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Oyster Bay, NY - where history and money go hand-in-hand

Rolling estates flank the inlet leading into Oyster Bay in a way that can only make you wonder who the heck has this kind of money? Well, since you asked, let’s start with Billy Joel! At $37,500,000 - yep, that’s millions - not including the addition being added, this shoreline beauty is one of the many homes owned by Billy and his wife. At a more moderate price, the home to the west is estimated at 21 million and to the east a mere 13 million. Whew!

We wound our way past the shoreline opulence and pulled into the Oyster Bay Marine Center, and back into reality - at least for a little while. I asked the attendant servicing our boat to tell me about the highlights of Oyster Bay. He thought for a while and then in an uninterested tone said, “Well, aside from Billy’s house, it’s a do-nothing little town that’s only about four blocks long.” A bit disappointed in his response, we decided to hook-up to a mooring buoy for the evening and not go into town until the next day. 

I wanted to tour Sagamore Hill and the Oheka Castle in the morning, but quickly learned tickets were sold out to both places. Not giving up easily, I decided to call and was able to beg my way into a reservation at Sagamore Hill, but the castle was booked solid for two weeks. I asked the nice gentleman on the phone if we could walk the grounds without a tour; he said it was private property and not allowed. H o w e v e r...., “if you make a reservation at the castles restaurant through Open Table, you will gain access to the grounds. BINGO, I was on it!


We took an Uber to the castle where we were greeted at the front gate. After they confirmed our reservation, we drove down a long road surrounded by lush green grass and tall ornately trimmed hedges. We arrived to the back courtyard and made our way up the stairs to the restaurant while peeking into different rooms. The 1921 castle built by financier Otto Hermann Kahn was breathtaking.

Our table overlooked the courtyard where we watched guests arriving for a wedding. As the cars pulled up to the red carpet, trumpeters clothed in red uniforms of yesteryear announced their arrival. We were enjoying the parade when a man came up to our table and introduced himself as Gary, the owner. He was wearing an Oheka t-shirt and carrying a framed picture, so I secretly assumed he was really a maintenance worker and asked if he was hanging pictures today. "Nope, they keep hanging this picture up and I don't like it, so I keep taking it down" he said with a bit of frustration in his voice. He asked us where we were from and then told us about his favorite movies filmed in Seattle. We talked for ten minutes or so when his cell phone rang and he excused himself to take the call.

When our waiter returned with our appetizers, Tad asked if Gary was really the owner. "Yes, he is", he responded and went on to explain Gary bought the castle in 1984. It had been abandoned and fell into great disrepair. Gary started to restore the castle in 1988. He later sold it for 22 million, and when the new owner fell into hard times during the down-turn, Gary bought it back for 6 million. Images of how the castle looked when Gary initially purchased it line the halls of the lower level. You can read the full history here. The timeline is very cool!

Images of the Oheka Castle in disrepair

Images of the Oheka Castle today


Sagamore Hill, home to Teddy Roosevelt and referred to as the "Summer White House," from 1902-1906 was a Bully-good historic attraction! The museum located in The Orchard House on the lower end of the property was filled with historical artifacts that revealed the life of our 26th president.

The beautiful 23-room Victorian mansion estate now owned by the The National Park Service includes a 37-acre National Environmental Study Area of forest, tidal salt marsh and bay beach.

The story tells that when Teddy Roosevelt married his first wife, Alice Hathaway Lee, he was drawn back to Oyster Bay by fond childhood memories of family summers spent in the hamlet. Sadly, Alice died a few days after giving birth to their daughter and never saw the Queen-Anne sketches by Lamb and Rich Architects come to life.

In 1886 Teddy married Edith Kermit Carow, a friend of his sister whom he had known since a young boy. Together they would spend 30 years and raise six children in the home, until his death in 1919. Edith lived out her remaining life at Sagamore Hill, passing away in 1948 at the age of eighty-seven. Their first son, Ted built a home on the property known as The Old Orchard House.

The grounds are beautiful in a way only nature can create. Waiting for the house tour, Tad and I took pause on the large deck. I lavished in the thought of sitting in a rocker on the deck of Teddy Roosevelt's home and looking out to where he once found solace. The large tree next to the home was planted by Teddy in 1898 and died this past year. We were told it will be removed in the fall.

Photos are not allowed inside the home, but this short video is a historic recap of his marriage to Edith, his life, and has views of the inside of the home.

Contrary to the dock attendants description, we found the Town of Oyster Bay to be absolutely charming and only a short walk from the marina.

We met new friends, Jack and Caroline, from Middleburg, VA, who were moored near us. We enjoyed running into them and sharing coffee and stories!

We ended up spending two days here, but could have used another!

Marina Info:

Oyster Bay Marine Center (OBMC) was very nice. They have transient slips, but we chose to moor. The launch service was invaluable as we biked to Sagamore Hill and could load our bikes in their boat. In addition to the normal services such as fuel, the center offers mechanical repairs, detailing, wood working, and even sail rigging!


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