New York and Ontario’s Castle-Crowned Island Region with Stunning River Views: A Dreamy Summer Escape

Chances are, you’ve heard of Thousand Islands salad dressing, a famous (or infamous, depending on your taste) sauce. However, did you know that Thousand Islands, the dressing, actually originates in Thousand Islands, the place? This chain of islands on the St. Lawrence River, on the U.S.-Canadian border, is much more than the namesake of the dressing, however. Charming towns, Gilded Age mansions, outdoor adventure, celebrity retreat, and even a national park make this one of North America’s best secret summer vacation spots.

The Thousand Islands (technically over 1,800 islands) have a long history, first as the home of Indigenous groups, like the Iroquois and Algonquin nations, who refer to the region as “the Garden of the Great Spirit,” or “Manitouana.” The islands were the site of many skirmishes during the War of 1812, between the United States and Canada, then part of the United Kingdom. Several of these battles are commemorated throughout the islands in former military fortifications. At the end of the 19th century and into the early 20th century, during the prosperous Gilded Age, many wealthy and famous people vacationed in the Thousand Islands, seeking a close respite from New York City, some 350 miles (560 km) away. During the American Prohibition, the islands hosted many bootleggers or “River Rats” transporting their illicit goods. 

Nowadays, you’re unlikely to attend a Gilded Age Ball, evade pirates, or hunt down a speakeasy (although you’ll find plenty of distilleries and wineries!), but the islands still retain much of this historical charm. Each inhabited island has its own unique past and present appeal, along with plenty of legends, from hidden treasure to shipwrecks to long-ago celebrity visitors. The islands have also become an ideal destination for adventurers, attracting scuba divers, kayakers, and canoers, along with avid anglers.

The Thousand Islands is home to several overlooked small towns, some of the most beautiful in New York, like Clayton and Alexandria Bay. Clayton, once a bustling shipbuilding port, is home to several interesting museums, like the Antique Boat Museum, as well as beautiful historical streets and small-town charm. Alexandria Bay is ideal for families, with activities like mini golf, and also provides easy access to the famous Boldt Castle on Heart Island. The best way to explore the islands is by boat. Since it’s not the Gilded Age anymore, you probably don’t have your own boat — but there are plenty of boat tours and cruises that take you to castles, mansions, or lighthouses, like the famous Rocky Island Lighthouse, on a small island between Clayton and Alexandria Bay. 

One of the highlights of the Canadian side of the Thousand Islands is Thousand Islands National Park, a pristine section of preserved wilderness with rocky shorelines, wooded isles, and river views. Kayakers especially love the park, paddling between campsites on different uninhabited islands. There’s also Wolfe Island, one of the islands accessible via ferry, home to the charming Canadian town of Marysville, best reached by bicycle from the ferry landing.