Expanding Horizons

Even the most lubberish of stay-at-homes are thrilled when a gallant vessel clears the harbor gracefully and sails out to prove her seaworthiness.

Headmaster Walter Lillard, Tabor Academy’s 1923 Catalog

In an era of post-World War I isolationism, and before the wide availability of commercial air travel, Headmaster Walter H. Lillard had a vision that began in Sippican Harbor and reached toward a faraway horizon. He, along with his successor James W. Wickenden, championed the school’s waterfront location in Tabor’s 1923 Catalog. “[W]hen we see a great ship get under way, there comes the urge to go along as one of the crew and explore the seven seas—to steer by the stars and to gain wisdom through communion with the deep, blue water,” he wrote.

Lillard’s words are accompanied by a photo of a schooner under sail, the crew made up of Tabor students. “They are bound seaward to meet world conditions that other generations have not contended against,” he writes. “It is a new world. Are they prepared for the new conditions?” As a cadet on a ship, Lillard continues later in the same Catalog, a student gains knowledge and discipline that they cannot gain from books. “No slack work is tolerated,” he writes. “Every task on board a ship must be done right.”

Fast forward a century, and much of what Lillard wrote resonates today. The schooner under sail, crewed by a group of Tabor students, is now in its fourth iteration. Today’s SSV Tabor Boy (the fourth school ship and the third named Tabor Boy) is a 115-foot, gaff-rigged, two-masted schooner. She is part sail training vessel, part classroom, and part laboratory. Every fall and spring, Tabor Boy hosts a crew of 22 Seawolves under the direction of a faculty captain, currently Captains Jay Amster and Sara Martin, and a student executive officer. In summers, Tabor Boy hosts orientation trips for incoming students, and she’s even taken students to the Caribbean to conduct coral reef ecology research. In an increasingly complex, interconnected, and often intangible world, Tabor Boy remains true to her original mission: She gives Tabor students the chance to head seaward, to explore, to learn from the stars and deep water, and to find who they are in ways that the classroom cannot teach.

1918 – 1925: Schooner Black Duck Pioneers the Program

In 1918, Alexander Forbes lent Tabor its first sailing vessel, Schooner Black Duck. Forbes was inspired by Lillard’s vision of Tabor as a school that gave its students access to the horizon. Forbes applauded Tabor’s transformation over the summers into “Camp Cleveland,” a camp that offered rudimentary naval and nautical training to boys. Lillard immediately appointed John A. Carlson to captain Black Duck and run the school’s deep-water cruising program.

Black Duck was a 68-foot vessel that could sleep up to 15 people. She was a boon to Tabor and gave the school a means to take students on extended cruises. However, she had no auxiliary engine, which posed a challenge. Joseph J. Smart describes the process of sailing Black Duck through Sippican Harbor in “The School and The Sea: A History of Tabor Academy.” “Her captain,” Smart writes, “recalls the many times when he had to beat to windward to clear the harbor through its narrow, twisted channel; and when he had to lie outside the inner harbor, unable to enter against an ebb tide or for lack of wind.” The 10 boys who crewed Black Duck on her first extended voyage, to New London, Connecticut, “thought it a wonderful way to get home,” Smart writes, and their enthusiasm prompted Lillard to organize more and longer trips.

1925 – 1945: Tabor Acquires the First Tabor Boy

Tabor used Black Duck until 1924. Lillard felt the time had come for Tabor to buy its own sailing ship so that it could always be available to the expanding student body. As nearby New Bedford’s whaling industry was winding to a close, New Bedford native and school trustee Joseph W. Bailey saw an opportunity to continue the maritime spirit at Tabor. Bailey formed a committee that sold “Tabor Boy Bonds” to fund the acquisition of a new ship. After a long search and negotiation on the purchase price, the committee struck gold in 1925: Schooner Robin, located in Camden, Maine, “obviously was the type of ship Tabor Academy could use not only in Buzzards Bay but also in deep water off the entire East Coast,” Smart writes. The ship served the school for 20 years: Renamed Tabor Boy, the auxiliary schooner was one of the largest sailing vessels on the East Coast with an overall length of 88 feet, four inches. She could accommodate 26 people and sported a 66-horsepower engine.

“Tabor Boy could go anywhere with the winds, when available, or with her engine when the tide or the wind was against her,” Smart writes. “With the advent of cruises to ports farther and farther from Marion, it is clear that her arrival in Marion harbor marked the true beginning of Tabor Academy’s distinctive sailing program.” He notes that an uncountable number of Tabor students used the ship, and that she “carr[ied] the school’s name up and down the East Coast … as well as into the very heart of the nation by the long trip up the Hudson River and through the Great Lakes to the Chicago World’s Fair in 1933.”

The school’s sailing program grew through the 1930s. In 1942, wartime restrictions placed boundaries on how often or far Tabor Boy could sail. The ship, built for longer voyages, was aging, in need of costly repairs, and not allowed to sail farther than Martha’s Vineyard, Nantucket, and Cuttyhunk Islands. The school’s flagship vessel needed to adapt to changing times.

1945 – 1954: The Second Tabor Boy Takes on Bermuda

Enter Edlu II, a 68-foot yawl. Captain Carlson himself stood on the deck of Tabor Boy as she was passed by Edlu II in Tabor Boy’s constrained wartime territory. Edlu II was built in 1938, designed for the Newport to Bermuda races. Her owner, Rudolph Schaeffer, had lent her to the United States Coast Guard in 1942 for anti-submarine patrol off the East Coast. In 1945, Headmaster Wickenden announced that Schaeffer had gifted the ship to Tabor.

Edlu II arrived on campus in spring 1946 and was also renamed Tabor Boy. She served the school until 1953 and became a familiar sight up and down the East Coast. “Much more a yacht than her predecessor had been, the yawl yet had enough sail to teach her crews how to harness a force efficiently,” Smart explains. The ship’s speed was enough that Captain Carlson entered her with primarily alumni crews in the prestigious Bermuda Races of 1950 and 1952, carrying the school’s name even farther than had the previous Tabor Boy.

Learning to sail Tabor Boy gives students knowledge that they cannot gain in the classroom, a unique experience that unites generations of Tabor students as they head seaward into the horizon.

1954 – Present: The Third Tabor Boy Grows With the School

After World War II, the size of the Tabor student body increased dramatically. Once again, Tabor needed to reconsider the needs of its program. The school needed a larger vessel to match the larger crew, as well as the students who were eager to take a weekend cruise. The search for a suitable ship began again.

In 1953, Wickenden came across an advertisement for the sale of Schooner Bestevaer, a former Dutch North Sea Pilot Schooner owned by Ralph C. Allen.

A delegation traveled from Tabor to South Carolina to meet Allen and see the schooner. “The ship had lain idle following a rough winter passage from Europe,” Smart writes, and Carlson called her “kind of ornery-looking,” but “sturdy, it was plain to see, and she had every qualification we had been looking for in a ship for boys…”

Bestevaer, the vessel that is today’s Tabor Boy, was built in 1914 — at around the same time Lillard first imagined Tabor’s oceanfront potential. She worked as a pilot schooner off the Netherlands until pilot sailing vessels gave way to pilot steam vessels. In 1926, she found a home in Rotterdam as a sailing scholar ship for men entering the Netherlands Merchant Service. In 1943, Bestevaer was captured by the German Navy. Her whereabouts until 1946 are unknown. By 1950, the Bestevaer was renovated as a cruising yacht for a Dutch company’s executive board. She arrived in Marion on May 20, 1954, ready for the next generation of Tabor’s cruising program.

Thirty-six years after Tabor first used Black Duck to harness the wind in Sippican Harbor en route to New London, the school held a vessel capable of sailing to anywhere in the world. The school had grown along with its sailing program, and Bestevaer was quickly a familiar sight between Maine and Newport, Rhode Island. Captain Carlson held a 38-year career at Tabor and shepherded the program from its nascence to owning Bestevaer, the school’s fourth school ship. Carlson retired in 1955; his replacement, Captain George E. Glaeser, held the Coast Guard-issued Master Mariner unlimited license and began an unparalleled cruising program.

Tabor Boy Expands Programming

Renamed as Tabor Boy in late 1956 (and repainted from white to black), the ship began taking longer cruises on a regular basis: to Bermuda during spring break; to South Carolina over Thanksgiving, where the ship would winter at the home of her previous owner before sailing on to Nassau. In 1971, Tabor Boy even plied the waters off Nova Scotia, Canada. She also attended seemingly every event of maritime significance in New England. She witnessed the arrival of Mayflower II at Plymouth, Massachusetts, in 1957, and the launching of the America’s Cup contender in 1962.

Tabor Boy also entered cultural moments several times. In summer 1956, she hosted the stars of the movie “Moby Dick,” including Gregory Peck, as they met with a troop of Mariner Girls Scouts that had sailed into New Bedford under Captain Carlson. In May 1957, a group of students from Tabor and Emerson College protested President Eisenhower’s budget by re-enacting the Boston Tea Party off the deck of Tabor Boy. The group dumped boxes labeled “Inflation,” “High Spending,” and “Waste” into Boston Harbor. The demonstration kicked off a New England tax rally day promoted by the Greater Boston Chamber of Commerce. In 1976, Tabor Boy participated in Operation Sail, a centerpiece for the American bicentennial.

In 1984, programming shifted to a new “sail training/outward bound” program that opened Tabor Boy to far-flung opportunities for students, parents, alumni, and friends under Captain Glaeser and first mate James Geil. Tabor Boy took on perhaps her most epic voyage when she traversed the Panama Canal in January 1993. Under the command of James Geil, and behind the planning and connections of then-Executive Officer Andrew Major ’93 and his family, Tabor Boy traversed the canal with the assistance of the Pan Canal pilot captain — Nathaniel Gladding ’62, who served as executive officer of Tabor Boy during his own time in Marion. The passage through the Panama Canal marked Tabor Boy’s first taste of the Pacific Ocean. The voyage also included a partnership with scientists at the Smithsonian Tropical Research Institute, who lectured students on relevant topics and allowed them access to their labs.

In 2019, Tabor Boy received another honor: She was invited to the Marion Bermuda race to challenge Spirit of Bermuda, which had previously raced uncontested in her class. Then-Executive Officer Chip Connard ’19 recalled the chairman of the Bermuda Sloop Foundation, throwing “down the gauntlet.”

“This was followed with some good-natured banter including a generous offer to give us a two-day handicap,” Connard continues. “We accepted the challenge and countered by wishing the Spirit of Bermuda crew good luck in beating a bunch of high school kids!” The bunch of high school kids prevailed, and Tabor Boy won the Classic Yacht division.

Tabor Boy has grown and changed with the school. Today’s SSV Tabor Boy remains a vital part of Tabor’s identity. But, Headmaster Lillard’s words from the 1923 Catalog remain true: Learning to sail Tabor Boy gives students knowledge that they cannot gain in the classroom, a unique experience that unites generations of Tabor students as they head seaward into the horizon.