When their boats can’t float, Shelter Island sailors glide

The winter of 1934 on Shelter Island was cold, cold, cold. Did we mention cold?

While Islanders stayed close to their stoves and out of the wind, Shelter Island ice-boaters gleefully watched the February temperatures drop below zero and stay there for days. The ice was so thick on roads that Islanders had to walk almost a half mile to board the ferry to Greenport, and mail and supplies came in on sleds.

Even in the early 20th century, most winters were not cold enough for ice boating, but the memory of flying across the ice steering a device powered by the wind is so compelling that people who love to slide never stop dreaming of more frozen days.

We know from the diary of 26-year-old D. Harries Young (transcribed by Mike McClain for the Shelter Island History Museum) that he spent most of the morning of Jan. 4, 1934, in the attic of his home at 55 Cartwright Road locating the “accoutrements” (sails and rigging) of his iceboat. He was working for the Shelter Island Light Company, but his preoccupation with readying his iceboat and helping his friends with theirs filled his diary in January and February 1934, including daily updates on the temperature and condition of the ice. 

Finally, on Wednesday, Feb. 14, with the temperature at 2º, he succeeding in sailing for an hour or so: “My craft, the first to show her wings on the harbor ice, and a right welcome sight it was for me, too; eleven years having elapsed since her last appearance on Coecles Harbor. Here’s hoping better days for the sport lie ahead.”

Betsy Colby, co-chair of the Shelter Island Yacht Club Race Committee, grew up ice boating with her father with the Hudson River Ice Yacht Club. (HRIYC). He was part of the consortium who owned and restored the Jack Frost, the largest ice boat (50 feet) in North America and in 2003 was one of the challengers for the Van Nostrand Challenge Cup, a vintage iceboat race that has only been held four times (1891, 1978, 2003, & 2026) and was recaptured by the HRIYC in February 2026.

John Needham has five iceboats, but his favorite is a Gambit, a two-person craft that allows him to share the thrilling experience of “hard water sailing.” Islanders Herb and Hoot Sherman won the Gambit in an auction and, always eager to share the experience of iceboating with others, decided John should have it. John said, “I will always remember Hoot Sherman’s words, “John … take the Gambit. Get out there. You’re the sailor.’”

John took that charge seriously, mentoring other sailors in the joys of iceboating. He tells them that unlike “soft water sailing,” the winds you encounter iceboating are forces of nature the sailor must wrangle without the benefit of ripples or whitecaps to show where they are coming from, or how hard. 

“On an iceboat there isn’t any of that warning. You can get shot out by that gust like a slingshot,” John said. “In light air, you may only move gust to gust. At the end of the day when it gets quiet and the sky turns pink or orange, the ice turns pink. A lovely experience.”

He remembers iceboating in the 80s and 90s as “very social, often with a barrel fire on the beach to warm your hands, and Judy Sherman bringing a kettle of clam chowder.”

People on Shelter Islander never miss an opportunity to have fun outdoors, especially during the winter when they’re not tending the land or catering to second homeowners. When North Ferry manager Elliot Dickerson, (1906-1997) was asked in an oral history interview what people did for fun in his youth, he answered, “Iceboating.” Another enjoyable characteristic of iceboating on Shelter Island that John Needham says is unique to Shelter Island is the high percentage of women among iceboat enthusiasts, including Michelle Congdon, Denise Fenchel, Kathy Gooding, Susan Klenawicus, Judy Sherman, and Laura Tuthill.

To learn any sport well, you need a coach, and Harbormaster Butch Labrozzi credits John Needham as his teacher and mentor for iceboating, which is one of his passions. This year’s conditions for iceboating are the best in more than a decade and Butch is still taking advantage of the opportunity. 

“It doesn’t happen all the time,” he said. “When it happens around here, I focus on trying to get as many days as I can being out on the ice.” On Valentine’s Day he traveled to Mecox Bay on the South Fork and spent the entire day sailing up and down the bay, enjoying every run. “I could hear the waves crashing on the ocean side of Mecox,” Butch said. “It was a calm day, with very light winds.” He was planning to head back to Mecox soon, weather permitting.

Connor Needham, 33, the manager of the Coecles Harbor Marina, is a competitive sailor, and grew up on the water. “One of my wife’s friends calls me ‘the water

 cowboy.’” Connor took advantage of the January/February cold spell to pioneer another way to slide when Shelter Island develops hard water: snowkiting. 

“The kite is something I’ve been doing for 15 years on a wakeboard in the water,” Connor said. “Snowkiting is the same concept, just on a hard surface, not liquid.”  

When Connor locks his feet onto his board, and the kite — 60 feet above him — fills with air and pulls him across Coecles Harbor at 30-plus miles per hour, it’s exhilarating to watch. 

It helps you understand why so many Islanders yearn for the bone-chilling temperatures and freezing rain that make the bays look like the handiwork of a giant Zamboni, where they can glide and slide and play.