My trip to Upper Upstate New York and the Thousand Islands began in a small town called Oswego, right on the northeast corner of Lake Ontario. It’s known for its sunsets, believe it or not, and hopefully I’ll be able to show you a few examples in another post. I was privileged to a beautiful pink sky on my only night there, but because we were in the middle of dinner I did not get a chance to take many photos. There’s one example below, but I’m working on getting the rights to a few more – stay tuned.

The next morning we drove even further northeast along Lake Ontario, eventually reaching the St. Lawrence River and following it up to Alexandria Bay. A salty-dog town with a population of around 1,000 during the winter, the nice weather brings a stream of boaters and tourists to the area, raising the population to approximately 15,000.

No worries on feeling crowded as the town has the infastructure to support it – restaurants with boat parking, harbor activity, riverside lodging, and plenty of nightlife in the form of both live music and clubs. If you don’t rent a boat, tours leave the harbor throughout the day to cruise amongst the islands, and we caught a ride with Uncle Sam to two of the most well-known icons of the Seaway: Boldt Castle on Heart Island and Singer Castle on Dark Island.

Let’s start with Boldt Castle, a tragic story when you step back and look at it. Boldt worked his way up from dishwasher to hotel owner, made a bazillion dollars, and found the gal of his dreams. In 1900, he began building the mother of all Valentine’s Day gifts for that aforementioned woman, a 120-room castle upon a heart-shaped private island. One would assume that his entire self looked forward to the project’s completion, to the rest of his life with his wife.

But then the worst case scenario occurred for Mr. Boldt – his wife suddenly passed away, and the promised land fell right out from under his feet. Boldt immediately halted all construction on the island, leaving the unfinished castle behind as nothing more than a remembrance of his affection. It was deserted for about seventy years, minus the people who snuck in to party. On the top floors of the castle (which are still being renovated), you can see where hundreds of people had made note of their presence.

Most of the castle has been restored today based on information gathered about Boldt’s plans for the property. It’s beautiful, for sure, but perhaps the coolest aspect is walking around and thinking about the life that would have been lived had things gone according to plan. When I visited Hearst Castle in California, the phrase “if these walls could talk” often came to my mind, thinking about all the people and parties, the fun that must have took place. As I explored Boldt Island, a part of me felt sad knowing that what I was seeing was the result of a man’s dream that had come crashing down.

Singer Castle: It’s almost a tease touring these incredible properties, ropes and restrictions preventing full exploration. Singer Castle, built by the President of the Singer Sewing Machine Company, is one of the few that will let you stay the night in what they refer to as the “Royal Suite.”

It can sleep up to six people – $700 for the first two and $50-$60 a person thereafter. Seems expensive, but the sticker shock wears off when you divide $900 by six and realize that you’re staying in a four-story castle in the middle of the Thousand Islands Seaway.

Check out a few photos of these ridiculous estates. The power house on Heart Island is literally nicer than anything I’ll ever own, and to Mr. Boldt, it was only a power house.