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In 1939, the MATTIE'S charm attracted the attention of Captain Frank Swift of Camden, whose love of sailing and entrepreneurial spirit had guided him in the launch of the first windjammer passenger tour just a few years before. After chartering the MATTIE from Captain Shepard for two seasons, he purchased the vessel in 1940 and began her career as a passenger schooner.

Shepard, a close friend of Swift, stayed on as captain of the MATTIE for several years, becoming one of the most popular skippers in Swift's fleet. At the end of World War II, Swift added the 71-foot schooner Mercantile to the Maine Windjammer Cruises ® fleet along with the MATTIE, to his growing list of vessels. Swift's other vessels were the LYDIA M .WEBSTER, ANNIE F. KIMBALL, CLINTON, and LOIS M. CANDAGE. Together, they made up Maine Windjammer Cruises®.

​Swift's business struggled through the early years, but the popularity of his sailing tours grew as passengers spread the word of their experiences. Camden's reputation as a destination grew as well, and tours aboard the town's growing fleet of windjammers became one of its most exciting attractions.

[with additions to present] MASTERS 1937-1940 William F. Shepard, Deer Isle, ME
1941-1942 Parker J. Hall
1942-1954 Manley S. Grant, Stockton Springs, ME
1955-1956 Fremont J. Colton
1957-1960 Frank Swift, Camden, ME
1957-1960 Wynes Haskell, Deer Isle, ME
1957-1960 Montaford Haskell, Deer Isle, ME
1957-1960 Walter T. Hutchinson, Deer Isle, ME
1957-1960 Williamson E. Johnson
1961-1961 Jim Nisbet, Camden, ME
1962-1970 Fred C. Morey, Deer Isle, ME
1969-1969 Fred Johnson, Bailey Island, ME
1970-1970 Leslie E. Bex Jr., Camden, ME
1971-1974 Michael Anderson, Camden, ME
1975-1976 Paul DeOrsay, Camden, ME
1977-1988 Theodore C Schmidt, Camden, ME
1989-1990 Restoration
1990— 2022 Ray Williamson, Camden, ME


1882-1906 Edwin Bailey: 1/8 Patchogue, NY
1882-1897 Seymour Ketcham: 1/8, 7/32 Patchogue, NY
1882-1919 John S Havens 1/16 Patchogue, NY
1882-1919 Nathaniel O Swetzey 1/16 Patchogue NY
1882-1894 Sidney Newoton 1/16 Patchogue NY
1882-1889 Archie Mills 1/32 Patchogue NY
1882-1907 Joseph S Howell 1/32 York River VA & Patchogue
1882-1894 Edgar Gilette 1/16 Bayport NY
1882-1907 William C Rogers 1/16 Bayport NY
1882-1890 Charles Z Howell 1/16 NYC & Patchogue NY
1882-1888 Josiah H Still 1/8 New York City
1882-1892 Joseph Mongey 1/16 New York City
1882-1900 Francis T Baker 1/16 New York City
1888-1897 John Decker 1/8 York River VA
1889-1892 Robert Mills 1/32 Patchogue NY
1890-1902 James Bell 1/16 Brooklyn NY
1894-1907 William A Arnold 1/16 Bayport NY
1894-1897 Messerau S Minor 1/32 Staten Island NY
1894-1897 George T Jones 1/32 Staten Island NY
1897-1919 Charles F Terry 13/32 to 11/16 Sayville NY
1906-1919 Martha B Bailey 1/8 Patchogue NY
1907-1919 Ambrose G Gillette 1/16 Bayport NY
1915-1919 Floyd G Terry 1/32 New Haven, CT
1919-1919 Louise B Terry 1/8 Sayville NY
1919-1937 Herbert L Black, South Brooksville ME
1937-1940 William F Shepard, Deer Isle, ME
1940-1961 Frank Swift, Camden, ME
1961-1969 Jim Nisbet, Camden, ME
1969-1985 Leslie E Bex, Jr., Camden, ME
1985-2022 Ray & Ann Williamson, Camden, ME



REGISTERED DIMENSIONS 1882-1906 Length: 72 feet Breadth: 23.5 feet Depth: 6 feet Gross Tonnage: 68.13 Net Tonnage: 64.73 (to 1899) Net Tonnage: 58.79 (1899-1906) SIM'S LIST OF MASTERS 1882-1937 1882-1897 Seymour Ketcham, Patchogue, NY
1897-1919 Charles F. Terry, Sayville, NY
1920-1937 Herbert L. Black, S Brooksville, ME
1920-1937 Guy Black, S Brooksville, ME

[Originally Researched and written by J.W. Sims in 1977 with added content by Capt. Ray and David Munson. Combined into a single, chronological narrative by Q. Donleavy ]

Upon completion of the rebuild, he had Martha rechristen the boat with her nickname - Mattie. 

Some indication of her range can be ascertained from the fact that enrollment and registry documents were issued to her during this period at Patchogue, Fall River, New Haven, Providence, New York City, Baltimore, and Norfolk.

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.

The Mattie's early deck plan included two cargo hatches between the masts and one between the mainmast and the after deckhouse. The main topmast was removed when the Mattie became a cruise schooner.


From January 1915 until March 1919 the MATTIE'S homeport was New Haven, Connecticut. During this period she was in the coasting trade, most likely sailing on Long Island Sound, carrying oysters and oyster shells, likely potatoes to New York City, and sand from the quarries along the north shore of Long Island. After this service, her homeport was again Patchogue until the end of 1919.

"She was one of the finest vessels in the cargo trade."

George Miller, a local sailmaker at the time, probably made the original sails. The carpenter's certificate for the GRACE BAILEY is dated 21 November 1882, and her first certificate of enrollment in the coasting trade was issued on November 23 that same year. No waiting around!

The vessel was originally named after Edwin Bailey's daughter Grace Bailey (Dowd), born in April 1882.


From launch through 1914, the vessel was engaged in the coasting and foreign trades, with several voyages to the West Indies. Her homeports were the Great South Bay towns of Patchogue and Sayville. Initially Captained by Seymour Ketcham, much of her work included carrying lumber from South Carolina to Georgia.

During these early years, the MATTIE'S rig included fore and main topmasts and topsails, jib-boom, and flying jib. With the advent of the gasoline-powered yawl boat and hoisting engine, it became possible to reduce the size of the crew. This, in turn, brought about a light weather sail.


Though Bailey 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, Martha (Mattie) born 1888, Upon completion of the rebuild in, he had Martha rechristen the boat with her nickname - Mattie. 


Edwin Bailey also gave his granddaughter his one-eighth share in the vessel. In 1919 Martha Bailey reluctantly sold her share when Captain Herbert L. Black, of Brooksville, Maine, purchased the Mattie and brought her back to Maine to replace his schooner Oakwoods.


In November 1919, Black's schooner, Oakwoods, was accidentally rammed and sunk by the American submarine R-3 in Buzzards Bay near the Cape Cod Canal. 

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GRACE BAILEY heads out to sea. The Grace Bailey sailed under the name Mattie for more than 80 years. (Image courtesy of Penobscot Marine Museum)

Captain Black received a payment from the government for his loss of the Oakwoods, and years later, after his death, it was discovered that the check had never been cashed. A search revealed the check hidden over a beam in the Mattie's master cabin.

During her time with Captain Black, and later with Captain William Shepard, the MATTIE sailed as a bay coaster in Maine waters, carrying general cargo, pulpwood to Bucksport and Brewer, and perhaps coal to Maine islands. She also went farther from home, carrying boxwood from Ellsworth to Lynn, Massachusetts, salt cod from Maine ports to Gloucester, and hardwood to Boston.

Twenty years of hauling general cargo up and down the coast proved the MATTIE to be a strong and dependable schooner in Maine waters, and her graceful lines and easy manner made her a popular boat with all who sailed her.

In 1939, the MATTIE'S charm attracted the attention of Captain Frank Swift of Camden.

MATTIE 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.

Then 104 years old, 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.

She has served longer and carried more passengers than any other windjammer.

The GRACE BAILEY represents some of Oliver Perry Smith's finest work. 

The GRACE BAILEY represents some of Oliver Perry Smith's finest work. The care that he took in crafting the vessel shines through even today. GRACE BAILEY  was crafted from the finest materials available, and the installation of every plank and beam was overseen by Smith himself. 


Inspired by friendship and guided by a desire to make the shared enterprise between him and Edwin Bailey a success, Smith poured every ounce of his skill and experience into the creation of GRACE BAILEY. His dedication and attention to detail on the project may well be the reason the ship survived while so many of the coasters faded into history.

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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.

Vintage Grace Bailey passenger pic.jpg

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.


Grace Bailey


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Schooner GRACE BAILEY was built in Patchogue, New York, 1882 by Oliver Perry Smith at his boatyard on the Patchogue River, in Patchogue, New York.

Despite the broad range of his boat-building abilities, Smith's true specialty was coastal schooners, and he had a reputation for crafting vessels that were both precisely maneuverable and exceptionally quick. His boats often set the standard for speed between ports, with his R.H. Vermilyea making the run from Cuba to New York in only six days.

Smith's carpenters completed the Grace Bailey on November 22, 1882, and she began her career in the coasting trade two days later.

Captain Seymour Ketcham piloted the vessel during its first 15 years of service, making frequent runs up and down the East Coast as well as several voyages to the West Indies. In 1897, Charles Terry took over as captain when Ketcham gave up his position as master and part-owner of the boat.

Oliver Perry smith.jpg

Famed Long Island boat builder Oliver Perry Smith poured every ounce of his skill and experience into the creation of GRACE BAILEY

She was originally constructed to serve the needs of the E. Bailey and Sons Lumber Company by carrying lumber from southern ports to Patchogue. Because of Edwin Bailey's high standards and his access to fine wood, only the best was used in the construction of the GRACE BAILEY Smith's boatyard was located across the river from the lumber mill.


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.

Completed November 22, 1882, she began her career in the coasting trade two days later.

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