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It was early evening, but the darkness felt like midnight. Our stout, 38-foot Marine Trader trawler Mazurka chugged along, a little toy boat in the middle of the biggest and coldest of the Great Lakes.

We had spent the summer boating in the endless light of the 47th parallel. Now, in the last weekend of September, the black sky enveloped us. In the east, Mars shone like a beacon above the Apostle’s Sand Island, almost at the closest point in the planet’s orbit to Earth.

My husband, Mark, sat at the helm. Our 6-year-old slept in the aft cabin. Our 10-year-old slept in the forward V-berth. Our 8-year-old daughter found the dark and the cold air exhilarating. Wrapped in a blanket, we sat together at the bow. She looked up.

“What is that?”

Above us, a thick white scarf stretched across the sky, a glittering shawl pulled by one of Apollo’s muses.

“That’s the Milky Way,” I told her.

Mouths agape, heads back, we stared up at the night sky, watching our galaxy extend from Minnesota’s Sawtooth Mountains across the dome to Wisconsin’s Chequamegon-Nicolet National Forest. I told her of millions of stars, how we are positioned in one tiny corner of the huge spiral-shaped galaxy. The engine purred on.

Cold-weather boating wasn’t a new concept for Mark and me, but after all we’d learned, we were happy to share the experience with our family. When we lived as year-round liveaboards in Chicago (15 years ago, before kids, in another life…) the annual migration from lake harbors to the river was marked by one glorious month called “Late Leaver Status.” We first experienced it on a day when, just a couple months married, Mark charged down the dock waving a paper in his hand. “We got Late Leaver Status!” It was a single month from October 15 until November 15 when boats were granted one more month on the water.

And oh, it was glorious. A lakefront that hosts an endless party in the summer months—busy docks, crowded parks, a path jammed with bicycles, runners, in-line skaters and dog walkers—transforms into an isolated getaway. November in Chicago can be cold and dark, with millions of residents hunkering down inside. Except the die-hard Late Leavers who revel in the autumn lakefront as if it’s all theirs. And for a single month, it really seemed like we were the only ones on that billion-dollar property.

The final drive inland to our winter marina on the Chicago River was cold, sure, but oh, so worth it, and it was exhilarating to be out on the lake when the wind was whipping around us. I think I laughed the whole way.

After we moved to Lake Superior in 2008, we followed the saying among old-school “yooper” boaters (who, like my husband, hail from Michigan’s Upper Peninsula) to get off the lake by August 15. The wind shifts and the waves get nasty; best to clear out and leave it to the hardy fishermen.

Then we noticed that Labor Day weekend tended toward warmth and calm water, which started stretching later into September and even October. There’d be some pretty rough weather, then suddenly a summery stretch. Venturing out on the big lake later in autumn with a close eye on the weather has been rewarded with bug-free days and campfire-lit nights, plus a camaraderie of gratitude among the late-season cruisers. We shouldn’t be out this late in the season, but here we are, getting away with it.

Built in 1881 from sandstone quarried right at the site, the Sand Island lighthouse is staffed in the warmer months by park service volunteers—and a friendly ghost—who love to talk about the people who once lived and fished on the island. They’ll also share where to see the abandoned Ford Model T and what to do if you encounter a bear on the way.

Built in 1881 from sandstone quarried right at the site, the Sand Island lighthouse is staffed in the warmer months by park service volunteers—and a friendly ghost—who love to talk about the people who once lived and fished on the island. They’ll also share where to see the abandoned Ford Model T and what to do if you encounter a bear on the way.

That late September night, we followed Mars all the way to Justice Bay, just inside the northeast corner of Sand Island. An armada of resting boats greeted us—surprising, as we expected to be the only ones. Anchoring in the inky black of night is not easy. Luckily, we were familiar with the bay and its sandy bottom. The biggest challenge was maneuvering around our fellow boaters who also were taking advantage of the late-season goodness.

Eric Thomas, general manager of Barker’s Island Marina in Superior, Wisconsin, and CEO of Sailboats, Inc., told me how anchoring in the autumn requires different skills because fall winds can be stiff. He recommends using an anchor snubber, which is basically a short length of cord attached to the anchor chain and to another point on the boat. It will take the load off the windlass.

“Never ride on your anchor line just on the windlass,” Thomas said. “We’ve seen a lot of accidents with people new to boating. [They put] the clutch on a windlass and end up spooling their rode in a stiff wind and losing their boat on a beach.”

Thomas has seen a lot of weather changes in his three decades at Barker’s Island Marina. (The past seven as general manager and co-owner, and 23 years before that as service manager.) “Starting back in the ’80s when I came up here, we would count 90 days of northeast wind consistently in April, May, June,” he says. “Just not the case anymore. The lake is warmer, and the weather is warmer.”

The fall weather is much more dramatic, he said: “We get these big swings. We used to have a normal transition. Now, you can boat later, but you got to watch your windows. We get these big cold snaps in late October.”

Barker’s Island has set Halloween as its haul-out deadline, even if you can boat into November. They have hundreds of boats to put up, after all.

“Last few years, we’d stray into mid-November hauling boats out and get a big cold snap, and it caused a lot of grief,” he said. “We’d have 50 boats in the water. Owners get nervous when they’re still in the water.”

Enduring some cold snaps may be worth it when they’re followed by a long weekend of 50-degree temperatures.

If you’re going to stay in the water till last call, make sure your systems are ready to deal with the cold snaps, and pay close attention to the weather. Cockpit showers and a deck wash will crack and freeze in big cold snaps. Powerboats that have large engine intake louvers need to be opened and covered. “Stuff a towel in there temporarily to keep cold air from blowing in,” Thomas said. If it’s going to get really cold, drain the heat exchange, just in case.

“Water is warm. Water is your friend,” Thomas said. “Anything below the waterline is pretty safe from something a day or two long, as long you’re not having 30 knots of wind blowing through engine louvers.” But the wind can be vicious. “We see a lot of canvas get destroyed in fall,” he added. “It’s been up all season, getting brittle, and a fall gale is the end of it. It’s not likely you’re going to be up on the flybridge with just a bimini, so take the bimini off for the fall, and drive from that lower station. It’s the beautiful season for those with dual-station helms.”

As a sailor, Thomas is fond of autumn boating because, he said, “It feels like you’re stealing time. If I can keep a boat in the water, the fall colors are spectacular.”

That last weekend of September, the yellow coins of birch leaves were just starting to flutter at us. The maples and oak would hold out longer. On a Saturday morning, though we’d visited the island dozens of times, we took a trail we’d never explored. The autumn air, the smell of the leaves, made it seem like a different island. No black biting flies, no mosquitos. The frenetic summer energy had calmed into the autumnal descent. The day was warm, the sunlight soft. Something about the last bittersweet hurrah prompted us to take the lesser-known path. Beyond an enormous ripe apple tree and a lot of fresh bear scat, we were rewarded with the discovery of an abandoned Victorian home with a tractor out front. Surely the National Park Service had been there plenty of times, but it was new to us.

After lunch on the flybridge, Mark spotted something on the horizon. “It’s the Falcon!” We turned to see a sailboat rounding the bend. At the helm was our friend Dave Tersteeg, harbormaster and parks and recreation director for the town of Grand Marais, Minnesota.

Grand Marais Harbormaster Dave Tersteeg sailing solo at the end of the season.

Grand Marais Harbormaster Dave Tersteeg sailing solo at the end of the season.

Falcon and Mazurka raft together in Justice Bay.

Falcon and Mazurka raft together in Justice Bay.

We had emailed about the amazing weather forecast and the possibility of meeting up that weekend, and the stars aligned. The Falcon rafted onto Mazurka, and snacks and fizzy water were passed around.

For Tersteeg, being so far north means it almost always feels like he’s boating in fall. “Most of my sailing is on cold, gray water,” he said. “I find summer by sailing to the Apostle Islands in August. The return trip home usually involves an abrupt change of seasons midday. The water goes from blue to black halfway across. The foulies come back out.” In August, he sees green shores leaving the islands and a yellow-tinged ridgeline approaching Grand Marais. “I sense the end of boating season is near, pulling into the harbor with numb hands.”

Business at the Grand Marais municipal marina generally flows with what he called the “on and off” cycle. Both seasons seem fleeting. On season is July Fourth to Labor Day; off is everything else. After Labor Day, pleasure cruising definitely winds down, and the few boats Tersteeg sees are heading to winter storage destinations. “The exception to this is the local, sporty anglers,” he said. “They have steering wheels inside, cabin heaters and lots of lures on the bulkheads. They go to Isle Royale in the fall and catch really big fish.”

On Mazurka, we have ongoing jokes about wearing a life jacket and hypothermia. (What do you do if your rice burns on the stove? Put on your life jacket!) But underlying the jokes is a grave earnestness. Even the strongest swimmer can succumb to hypothermia, and the cold water at any time of year is not to be messed with. But in the fall, its threat is even more serious.

The U.S. Coast Guard on Lake Superior emphasizes the risk of hypothermia and the importance of PFDs into the autumn months as part of its paddle safety and recreational boating safety initiatives. The Coast Guard expects boaters to be out on the water through the end of September, when the agency switches to ice safety messaging.

“When folks see nice weather in September and it’s 70 and sunny, they hop in their boats and go,” said Lt. Cmdr. Abbie Lyons, waterways and incident management chief for the Coast Guard in Duluth, Minnesota. “We say dress for the water, not the weather. If the water is 50 degrees, you’re still at risk for extreme hypothermia. It’s tempting to get out on the lake on a hot day—not always easy to get back when a storm rolls in.”

Even on the boat, you have to be ready for the cold. Tersteeg’s advice for autumn boating: “You’re either OK with being cold or you stay home.” He added that his wife stays home, “and we’re cool with that.” A cabin heater is a must; so is hot tea and coffee. “I store my winter wardrobe on my boat with lots of really warm socks, hats and mitts,” he said. “My hands generally run cold, so I use big leather choppers with wool liners. As boaters, we always watch the weather; in the fall, we really watch the weather. I see more lakers plying autumn waters, perhaps due to harvest season. It’s the season to savor the luxury of boating, to look back on the summer and take it all in. Facing six months of winter storage, I always go for that final victory lap just before haul out.”

Mazurka basks in the early sunset light on the last cruising weekend of the season, while her crew readies a campfire on shore. The inevitable end of another extended boating season approaches.

Mazurka basks in the early sunset light on the last cruising weekend of the season, while her crew readies a campfire on shore. The inevitable end of another extended boating season approaches.

That final victory lap is also a good time to make a realistic chore list for what needs to get done over the winter, Thomas said.

“Make that chore list while you’re using the boat and not under the Christmas tree,” he said. “Under the Christmas tree, you’re under the influence: You want new toys. You got to do your chores first.”

And just as the boating season extends longer, it’s also starting earlier. This year, for instance, Thomas found that it started a full three weeks earlier on Lake Superior. The water is warmer overall, he said, a situation that lets air attach to the water, making for more western winds year-round. The pattern is warming things up and allowing the season to start in the spring.

For a season as short as we have on Lake Superior, we’ll take every extra minute we can get.

That autumn Saturday night, we had s’mores around a campfire on the beach, then went to bed early beneath the stars. Sunday morning, we left Justice Bay ahead of the Falcon.

“Watching you guys disappear over the horizon on Sunday morning was also a very autumn moment,” Tersteeg said. “Boating season was coming to the inevitable end. I saw it motor away.”