We cruised by the Strawberry Island Lighthouse in Canada’s North Channel at 7 knots in a brisk 25- knot wind. I was aboard Henk Vanderhulst’s Precision 23, Go Gently, and he, despite his 80 years, was unwilling to risk his reputation for leaving the fleet in his wake. Henk worked the tiller with his foot as he reached forward to adjust the sails. “Put me to work,” I volunteered, but Henk, a singlehander for years, prefers to do things his own way.

I had just joined the Trailer/Sailors Association (TSA) for the second week of their annual cruise through the North Channel (having long heard of the area, I promptly invited myself along when I learned of the TSA cruise). We set out from Little Current, one of the few towns along the remote channel, which is bordered by the parklands and forests that make up the North Georgian Bay Recreational Reserve, and passed under its signature swing bridge at 1300. TSA cruisers first visited the area in 1987 and found that the shallow drafts of their 19- to 27-foot boats were ideal for exploring the area. Members now make a yearly pilgrimage—some from as far as Oklahoma and Kansas—to enjoy the sailing and camaraderie.

As the wind picked up and a storm cloud began trailing us to the anchorage, Henk considered shortening sail—until TSA president John Clement, on Taranui, and past-president Wayne Bell, on For Whom the Bells Toil, edged ahead of us. “Maybe not,” he said. Though the conditions were never as good as the week went on, the good-natured rivalry continued unabated.

The North Channel is a hundred-mile stretch of Lake Huron; it runs from St. Mary’s River in the west to Georgian Bay in the east and is separated from the main body of the lake by Manitoulin Island. The up-to-20-mile-wide channel is dotted with islands, and the rugged coastline provides a plethora of inlets. Anchoring is easy in the relatively shallow water. The islands are geologically diverse, some pink granite and others limestone with sandy beaches. The movements of the retreating glaciers that formed the Great Lakes thousands of years ago can be seen in the long striations in the rock, where boulders were dragged by the mile-thick sheets of ice, and in the erratics, rocks of foreign materials deposited by the glaciers.

The sailing season is a mere two months in these northern latitudes, and the North Channel’s rugged beauty and remote and diverse anchorages draw sailors back every year. But it’s not just the surroundings that make the TSA cruise grow (there were 52 registered boats this year, compared to 30 last year); camaraderie is a large part of the draw. Morning and evening radio nets provide a sense of security for less-experienced sailors, and shared local knowledge makes entering new anchorages less stressful. New sailors can learn about handling their boats and profit from seeing the many modifications that can be made to them to make trailersailing more comfortable. Some true newbies learn after gentle reminders from the group that road maps are not the same as nautical charts and that every captain must be responsible for his or her own boat.

IN JUST A WEEK I BARELY SCRATCHED the surface of the North Channel’s many attractions. I hiked up the cliff at Covered Portage to admire the magnificent view of the anchorage, explored the Benjamins’ booming rock and “fairy” grove, picked blueberries, swam, and enjoyed the legendary fish and chips in Killarney. We sailed through spectacular channels, picked our way through rockstrewn entries to secluded anchorages, and took the long way around islands to avoid turning on the engine. At night we sang around campfires.

Ultimately it wasn’t the marshmallows or the sunsets or even the inviting coves that made my week memorable, but my many hosts. I arrived on SeaQuell, the first of seven trailerable (read: small) boats I would sleep on throughout the week, with some misgivings. It is one thing to sail on a small boat with complete strangers, but the compact accommodations create an immediate and increased level of intimacy that can make for uncomfortable sleepovers. Rod and Ondine Brandon helped quell my fears. Their easy conversation, open manners, and well appointed boat set me at ease. The Brandons could be poster children for the trailersailing lifestyle, from the nautical throw pillows on their settees to their well-rehearsed division of labor for all onboard tasks and their dream of the ultimate trailersailing adventure. There was never a lull in the conversation as we feasted on steak, crab, and asparagus in the cockpit. They had planned for everything, and a simple curtain they hung next to the head allowed me to change my clothes discretely and have some privacy in the V-berth where I slept.

Another day I sailed with the Holderness family. Lindsey, 13, and Keira, 5, though not sailing enthusiasts, were at home on Teliki, their MacGregor 26, and Chris and Lenore Holderness recognized that sailing with other families made a two-week cruise possible. All the kids visited back and forth, swam together in the anchorages, and talked on the VHF. Lindsey served as the bow watch when we followed other boats into a tricky anchorage and handled the anchor when the time came, but she spent most of her time under way reading and drawing.

Teliki’s crew had benefited from the experience of other TSA members as they learned the ropes of sailing the North Channel. The previous year they’d been a bit shaken up by a bad storm that hit their Matilda 20, but the support of the TSA members who helped them anchor when they finally caught up with the main group—and offered soup and comfort to buoy their spirits—kept the experience from putting them off sailing altogether. They were back for the 2006 cruise with a bigger boat and greater confidence.

ONE EVENING I JOINED BOB AND JANE MULLEN aboard Atta Buoy, their O’Day 272, and was immediately introduced to Gene and Colleen Lindgren, who were rafted alongside on Harmony. Although the two couples belong to the same yacht club in Kansas, they really became acquainted on the North Channel cruise. I joined them for a farewell dinner before Harmony headed home and was impressed with the community created by the trailersailors.

Bob and Jane keep house on their 27-footer as well as most people do in their homes. I came onboard and was offered wine and hors d’oeuvres. I easily joined the conversation, and by the time they put me to work mixing the salmon burgers and tearing lettuce for the salad, I felt like I’d known them all for years. Jane had baked brownies in a pressure cooker and put together an impressive spread in her modest galley.

Shared meals are a big part of the North Channel cruise, and I was rarely the only dinner guest onboard. It was during these meals that the trailersailors exchanged tips on how best to bake onboard (some use pressure cookers or backpacker’s ovens), the best places to tie up on shore (some coves have padeyes driven into the rocks so boats can spiderweb themselves in with dock lines), and how to upgrade their boats to maximize space or performance. The singlehanders were often invited to eat and usually returned the favor with some of the liveliest stories about their sailing adventures. Henk, a particularly popular dinner guest, entertained us with tales of his circumnavigation of Lake Superior and read excerpts from articles he had written about his trips for “Clipper Snips,” the TSA’s journal of record.

Some group activities have gained a permanent place in the cruise schedule. Early in the trip, participants pool their fresh-picked blueberries and make batter for a pancake breakfast. The final night on the water is reserved for a potluck for which each boat puts together a dish from their remaining provisions (and a carefully chosen rock is awarded to the crew who managed to run aground that season). Communal hikes and dinghy explorations are also popular diversions, but nothing draws a crowd like dinghy bingo.

Dinghy bingo is a well-organized affair that involves laminated playing cards, dry-erase markers, and bingo number cards. The crew of each boat piles into their dinghy carrying a prize, drinks, and snacks, and the dinghies all raft around a single boat. The prizes are separated into a kid’s bag and an adult’s bag, and appetizers are passed from dinghy to dinghy as the crew aboard the central boat calls out the numbers. Outsiders who come upon the sea of dinghies are often perplexed; one onlooker thought the crowd of people with their heads bowed and the occasional exultant shout were attending a prayer meeting.

Wayne Bell explains the mystique this way: “The TSA is like a family. We don’t see each other for a year, but when we get together for the cruise things just pick back up where they left off.” Some members of the TSA travel across the continent with their boats, some trailer their boats to Florida or Mexico, some plan circumnavigations, and some singlehand for several months, but they return to the North Channel each year to join the group. After a week (and 14 boats), I felt that connection.

The TSA was founded in 1984 as a group where trailersailors could share their experiences and knowledge about sailing in inland and coastal waters. It now organizes a variety of trips for trailersailors and maintains a Web forum for the exchange of maintenance and sailing tips. Learn more about the association at trailersailors.org.