Castles, ruins, and lots of wine in NY's Thousand Islands

This trip is basically a real-life fairy tale.

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Created by Roadtrippers - July 27th 2018

Thousand Islands is an archipelago in the St. Lawrence River, which divides Upstate New York from Canada. It's a bit of a misnomer, since there are technically 1,864 islands in the river. Some are Canadian, and some are America, and all of them are gorgeous and boast their own unique histories. And, fun fact, there's an official definition as to what constitutes an island: "Emergent land within the river channel must have at least one square foot of land above water level year-round, and support at least two living trees."

In addition to being along a major shipping route and playing an important role in the War of 1812, Thousand Islands was a popular summer destination for wealthy industrialists during the early half of the 20th century. Its location made it ideal for rich vacationers from Cleveland, Chicago, Pittsburgh and, of course, New York City, and it was fashionable to have a property here. As a result, many millionaires of the time bought private islands to build huge summer retreats, many of which took the form of castles. There are two castles that you can still visit in the river today.

In addition to the opulent architecture, the whole area is loaded with amazing scenery, great conditions for growing wine, and vintage waterfront downtown districts with museums, shops, restaurants and more. It's a dreamy, fairy-tale-like destination that will transport you right back to the carefree summers of wealthy Victorians!

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Alexandria Bay, NY

Boldt Castle is one of the most famous attractions in all of the Thousand Islands. It's probably because the castle is striking, and it's got a memorable story to match. Built by George C. Boldt, wealthy proprietor of NYC's Waldorf Astoria, for his beloved wife Louise, the castle is on the appropriately named Heart Island. Construction on the grandiose Rhineland castle started in 1900. Plans for the building included 120 rooms on six stories, a bowling alley, plus tunnels, an arch, a pool, a power house, Italian gardens-- even a drawbridge, a dove cote and the Alster Tower (essentially a children's playroom). Overall, 300 workers were hired to construct Boldt's castle. No expense or detail was spared.

That is, until one day in 1904. Boldt suddenly ordered construction to be stopped. Louise had died unexpectedly, and Boldt couldn't imagine enjoying the castle without her. In fact, he never set foot on the island again. The almost-completed castle remained on the island, abandoned. For 73 years, it weathered storms, snow, and even vandals before the Thousand Islands Bridge Authority acquired the property in 1977. They made the decision to spruce the place up and open it to the public, so that everyone could enjoy it... even though Boldt never did. Millions of dollars have been put into restoring what was left and finishing what was left incomplete, and the results are jaw-dropping. Finished rooms have been furnished (mostly with modern pieces) and other rooms now house interpretive displays on the history of the island, the castle and the Boldt family.

Boat tour operators that can ferry curious visitors out to Heart Island include the Antique Boat Museum, Uncle Sam Boat Tours, and Clayton Island Tours.

Burrville Cider Mill

If you're visiting in the fall (read: between Labor Day and Thanksgiving), then you need to stop at the Burrville Cider Mill. The buildings are some of the oldest in the county, having been built on a 30-foot waterfall in 1801 as a grist and sawmill. It was owned by Capt. John Burr, for whom the town is named, for a bit in its early days. Burr was allegedly a pirate who would pilfer supply ships on Lake Ontario and turn a profit selling the stolen goods back to the troops in Sackets Harbor. Some even say his ghost still visits the mill.

But back to the cider. Visit in the morning on a Tuesday, Thursday, Saturday or Sunday to see them press freshly-picked New York apples into sweet cider. Or take a self-guided tour of the operation while you munch on a hot apple cider donut. The views of the waterfall and the fall foliage are not to be missed here!


Sackets Harbor, NY

Sackets Harbor played a major role in the War of 1812. Not only did two important battles occur near here, but the town played host to a shipyard, where 3,000 men worked building warships. Sackets Harbor itself was fortified and garrisoned with thousands of soldiers. Today, it's on the National Register of Historic Places. There's the restored Navy Yard and Commandant's House from the 1850s, and during the summer, a full recreation of an 1813 soldiers' camp is set up, complete with costumed interpreters. It's a fascinating look at an era that's often looked-over in history books... and you get some gorgeous views of the Thousand Islands area.

Singer Castle

The other famous castle that still stands in the Thousand Islands region is Singer Castle. Until recently, it had been known as the Dark Island Castle, after the island where it sits. It was built in the early 1900s for Frederick Gilbert Bourne, president of the Singer Manufacturing Company (hence the name 'Singer Castle'). It was designed by famed architect Ernest Flagg, and inspired by a castle in Woodstock, England that was described in Sir Walter Scott's book Woodstock.

Bourne died in 1919, and his daughter Marjorie took over (her brother tried to claim the property, but it ultimately went to Marjorie) and made some additions in the 1920s. When she died, the Roman Catholic Brothers of the Christian Schools got the property, and they sold it to the Harold Martin Evangelistic Association. During this time, the property started to fall into disrepair, and rumors about the real use of the property (which does contain a maze of secret passageways and hidden rooms) began to spread, adding an air of mystery to the castle on Dark Island.

Eventually, it was restored and opened for tours. One interesting fact about Singer Castle is that, though many other millionaires started to build castles on islands on the St. Lawrence River, this is the only one that was ever finished and lived in by its owner.

It's also got a lot of the stereotypical details a rich millionaire might add into a castle. This includes the medieval entranceway guarded by suits of armor; the walnut-paneled library, complete with a secret door opened by a switch hidden in a book and a framed portrait that tips back so anyone hiding inside the walls can spy on unknowing guests; tunnels that connect the various buildings on the island; and plenty of opulent decorations, including a working 5-story clock tower with four 6′ ft diameter clock faces that are rumored to be made of solid gold.

Cape Vincent, NY


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Hostelling isn't for everyone, but HI's Tibbetts Point Lighthouse location offers the chance to spend the night in a real historic lighthouse! It's fairly new, and you should be able to find a rooming option that meets your needs; plus you'll get to meet other travelers exploring the area and can make use of the kitchen if needed. Plus, it's next door to the Lighthouse Museum and only two miles from the town of Cape Vincent. It's one of the most unique places to stay in the area, so take advantage.

The Antique Boat Museum

You'll probably be spending at least some time during your trip to Thousand Islands in a boat (honestly, it'll probably be more than "some"). Pay tribute to the area's marine history at the Antique Boat Museum. With nearly 300 old-school boats on display, this is the premier freshwater nautical museum in the country. Learn all about canoes, rowboats, skiffs, speedboats, even steam-powered yachts. For added fun, take the 30-minute walking tour of La Duchesse, the mansion of a houseboat that hotelier George Boldt (more on him later) lived on during the summer. You can even attend a boat show or book a boat tour through the ABM!


Clayton, NY

Once an abandoned farm, the founders of Coyote Moon Vineyards have worked tirelessly to transform the property into one of the country's most innovative vineyards. They work with various universities to develop new ways to prune, trellis, and promote their delicious, hardy Northern Climate hybrid grapes. They make a wide variety of reds, whites, rosés, even fruit wines and meads with the grapes. A visit to their vineyard and tasting room location lets you sample 6 wines for only $4 (and for $1 extra, you can keep the souvenir glass). Enjoy the wine on their gorgeous patio, and once you're done, feel free to ask for a behind-the-scenes tour; the staff are more than willing to guide you around the property.

Thousand Islands Winery

Thousand Islands Winery is the largest farm winery in Northern New York, and they, too, grow Northern Climate hybrid grapes. The farm itself has a storied past; the house was built in 1881, the barn was ordered from a Sears & Roebuck catalogue in the 1920s, it was owned by a famed riverboat captain, it was a horse farm that raised Arabians... lots of history. But today, the winery is thriving. They make wines that they sort into several categories: Dry, Semi-Dry, Semi-Sweet, Sweet, and Fruit & Dessert Wines (they also make honeyed mead as well.) Take a tour of the property to get the lowdown on the history and to glimpse into their wine-making process, from growing and harvesting the grapes to bottling and tasting the finished product. Then head to the barn to sample their wares. They sell cheese, crackers, chocolates, and other snacks, along with wine by the glass or bottle. Sit in the barn loft or outside and enjoy a relaxing afternoon on the farm!

Lil River Fudge Co

To enhance those vintage Victorian vibes that mark the Thousand Islands region, pop into Lil River Fudge Co., an old-fashioned candy and ice cream shop. Retro candies and traditional homemade sweets like truffles, caramel corn, and taffy line the cases here, but the main attraction is, naturally, the fudge. It comes in a variety of flavors (like peanut butter and cookies and cream), all of which are mouth-wateringly delicious and melt-in-your-mouth creamy. They also serve Hershey's Ice Cream in cones, below massive sundaes, and mixed up into milkshakes. It's a one-stop shop for all things sweet!

The oldest historic waterfront building in the vintage downtown of Alexandria Bay is the Cornwall Brothers Store & Museum. Once serving as the town's general store, it opened in 1877 (11 years after the stone building was constructed). The Cornwall Brothers sold camp and island supplies, groceries, hardware, clothes, and assorted other general goods. Sadly, the business failed during the Great Depression, and the building housed a customs house, Coast Guard station and post office until the 1970s, when it was slated to be torn down. The local historical society stepped in to save it, though, and had it placed on the National Register of Historic Places. Today, it's an eclectic little museum that preserves the history of Alexandria Bay through interesting exhibits and displays. It's free to visit and is located near loads of other attractions downtown, so don't miss it!


Alexandria Bay, NY

Just Room Enough Island is the smallest habitable island in the US. It's a whopping 3,300 feet square (about one-thirteenth of an acre, for the record.) Most of that is taken up by a house, which was built by the Sizeland family in the 1950s, along with trees and shrubs and a beach. Miraculously, the house is still standing! Keep in mind that this is private property, so admire from the comfort of a boat and be respectful.

Mary Island State Park

End your trip by camping out on one of the islands. You'll have to catch a boat out to Mary Island State Park, but it's worth it to spend the night on the quiet, secluded patch of land in the river. The views into Canada from the island's rocky outcroppings are unmatched anywhere else on the river. Despite the fact that it's on an island, the campground is quite cozy, and the island features some dense woodland to further add to the remote and rustic atmosphere.

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Other islands of interest

Calumet Island once housed a castle as well, built by tobacco tycoon Charles G. Emery. It was comparatively modest, with 30 rooms, including a ballroom, a water tower, a lagoon for steam yachts, a guesthouse, a boathouse and an ice house. His second wife died at the castle, and afterwards, he locked the doors and abandoned it. It remained vacant until a fire destroyed most of the main building in 1956. You can still see some of the outbuildings, such as the water tower (which has been converted to a light house), ice house, power house, skiff house, servant's house, boat house, and even the staircase that led up to the castle. There was also once a castle on Pullman Island called Castle Rest that was owned by George M. Pullman (who designed the famous sleeper train cars); like Emery's castle, it was mostly demolished, though ancillary buildings still remain.

Deer Island is owned by Skull and Bones, the notorious Yale secret society. Members do attend retreats on the island, but it's hardly a lavish escape where wealthy members perform rituals; it's mostly "burned out stone buildings." But members visit it and have fond memories of it all the same!

Ironsides Island is a huge blue heron rookery that has been designated a National Natural Landmark.

And if you love exploring abandoned places, Carleton Island is home to the remains of the circa-1779 Fort Haldimand. It was built by the British during the American Revolution and was captured back by three Americans during the War of 1812.

Banner Photo Credit: Wikimedia Commons/Omegatron


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