If you've only ever associated "Thousand Islands" with the tangy salad dressing made popular in the 20th Century, you're not alone. Even the most geo-savvy are unaware of the sprawled motley of islands—from which the dressing derives its name—bordering New York and Ontario, Canada. The picturesque area once rivaled the Hamptons during the Gilded Age as New York’s playground for the super-rich, marked by island castles and stunning coastal mansions still seen to this day. And the name of this 50-mile archipelagic region is no hyperbole — there are 1,864 islands interspersed in eastern Lake Ontario and the St. Lawrence River, ranging from 40-square-mile plots to tiny outcrops supporting one tree. If you’re unfamiliar with the “freshwater boating capital of the world,” here are a few darn good reasons to pack your bags and visit one of the North America’s best-kept secrets.
1. Fascinating History and Maritime Museums
From the Remington Museum in the town the premier artist once lived to several sites for the Underground Railroad, The Thousand Islands pack quite a punch for historical attractions. Oswego’s Fort Ontario, now a state historical site, had been destroyed and rebuilt several times between the French and Indian War and the Civil War, and once sheltered 982 Jewish refugees during World War II under President Franklin D. Roosevelt’s orders; the local Holocaust survivors are honored in the excellent Safe Haven Museum located seconds away from Fort Ontario. A prime standout is the Antique Boat Museum in Clayton, a world-class collection of more than 200 boats, yachts, and other interesting artifacts including Dr. Seuss’ early motor lube ad illustrations, preceding his legacy as an iconic cartoonist.
2. Picturesque Island Castles
Located off Alexandria Bay, the 127-room Boldt Castle allows visitors inside the ambitious “love gifting” from George Boldt, Waldorf-Astoria’s original hotelier, honoring his wife Louise. Though George halted the Rhineland-style island estate’s four-year progress upon his wife’s death in 1904, Boldt Castle has undergone vigorous restoration efforts and remains the region’s most popular attraction. Further up St. Lawrence River tiptoeing the US/Canadian border is Singer Castle, too a century-old turreted juggernaut founded by a self-made millionaire, former President of Singer Sewing Company’s Frederick Bourne. Travelers dreaming of a night spent in a medieval-inspired castle are in luck: guests can book Singer Castle’s full-wing Royal Suite overnight and, after visitor hours, have the 28-room castle and its lush island acreage to themselves.
3. Unfussy Local Food & Dining
The sizeable region retains its charming small town flavor with very few national chain eateries. In the Oswego, New York farmers market, Ontario Orchards—one of New York’s largest—is perhaps the finest example of Thousand Islands’ “proudly local” spirit, featuring many goods made on-site and at nearby farms and local vendors. With its own bakery, nursery, farm, and apple cider mill, it’s a can’t-miss for agri-tourists in New York State. Cheap and cheerful Rudy’s Lakeside Drive-In is a quintessential seafood experience (also great for chili dogs and burgers) with sweeping Lake Ontario vistas, while Tin Pan Galley in Sackets Harbor adds flair of whimsy in its romantic courtyard setting and delectable menu choices. How can you not get excited over crème brûlée French toast or a creamy crab cake benedict?
4. Visit Two Nations in One Trip
With the St. Lawrence River bottlenecked between the U.S. and Canadian coastlines, visitors could easily slink in and out of international borders on the water—as long as you don’t dock at the opposite country. Taking Uncle Sam Boat Tour’s “2 Nation Tour” will bring you across the (invisible) international line to see Canadian islands and all of their impressive, modern coastal homes, in addition to the American Millionaire’s Row and Boldt Castle. Travelers on the American side (with valid passports) who do wish to explore Canada’s Thousand Islands region on foot can easily do so with several boat charters to Kingston (one of Canada’s former capitals), Brockville, and Gananoque- the region’s top ports on Lake Ontario.
5. World-Class Boating & Fishing
Considered by many as the freshwater boating capital of the world, fishing and boating activity is the main draw for most visitors. The Thousand Islands’ fine water quality attracts abundant marine life and is teeming with bass, northern pike, walleye and muskies- and is so clean that one can sometimes see yards below the sparkling surface. There is plenty of fishing gear rentals available for incoming travelers wanting to pack light, as well as innumerable private boat charters for any group size or occasion. The region also boasts prime freshwater wreck scuba diving sites, with scores of sunken ships and other watercraft immersed as deep as nearly two hundred feet below the St. Lawrence River.
6. Year-Round Outdoor Activities
The area’s versatile qualities make it an all-season haven for tourists who enjoy the outdoors. Summer months host fine warm weather for comfortable fishing, kayaking, and boating, as well as wine-tasting—Coyote Moon Vineyards is the region’s flagship winery in Clayton where guest can sample 19 varieties in both summer and winter months. Freezing winter temperatures don’t slow down Thousand Islands’ sporting activity one bit- powdered trails and roads become snowmobiling tracks in many areas of the region; the frozen St. Lawrence River attracts ice fishing; and many enjoy cross-country skiing in New York’s state parks and Canada’s coastline trails.