Backstory: Montauk Shores Condominium & Teddy Roosevelt's Rough Riders

The Montauk Shores Condominium, a property at Ditch Plains, was originally a tent camp founded in 1898. At that time, it was home away from home for Colonel Teddy Roosevelt’s 1,020 Rough Riders, a cavalry unit that charged up San Juan Hill in Cuba during the Spanish American War and was now in Montauk with the rest of the US Army recuperating the summer after that effort.

About 200 military tents were pitched for the Rough Riders in Ditch Plains. General Wheeler’s HQ tent was also here. The rest of the army, 32,000 soldiers, had tents throughout the rolling hills of Montauk.

There’s a famous photograph of President McKinley visiting Roosevelt at a table set up in front of the Colonel’s tent back then. Roosevelt was a hero in that war. McKinley, two years later, chose Roosevelt as his running mate for his second term. And when McKinley was shot by an anarchist in Buffalo, Roosevelt became our president.

During World War II, the army had an encampment at this beach and built several structures on it. And afterwards, for a long time, the tent camp property was owned by a family who rented out sites by the weekend or month to visitors, mostly fishermen and their wives and children. A night at the site went for about $5. But in 1975, the owners of the property filed for bankruptcy, and it was brought out of bankruptcy by a group of 152 former renters, each of whom took ownership of a site. Together, this became Montauk Shores, the first condominium-owned tent camp in the State of New York. Soon, people put trailers on their sites, in accordance with what the condominium would allow. And after that, as a community, they built a children’s playground, and a swimming pool on the site. The families also made use of the buildings. Barbecues took place. Shuffleboard was played. Meetings were held. And of course, there was that 700 linear foot long oceanfront beach for the surfers and sunbathers.

When one of my sons, an active lifeguard and surfer, graduated college in 2003, I paid $52,000 for one of these trailer properties and put it in his name. He lived there year-around for a time – lots of fishermen and surfers in other trailers did – and in 2010 he bought a home in Springs and soon started a family. He sold the trailer for $80,000. Seemed like a good profit.

But then an astonishing thing happened. Around 2015, with a manned gate installed at the entrance of the community to provide privacy, the price for individual sites began to rise dramatically. They had been discovered by the rich. Soon many of these trailers, replaced by manufactured homes of the same size – about 800 square feet — were selling for hundreds of thousands of dollars. In recent years, some of them have sold for millions. Jimmy Buffett bid $700,000 for one but lost in 2018. The record price for one up front along the ocean went for $3.4 million.

The community of locals who bought earlier are astonished by this. They remain, still part of the now dwindling extended family of owners who bought low and stayed.

Many of them say they still love the camaraderie of the place, and the wealthy for the most part do not participate in it. Essentially, the wealthy keep to themselves.

“And we could sell,” a surfer recently told me, “and we’d have all this money but then we’d have to go and never come back. Right? But we love Montauk.”

It does seem to me there ought to be a marker at this beach to commemorate where Teddy Roosevelt and his Rough Riders lived for that long ago summer. We have the maps of where his campsite was. There are also books which describe all that went on there at that time.