Built in the 1880s, this attractive hotel inspired tourists to visit the Outer Cape

Pier pressure? Guests donned their Sunday best when visiting the Chequesset Inn, which was built in 1886. In this photo, one can see men, women and children wearing hats and—in the background—the water tower that kept things running smoothly. Photo courtesy of the Wellfleet Historical Society

With the opening of the Chequesset Inn in 1886, Captain Lorenzo Dow Baker, a.k.a. “The Banana King,” thrust the town of Wellfleet into the new leisure pastime that began in The Gilded Age of wealth and prosperity. Intrigued by the resorts he saw in Florida and Jamaica, Baker resolved to bring the world to the rustic beauty of his native town.

Wellfleet’s first, and only, “Grand Hotel” was advertised as the “Hotel Over The Sea.” Built on the old Mercantile Wharf, the inn extended 400 feet into Wellfleet Harbor. The four-floor hotel was designed to resemble an ocean liner with 62 guest rooms reminiscent of ship’s cabins. Ironically, it wasn’t ships that brought guests to the inn; it was the railroad, which reached Wellfleet in the 1870s, providing fast, convenient access to the remote Outer Cape community.

The Chequesset Inn was more than a hotel; it was an all-inclusive resort. A brochure for the inn touted “sea and lake fishing, boating, tennis, billiards, bowling and orchestra.” Skiffs tied to a float alongside the pier were available for guests to row. The powered launch, Osprey, could be chartered for deep sea fishing or picnic clambakes on Great Island or Billingsgate. On shore, Mayo Beach provided a calm, Cape Cod Bay bathing beach for families. There were bathhouses and changing rooms, a tennis court, a bowling alley, and a stucco garage that housed carriages, and later automobiles, that transported guests to Wellfleet’s inland fresh water ponds. Fresh water was gravity-fed to the inn from a water tower on the sand bluff directly behind the hotel. A viewing platform stood atop the tower, providing scenic vistas of Wellfleet Harbor and shorelines extending to the Upper Cape. Visiting guests signed up for the “American Plan,” a package that provided three meals per day as well as access to all the inn’s amenities.

In his 1974 book I Remember Cape Cod, author E. C. Janes recalls his boyhood summer vacations in Wellfleet starting in 1913. He writes that the “orchestra” mentioned in the inn’s brochure was a trio that provided background music during meals, and musical performances were provided on “amateur nights,” when guests and staff performed to the delight of the audience. “The price in 1916 came to $15 a week per person on the American Plan …,” Janes writes. “As everyone knew … a whole family could live for two weeks or more on less than $15. It was clear … that to stay at the Chequesset Inn you had to be rich.”

Janes recalls the gas generator that produced electricity was shut down nightly at 10:30 p.m. in keeping with Baker’s Methodist views of economy and propriety. After that, the only lighting to be found was in the spacious bathrooms. So, it was in the bathrooms that male guests conducted secretive, late night poker games.

Photo courtesy of the Wellfleet Historical Society

Just west of the hotel on Chequesset Bluff, spacious summer cottages were built to accommodate larger families. In 1933, Edward Hopper, the renowned artist, painted them in his watercolor “Cottages at Wellfleet,” which propelled them to artistic immortality.

Captain Lorenzo Dow Baker (1840-1908) was the founder of what became United Fruit Company, known as Chiquita Banana. Born in the Wellfleet village of Bound Brook, Baker went to sea as a cabin boy at the age of 10, was a captain by 20, and soon after owned his own ship. In 1870, Baker’s Telegraph delivered a cargo of mining equipment to Venezuela.

Admont Gulick Clark, Captain United States Coast Guard, retired, describes the journey in his 2000 book, Sea Stories of Old Cape Cod and the Islands. On the return trip, the empty ship was damaged by a storm and limped into Port Morant, Jamaica. Merchants were reluctant to provide goods for his repaired craft, but eventually he filled the empty hold with coconuts and green bananas. Running his bilge pumps all the way to New York, Baker sold the remaining, unspoiled bananas that had cost him 25 cents per bunch for $3 per bunch, thus beginning the lucrative trade that would establish his fortune.

Baker partnered with Jesse Freeman, his Wellfleet boyhood friend, and together they dominated the tropical fruit industry for decades. Based in Boston, Freeman handled marketing and distribution, while Baker, his Wellfleet wife, Martha (Hopkins), and four children (Loren, Joshua, Martha Alberta and Reuben), moved to Jamaica, where he expanded fruit production. The sugar cane industry had collapsed following the British Empire’s abolishment of slavery, and Jamaicans were eager for a new cash crop.  Baker purchased many of the decaying sugar plantations and converted them to grow bananas.

David Wright, staff member of the Wellfleet Historical Society and author of The Famous Beds of Wellfleet: A Shellfishing History, says the impact Baker had on the community can still be observed today. “Baker and the inn contributed to the two things Wellfleet is known for now: shellfishing and the hospitality industry.” In 1902, Baker built the first gas-powered trawler, The Cultivator, and Mercantile Wharf became home to the Massachusetts Department of Fisheries Shellfish Laboratory and Quahog Hatchery. Starting in 1905, using the shellfish laboratory as his base, Dr. David Belding conducted a research study on the shellfish beds of Wellfleet Harbor. A present-day shellfish grant holder, Mike Parlante, Jr., states that Dr. Belding’s research is still used today by the thriving aquaculture industry.

Built on Mercantile Wharf, which stretched out into Wellfleet Harbor, The Chequesset Inn was designed to look something like a ship. In this north-facing depiction, Mayo Beach is to the right. Photo courtesy of the Wellfleet Historical Society

Baker was named after a Methodist preacher, and he remained a devout Methodist and non-drinker throughout his life. He installed a pipe organ onboard Telegraph and hymns were played at meals and Sunday services. A resident of Wellfleet, Jeff Tash teaches a course on Wellfleet history for the town’s Open University, and lives in a newer house at Chequessett Bluff. Tash says Baker’s personal teetotaling philosophy also extended to the inn. “No liquor was allowed at the inn,” says Tash, “and this may have limited the inn’s clientele in its competition with other Cape resorts, such as the Chatham Bars Inn,” which was founded in 1914.

Baker’s family lived in Jamaica, but spent summers in Wellfleet. Baker built an estate, Belvernon, on several acres of land behind Wellfleet’s town center. Jean Baker is his surviving granddaughter by her marriage to Captain Reuben Baker, Jr. In an interview for this article, she shared her memories of the property. “Belvernon—meaning beautiful green lawns—was a combination of three houses put together, a total of 32 rooms,” she says. Among Baker’s properties in Jamaica was a resort hotel, the Titchfield. “When Grandfather closed [the hotel] in Jamaica, during the hot summer months, he brought the hotel staff here for the season,” Jean Baker says. The family estate had its own bowling alleys, tennis and croquet courts, and extensive lawns and gardens. Bunches of bananas hung on the porch and guests were encouraged to help themselves. Today, most of the estate land has been sold, and the Baker family no longer owns the home. The original house, however, still exists on Baker Lane behind Wellfleet’s town center.

Baker’s eldest son, Loren, built his own summer home on Chequessett Bluff. Its unique design was based on a house Loren had seen in his travels. Unlike anything on Cape Cod, the curved, sloping roof and domed turret gave it the nickname, “The Elephant House,” most likely due to its appearance from the sea. The home is on the western edge of Baker’s original Chequessett Cottages off of Chequesset Neck Road.

In 1908 Captain Baker developed a serious lung infection and left Jamaica to receive medical treatment in Boston. Soon after his arrival, he died at the Parker House at the age of 68. By then, United Fruit Company had been incorporated and Baker’s role had been reduced to a mere figurehead. However, the family continued his other enterprises, including the Chequesset Inn.

In 1934 New England suffered a brutally cold winter that froze much of Wellfleet Harbor. When a major blizzard struck the Cape, ice floes battered the pilings of the aging Mercantile Wharf. The pier shifted, the hotel buckled, and portions of the inn collapsed. In the midst of the nation’s Great Depression, rebuilding the pier and hotel was deemed out of the question, and so Wellfleet’s “Grand Hotel” era came to an end. Today, all that remains of the Chequesset Inn are the rotting stubs of pier pilings that only appear at low tide, and a plaque on a boulder at the corner of Kendrick Avenue that honors Captain Baker—and the hotel that started Wellfleet’s tourist trade.