Travel & Outdoors

A Rare Window Into the Rip-Roaring Chesapeake Tradition of Iceboating


For the past two weeks, “hardwater sailors” took advantage of the cold weather to partake in this little-known Maryland ritual. 


Most Marylanders woke up this past Monday morning with a deep sigh of relief. In late January, a winter storm whisked into the region, bringing snow and sleet then a serious cold spell, suspending residents in an unusual tundra for the better part of the past two weeks. The ice is just now beginning to melt, and as the mercury inches back into the 40s, the common sentiment seemingly everywhere is “finally!”

Not everyone is celebrating, though. On the Eastern Shore, it’s a bittersweet moment for a for a few hardcore locals like Michael Keene, who spent most waking hours of the past 14 days outside, taking advantage of a rare phenomenon: the Chesapeake Bay, frozen solid.

“There’s going to be a grieving period,” says the 61-year-old Talbot County native, sitting on a wide but waning patch of ice in Claiborne, where he’s been serving as a sort of unofficial mayor since the blizzard rolled in that weekend.

In the days immediately after the storm, once the accumulation settled and the roads started being cleared, Keene looked again at the coming weather. From his experience—as a longtime sailor, boatbuilder, and log-canoe racer—it takes five nights of frigid temperatures to freeze the local shorelines. And this particular storm, with its northwest winds and lingering cold, he figured, would surely pack his favorite cove in fast and tight. To confirm that hunch, within 48 hours of that final snowfall, he went out there and dug a few holes into the ice.

“At four and a half inches thick, it was game on,” says Keene, who the next morning loaded up his small wooden boat and set out to quite literally skate across what he and his group of fellow adventure-seeking sailors call “hard water.” He’s been at that icy waterfront every day since, experiencing the sheer thrill of iceboating.

Here, old thick piers emerge from the shallows, telling of Claiborne’s heyday in the first half of the 20th century. The tiny hamlet was then a bustling hub, with steamboats ferrying passengers back and forth from the western shore. After the Bay Bridge was built and automobiles took over, the community fell into a sort of slumber—mostly known by locals for its boat landing and sandy beach.

Without a doubt, the past few weeks have been the busiest it’s been in ages. Each day, the crowd grew larger in Claiborne, its usually sparse waterfront parking lot at times filled to the brim. After all, winters like this don’t happen every year. And it’d been decades, the old-timers say, since the ice has been this good.

“It’s no big science,” says Keene, surveying the simple lines of his fragile-looking iceboat. At 12 feet long, these miniature vessels are essentially sleds, their lightweight hulls fit with a lone sail and three skating blades, the one in the front attached to a tiller for steering. Bundled up in ski gear—often practical, sometimes fashionable—sailors lay down inside, and with a quick push, the canvas catches the wind. They soar off on the ice like swallows, swooping in around the landscape’s curves, shooting out toward the jagged edges near open water.

Iceboat details in the Claiborne cove.

The smoother the ice, the faster the sailing, and this year, that frozen water had an especially well-polished texture. With little friction, the boats simply glide across the surface, only needing the slightest breeze. They move three and a half times faster than the wind, easily reaching speeds of 50 miles per hour.

“You get these bursts of excitement,” says Pete Lesher, historian at the Chesapeake Bay Maritime Museum in nearby St. Michaels, who sailed several days this season, including a few runs with his son. “In part because you can’t be out here that long. It’s bitter cold and the wind chill goes right through you. You go out and back, you scream around a few times, and then you say, ‘Okay—who’s next? I’ve got to go warm up.’”

Popularized along the Hudson Valley and Great Lakes, iceboating is at least a century-old tradition on the shores of the Chesapeake.

I have never known such ice as there is now…and we are sailing everywhere,” wrote one Talbot County boatbuilder in 1917, though other accounts date back more than a decade earlier.

Early on, most vessels were homebuilt, but over time, they were replaced with a standard “DN model,” named for the Ice Boating World Championship’s sponsor, The Detroit News. In the winter of 1977, snowfall complicated conditions in those northern states, sending the competition’s organizers in search of a new location.

In a twist of fate, they landed on the Miles River, just around the bend from that Claiborne cove, as Maryland was in the midst of a historic freeze lasting some 58 nights.

They called it a perfect day. The windchill factor was minus 15 degrees. Smallcraft warnings were posted…On downwind tacks the [iceboats] were reaching speeds of 80 miles an hour,” wrote The New York Times. “Hardwater sailors are a closelyknit fraternity. They spend winter weekends in search of good ice.”

Indeed, that year, iceboaters from around the world descended on Chesapeake, inspiring locals like beloved Carpenter Street Saloon owners John and Diana Mautz to find their own boats to race. Theirs would eventually find its way into Keene’s possession. He points out the original mahogany trim and his later repairs, being part of the region’s long lineage of maritime craftsmen.

“My niece recently asked me a good question, though: Is it truly a boat?” says Keene with a smile, having learned the hard way that the answer is “sort of.” He’s broken through the ice before, and luckily, the vessel did float, bobbing enough to keep his upper body dry until he could be rescued.

Michael Keene and Jim Richardson with the iceboat fleet.

Unsurprisingly, this fast-flying sport does come with its fair share of dangers. First and foremost, there’s the fear of falling in, and over the years, there have been closer calls than Keene’s in deeper waters. Sailors also watch out for heavy gusts and try their hardest to avoid splintering collisions. Precautions are implemented, such as sailing in shallow depths, on stable ice shelves, and never going out there alone. Flags are also planted to show the course’s guardrails. Most practiced participants wear helmets, too.

Jim Richardson is a veteran iceboater who took up the pastime in the early ’80s, not long after he moved to Claiborne—his home above the town’s old general store now serving as the de facto headquarters for warm meals between races. This year, he ran aground about a week in, coming into the cove a little too hot on a blustery day, breaking some bones in the process.

“Sometimes you’re like a leaf,” says the 78-year-old from his the warmth of living room, his right foot now strapped into an orthopedic boot. “I like the speed, and sort of being on the edge. I’m not sure iceboating is for anyone who always likes to be in control. And of course, the other day, I found out exactly what it means to not be.”

“No harm was done to the boat, at least,” says Keene, whose skillset made him the fleet’s go-to mechanic, addressing all the wear and tear that accumulated over two weeks of sailing daily. “Although another sailor took it out and wrecked it yesterday.”

He and Richardson are old friends and organically became the ringleaders of these rip-roaring activities. That first weekend, they threw a party on the frozen cove, transforming its rock-hard shelf into a communal living room, equipped with benches, blankets, a floral carpet, and a wood-burning fire in a 50-gallon drum while a half dozen ice boats crisscrossed against a blazing sunset in the distance.

Sailors getting ready to ride the wind.

It didn’t take long for word to get out on social media. More and more cars started flocking to Claiborne—from Annapolis, Baltimore, even as far as Deep Creek and Washington, D.C. And the cove filled in not only with iceboaters but ice-skaters, ice-hockey players, one rogue bicycle, and countless wide-eyed spectators, some days as many as 100 people, all convening to bear witness to this fleeting spectacle.

And here’s the thing about iceboating: once you see it, you want to do it, too. He and Richardson took a flurry of first timers out for inaugural rides, including reporters from the local and national news. They also lent their boats to experienced sailors brave enough to navigate the cove on their own. A few fanatics even went home and bought used vessels online, willing to wait however long it might be until the next deep freeze.

“This doesn’t happen very often—maybe next year, who knows, or maybe not for another 50,” says Richardson. “These weeks have been very special.”

Keene gives an initial push.
An iceboat under sail.

Indeed, just standing on the frozen Chesapeake is a singular feeling. At first, for the uninitiated, there’s some trepidation, as if it might melt beneath your feet in a moment’s notice. But before long, that shifts into a sense wonder, seeing the ice’s pluming patterns up close, its old cracks healing over, the new ripples forming from the slowly shifting tidewater.

This winter, even the most warm-blooded and risk-averse eventually stepped onto the frozen water, with this welcoming crew encouraging a newfound appreciation for the cold.

“I’ve been thinking about what the ice does to us,” says Keene, who recalls winter ice-skating with his family on nearby Peachblossom Creek as one of his fondest childhood memories. “It’s this magical way to connect with nature. And to one another.”

Sailors seizing every hour of sunlight. 

On Monday afternoon, his was the only boat sitting on the Claiborne ice, soon to be named Diana-mite after its previous owner—who was, by all measures, a pistol. He whipped around the cove one last time that morning, but now, the wind had died down, with barely a cloud on the horizon. By tomorrow, the temperatures would once again be well above freezing, bringing that inevitable thaw.

A little bit later, Lesher appeared in a suit and tie, hoping to get one last glimpse of it all on his lunch break.

“So this is it—it’s over?” he called out to Keene from the sandy shoreline before carefully traversing the ladder laid down over slushy puddles to reach the dwindling ice sheet.

“We’re sitting here ’til the wind comes up again,” Keene yelled back, a glimmer of melancholy in his voice, knowing there’d be nothing but calmer air and warmer days ahead.

That night, Keene would stay out there until just before sunset, ultimately breaking down his boat, pulling up the flags, and heading home. He’ll be back to Claiborne in no time, teaching yoga classes at the local village hall and hunting for arrowheads with his partner. Before spring arrives, he’ll bring out his stand-up paddleboard, and come summer, he’ll swim in the open water, where not that long ago, he was nearly flying.

Still, he’ll miss all the rush and ruckus.

“I also like the solitude,” says Keene. “The other morning, I just texted my friend, Jack: ‘8:30?’ The two of us got here. We had the ice to ourselves. Perfect conditions. Good wind. Then I came out Friday morning, put on my skates, and just soaked it up all by myself.”