A Thousand Adventures

Castles, secret societies, shipwrecks, British forts—and tons of great boating!

Ontario’s Thousand Island archipelago is made up of more than 1,800 islands scattered along the St. Lawrence River between the Canada-US border. The region is a boater’s paradise and the perfect spot to spend a day or two exploring and relaxing. The reasons for visiting are endless: the vast archipelago includes the smallest inhabited island in the US, an island owned by the Skull and Bones secret society, and an island with the ruins of a British fort that was captured by the Americans in the War of 1812.

It’s the home of Thousand Islands National Park, one of Canada’s oldest. There are two boating museums, a bunch of shipwrecks, and even a few castles including Boldt Castle, built by the proprietor of New York’s Waldorf Astoria for his wife. And it’s also the spot where, the story goes, Thousand Island salad dressing was invented. There’s even a Walt Whitman poem about the region called “A Song of Joys” for any literary types out there: 

O boating on the rivers,
The voyage down the St. Lawrence, the superb scenery, the steamers,
The ships sailing, the Thousand Islands, the occasional timber-raft
and the raftsmen with long-reaching sweep-oars,
The little huts on the rafts, and the stream of smoke when they cook
supper at evening.

Whether you’re a history buff, boating enthusiast, lover of shopping, seafood, and sunsets, or just looking for some family fun, there’s something for everyone. So where to begin? According to Corey Fram, Director of the 1000 Islands International Tourism Council, who was born and raised in the region, it’s easy for visitors to plan a trip according to their interests—and their boat. 

Planning a trip to A boater’s paradise

There are plenty of spots from which visitors can launch their 1000 Islands adventure. Popular waterfront communities along the river like Brockville, Ontario cater to boaters, and have transient docking and mooring options that allow travellers to explore each town. 

“Sailors often prefer the more open portions of the St. Lawrence River, where it starts at the end of Lake Ontario between Kingston, Ontario, and Cape Vincent, New York,” says Fram. “The wind can be pretty fierce up there and it's perfect for wide-open sails.” Power boaters, however, may prefer to wind their way among the islands in the narrower parts of the river around Gananoque, Ontario, and Clayton and Alexandria Bay on the US side, he notes.

And of course, in a place called the 1000 Islands, getting off the mainland is a must! “Boldt Castle on Heart Island is a six-story Rhineland-style mansion that tells a tragic love story,” says Fram of the region’s most popular attraction. “Restored to its 1900s construction, the castle should be atop any boater’s list.” The ominously named Dark Island also has a must-visit castle: Singer Castle has dungeons and underground passageways available to tour. Travelers can also rent an entire wing of the place if they want to stay overnight—the Royal Suite sleeps six. 

Island camping and historic hotels 

While towns along both sides of the river offer tons of overnight accommodations, adventurous travellers can also stay on the islands themselves. Aside from Singer Castle, options include a quintessential Canadian camping experience—Thousand Islands National Park offers more than 20 islands for campers to choose from. Boaters can grab a camping permit at a payment kiosk on arrival and get ready to enjoy a night under the stars. Parks Canada even offers equipment rental for anyone who needs it. 

Visitors can also stay on the largest island in the region at the General Wolfe Inn (also commonly called the Wolfe Island Inn), which offers a restaurant, waterfront views, and free boat docking, while on Wellesley Island, visitors can enjoy dinner and accomodations at the charming Wellesley Hotel Restaurant & Pub built in 1903. Both Wolfe and Wellesley islands can be accessed by boat or car. 

Staying on the mainland is easy too, with its mix of hotel chains, cottages, and B&Bs along both sides of the border. “Kingston is our largest city and has an abundant variety of chain hotels, locally owned and operated properties, and a healthy mix of cottages and bed-and-breakfasts,” says Fram. He also suggests checking out Gananoque, Ivy Lea, Rockport and historic Brockville on the Canadian side or Alexandria Bay, Clayton, Cape Vincent, and Sackets Harbor on the U.S. side for a spot to spend the night. 

Fram offers a handy tip for where to enjoy the best views. “Canadians get better sunrise views, whereas the American mainland is the optimal angle for sunsets,” Fram says. “All that goes out the window on a boat, though, where you can chase the sun for the best looks.” 

Border crossings are a breeze

The US and Canada share the world’s longest undefended border—and there’s no better place to experience this friendly fact than the 1000 Islands region. With the islands scattered along both sides of the border in the St. Lawrence, most boaters will pass back and forth across the invisible boundary without realizing it. “You don’t need border-crossing documents to traverse the water, border but requirements take effect as soon as you touch land, a dock, or drop anchor on the opposite side,” explains Fram. “Manned Customs stations at places such as Boldt Castle make checking in easy and there are unmanned call-in locations in many communities on both sides of the border,” he says. Just ring up immigration and let them know you’ve stopped in for a bit. What could be easier? 

Of course, visitors should always be mindful of the laws of the land and be prepared in the event of a vessel inspection from police in either country (Canadians should remember that marijuana remains illegal in the U.S., for example.)

Festivals, events, parties, and tall ships

Potential visitors will want to keep an eye on the calendar if they want to take advantage of one of the big festivals happening in the region. Big annual festivals in the region include Pirate Days in Alexandria Bay (the area has a long history of pirating), the Limestone City Blues Fest in Kingston, the Antique Boat Show & Auction in Clayton, French Festival in Cape Vincent, the Can-Am Fest in Sackets Harbor (celebrating Canadian-American relations) and the 1000 Islands International Charity Poker Run. The tall ships festivals also stop in Brockville, Kingston, and Clayton. 

Between festivals, historic towns, and the thousands of islands to explore, the 1000 Islands region will keep any visitor happy for days—or even weeks—at a time. And of course, it’s always a good idea to take some photos for the folks back home. “Checking social media reminds us that the rest of the world is awed by where we live,” says Fram of his birthplace. “When you have sunsets like we do, everywhere is Instagrammable.” First-time visitors can visit https://visit1000islands.com/first-time-visitors/ for more info and to help plan their next trip. 

About Jennifer McCartney

Jennifer McCartney is a New York Times bestselling author. She has written a number of books including So You Want to Move to Canada, Eh? Her writing has appeared in The Atlantic, Vice Magazine, Teen Vogue, and CBC.

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