The Castles, and Mysteries, of the Thousand Islands

When you first see the cedar-shingled T-shirt shops and smell the diner-fried eggs of Alexandria Bay, New York, you might have trouble picturing the down-to-earth town as a millionaires’ haven. But look across the St. Lawrence River and you’ll see a castle, and then you might start to understand this place has a storied past. Still, it will take some time to appreciate the grandeur of an earlier century—and the mysteries behind today's casual summer village.

The first surprise for many might be that the Thousand Islands is an actual place. These days, it’s perhaps more famous as a tart salad dressing—but it’s also a real group of 1864 islands on the watery border between New York and Canada. The area basked in 30 years of glory as the summer colony for America’s wealthiest Gilded Age industrialists, and even President Ulysses Grant vacationed there. The story goes that The New York Times stationed a Thousand Islands correspondent there to report on high society’s doings

The millionaires bought their own private islands and built castles that remain today—along with questions. Take a cruise with a local charter, like Uncle Sam’s Boat Tours, and you can consider them up close.

Singer Castle

Exactly how creepy is Singer Castle?

This European-inspired castle rose up on Dark Island as a hunting retreat for Frederick Bourne, the president of the Singer sewing machine company. He seemed to build it ready for his ghost to one day haunt. The stone walls feel medieval. Turrets, armor, and secret passageways are tucked all over.

How eerie does it feel? You can hop off your boat cruise and tour it during the day, but that won’t fully reveal the answer. The brave, curious, and deep-pocketed can rent it for the night (at rates around $700) to find out.

Boldt Castle

Why wasn’t Boldt Castle finished? The president of the Waldorf-Astoria Hotel commissioned this 120-room showplace for Heart Island. The official story is that he planned to give the over-the-top summer home to his wife, Louise, on Valentine’s Day. That January, she died of “apparent heart failure” at 42. Construction stopped—and never resumed. Boldt was heartbroken—or was he? Some whisper to this day that Louise died of a drug overdose, or ran off with the chauffeur.

For nearly 75 years, the castle sat unfinished. Then the Thousand Islands Bridge Authority began a slow renovation. They're said to be around $38 million in. Entire floors are left to restore. But the ballroom, dining room, library, and several bedrooms have been recreated. Regardless of the real heartbreak behind it, Boldt Castle now inspires modern-day romance, hosting some 150 weddings per year.

Where did they stash all that liquor? During Prohibition, rumrunners used to skim across the watery international border in the St. Lawrence River smuggling liquor from Canada to the U.S., with legend saying they would hide whatever they were carrying to reclaim later when law enforcement got too close. But the border is so jagged, it’s hard to know which side your boat is on at any given moment. The owner of Zavikon Island, for instance, built a 32-foot bridge to the islet he also owned behind it. Saying Zavikon is in Canada and the little island is in the U.S., he called it the world’s shortest international bridge. But even that’s in dispute—some say it’s a tourism ploy, and that both islands are Canadian.

With a border so questionable—and tens of thousands of possible hiding spots–where did the bootleggers tuck their stashes? Unfortunately, those answers may have died with them.

A circa 1903 postcard depicting Calumet Castle. Image Credit: New York Public Library // Public Domain

 
What happened to Calumet Castle? An elegant water-tower-turned-lighthouse is all that stands of a third castle. Calumet was actually the first of the Thousand Islands’ castles, built by tobacco tycoon and hotelier Charles Emery in 1894. Like Boldt, Calumet has a tragic story of loss. Emery’s luxury Thousand Islands hotel, the New Hotel Frontenac, burned down in a fire that started (ironically for a man who made his fortune in cigarettes) with a musician smoking in his room. Emery’s first wife died young, and his second wife, Irene, died in Calumet Castle on his birthday in 1907. After that he shut the castle—which had hosted lavish parties with 10,000 Japanese lanterns illuminating the St. Lawrence River—for good.

Four decades later, in 1956, the massive stone building burned down. Was it arson? Did the owners, who'd been bad about upkeep, have it torched themselves? The place was cleared of contents, which were auctioned off before the fire; you can gape at the ruins and draw your own unofficial conclusions.

What is Skull & Bones up to in the Thousand Islands? Yale's shadowy society keeps an island nearby, reportedly given to them in 1949. May the Force be with you in finding out answers about this one. Certain facts about this elitest-of-the-elite group are known—it started in 1832, supposedly after the founder visited an occult society in Germany; 15 Yale seniors are tapped to join each year; and American leaders like George W. Bush and John Kerry have been members.

Still, Skull & Bones members take an oath of secrecy, and its rituals are a black box. Some hazard guesses about Deer Island—Atlas Obscura, for instance, reports that each initiate has to visit the mostly-in-ruins island as part of their long introduction ceremony. Do they simply party like college kids there, or is there more to it? The island’s uses remain unclear to this day.

All photos by the author unless otherwise noted.