the mid 1800s a particular friendship and business relationship developed between two men on opposite sides of the Patchogue River in Patchogue, Long Island, New York. Oliver Perry Smith, the leading local shipbuilder relied on his neighbor Edwin Bailey of Bailey Lumber Mills to provide materials for his vessels. Likewise, Mr. Bailey relied on Mr. Smith for vessels with which to transport the lumber to his mills.




Due to his high standard for excellence and his access to the finest of woods, Mr. Bailey commissioned in 1882 a very special vessel. That vessel launched Nov. 21 was named after his newborn daughter, Grace Bailey, born in April that same year.

She was immediately put into service carrying hard pine from the Carolinas and Georgia to his mills in Patchogue. During her early years she also registered for foreign commerce making voyages to the West Indies in the fruit trade.

Though he was the principal owner, as was common, he had other shareholders in the vessel including the captain, Seymour Ketcham. In 1906 they undertook a major refit of the vessel, and at that time Mr. Bailey gave one-eighth share to his favorite Granddaughter, Mattie. At that time he also rechristened the boat with her name.

During the early years of the 20th century she carried general cargo in the New York area and around the Long Island Sound. In 1919 she was sold to Capt. Herbert Black of Brookville, Maine to replace his schooner Oakwoods, which was rammed and sunk by a U.S. submarine. Capt. Black was paid for his lost vessel with a government check that he apparently never cashed, as it was found, hidden behind a beam in the Captains cabin aboard the Mattie many years later.





According to John F. Leavitt in his book "Wake of the Coasters," she was one of the finest vessels in the cargo trade. Capt. Black sailed her throughout New England with a variety of cargoes including granite to build the New York Post Office and Grand Central Station.

With the end of the era of cargo under sail rapidly approaching, Capt. Frank Swift chartered her in 1939 to add to his growing fleet: Maine Windjammer Cruises®. He purchased the vessel outright in 1940, and she quickly became the favorite among passengers and crew alike. Capt. Swift took her as his flagship and sailed her for many years. The Mattie took a brief hiatus from her windjammer career in 1942 when she performed her war service as the first training vessel for the new Maine Maritime Academy.

Mattie returned to the windjammer business, and she outlasted all of the earlier vessels in the fleet. She has served longer and carried more passengers than any other windjammer. The success of this vessel can be directly attributed to the unique friendship and collaboration of Edwin Bailey and Oliver Perry Smith in 1882.




The Grace Bailey rejoined the fleet of Maine Windjammer Cruises® after more than 20,000 hours of restoration. (Photo by Linda K. Serafin)


One hundred years later Ray Williamson, also from Long Island, signed aboard as a deckhand. After seven years in the Virgin Islands as a charter boat captain, the lure of Maine?s famous windjammers brought him to Camden. Accepting this entry level position as the only one available, he learned the ropes. During the next three years he served as captain for Maine Windjammer Cruises® under the ownership of Capt. Les Bex, and in 1986, Capt. Ray and Ann Williamson purchased the fleet.




The Grace Bailey as she appears today.


Then 104 years old, the Mattie (Grace Bailey) was in need of serious repairs. The Williamsons committed to the preservation of the vessel and undertook a complete restoration effort. The project, which took over a year, was the topic for an article in Historic Preservation magazine.

Read more in the June 2005 MWC Enewsletter