My husband frequents the New York City area for business, and from time to time I like to fly up on points to join him for an extended weekend. Previously on these trips, we’ve had a lot of fun in New York City itself, and we’ve even broadened our horizons to Rhode Island, Hartford and New Jersey. We have also done some New York touring of historic Gilded Age mansions up in the Catskills and on Long Island. We had even stayed in a Gilded Age home turned hotel called the Mansion at Glen Cove.
On this trip we decided to explore more of Long Island going all the way to the Montauk Lighthouse at the very tip. We even splurged and treated ourselves to a luxurious stay in the historic Oheka Castle. It proved to be another weekend of fun.
During our extended weekend we visited the Sagamore Hill National Historic Site, the Vanderbilt Museum and Planetarium, both the Fire Island and Montauk lighthouses, the Long Island Maritime Museum, and the Oheka Castle where we stayed.
You can combine many of these Long Island activities into a day trip from New York City, a weekend, or even a full week or more. There is definitely a lot of places to visit and a lot to do. The décor also changes throughout the year. We did our Rhode Island trip around Halloween, which was fun, and still hope to visit some of the mansions closer to Christmas when they are decorated for the holidays.
Long Island’s Oyster Bay area
Sagamore Hill National Historic Site
Sagamore Hill as it’s known was Theodore Roosevelt’s home from 1885 through to his death in 1919. It’s located in Cove Neck on the north shore of Long Island near Oyster Bay.
The historic home is now a national park, and there is also a small museum housed in what was once his son’s home on the historic site. There are also many walking paths and remnants of the farm that was once there.
We had pre-booked a mansion tour and upon arrival there was just a small group (10 of us) queued up at the entrance of the historic home.
Sagamore Hill mansion tour
Run by the National Park Service you can only tour the historic Roosevelt home with reservations. The tour lasts about an hour at a cost of $15 ($1 for yearly or lifetime park pass holders). The site itself is open from sunrise to sunset Thursday through Sunday. There is ample free parking, and we would allocate about 2-3 hours to this site including the 1-hour tour.
I must admit that our first impression walking into the home was one of shock! Being avid hunters, the Roosevelts had decorated their summer home with all manner of hunting trophies, skins, and taxidermy mounts. Elephant tusks, rhino horns, skins of polar bears, lions, leopards, and cougars as well as many types of antelope heads adorned every wall and floor. We could not help but feel saddened by the macabre display of all these animals we love to see (alive and free).
Of course, the early 1900s was a different time, and as we discussed this with our guide, he explained that back then these ‘specimens’ were really the only way people ever got to see what these exotic animals looked like. There were no photo-safaris, no picture books, and no internet. The Smithsonian Institute had actually sponsored some of the specimen collecting safaris in order to discover new species. These animals were also not as endangered then as they are now.
All the same, coming face-to-face with a water buffalo head as we walked in through the front door certainly gave us a shock. Everywhere you looked, there were seemingly glass eyeballs looking back at you!
Noah, our guide went on to explain that Theodore Roosevelt was actually quite the conservationist and throughout his lifetime went on to establish many of the national parks and protected lands in the United States. He was able to protect over 230 million acres of nature reserves in the form of parks, sanctuaries, and national monuments.
This was despite the intense lobbying to turn these beautiful areas and refuges into tourist destinations by building casinos, hotels and fancy resorts.
President Roosevelt would have none of it. “Our people should see to it that they (these parks) are preserved for their children and their children’s children forever, with their majestic beauty all unmarred.”, he once said about Yosemite and Grand Teton.
He also went on to receive a Nobel Peace Prize for his efforts to avert the Russo-Japanese War. All this helped to warm our hearts towards the 26th president!
In the small museum, we also got to see his old pocket watch which interestingly enough had just been returned the day prior. They had held a ceremony with the National Park Service’s executives coming to present the artifact which had been lost for over 40 years. The stolen watch had turned up in an auction house where it was recognized by its engraving and finally returned to its rightful place where it could be seen by all. Nice!
During our tour we also learned that President Roosevelt used Sagamore Hill as the summer White House to avoid the heat and humidity of Washington.
Vanderbilt Museum and Planetarium
A little further east in Centerport Long Island, and only a short half hour drive away from Sagamore Hill, we visited the Vanderbilt Museum and Planetarium.
One of the smaller Vanderbilt homes, this beautiful museum, referred to as Eagle’s Nest was the summer home of the great-grandson of the late Cornelius Vanderbilt, William K. Vanderbilt II. The site is listed on the National Register of Historic Places.
Originally built in 1910, the cottage grew into a large (by most everyone else’s standards!) 24 room Spanish-Revival style mansion. It was purpose-built to be both a home as well as a museum to show off the many artifacts and specimens collected from the travels of the Vanderbilts.
The museum houses oceanic exhibits including specimens from the Galapagos, Asia, the Pacific Islands, Africa, and the Caribbean. Rare marine, bird and insect specimens are on display and many of these were the discoveries of new species at the time attributed to the Vanderbilts.
There was limited parking, and we were lucky when arriving in the afternoon to pull into a spot just as other guests were leaving. There was also a wedding taking place that afternoon so perhaps it was busier than usual.
As we bought our tickets, we were coaxed into getting a ticket to a planetarium show. In all honesty, while the planetarium was impressive and had a lot of amazing photographs of distant galaxies, the show itself was quite introductory and geared more towards children. With limited time we wish we would have had saved more time for the exhibits which all closed at 4pm.
There were numerous planetarium shows throughout the day so perhaps save that for last if you have limited time. They also sold tickets at the planetarium itself.
Eagle’s Nest mansion tour
We also purchased a mansion tour on arrival. These run on the hour with the last one also being at 4pm. So, after the planetarium we headed straight for the mansion for our tour of the historic home. This tour was superb, and our guide was animated and vibrant. She brought the whole era to life for us explaining the family history within the context of the period. This made touring the mansion a real pleasure. It also made us appreciate what a difference a great guide can make!
The Vanderbilts came to New York (then called New Amsterdam!) as poor immigrants from the Netherlands. Cornelius Vanderbilt started building his success as a ferry operator helping farmers bring produce to New York from New Jersey.
A keen businessman he built up the ferry business and later invested in the upcoming railroads including creating a direct line into NYC central station. The two huge eagles at the entrance of Eagle’s Nest are originals from Grand Central Station. You can’t miss them as you pull into the parking!
Being one of the ‘nouveau riche’ of the time, much of New York’s high society supposedly shunned the Vanderbilts and they were not invited to some of the most popular high class social parties.
One such example was a yearly ball for 400 held by Mrs. Alva which at the time really defined the who’s-who of NYC. To this, Mrs. Vanderbilt build a colossal mansion in Manhattan with a huge entertaining venue for 1,000 guests where she invited even more of the upper class to her lavish parties leaving out the Alvas. This of course eventually led to a truce. Just one of the many entertaining stories our wonderful guide bestowed upon us.
She also pointed out the fabricated Vanderbilt’s coat of arms on the fireplace in the kitchen. While they were not from nobility, Mrs. Vanderbilt had it made for her. Who was going to argue with her?
In its heyday the Vanderbilt Mansion at Eagle’s Nest property had 30-40 servants with about a dozen being overnighters. We toured the servants’ quarters and even they had water views. Pretty cool.
Throughout the mansion, there were so many exotic artifacts everywhere. Mr. Vanderbilt’s bed was an exact replica of Napoleon’s. His bathroom actually had what looked like a rain shower and the bedroom had recessed lights. Pretty innovative for the 1920s.
As part of the museum, there were also a couple of old cars. We were told by our guide that there were actually living quarters for the driver and the mechanic above the garage, to keep them handy at all times.
Do take the tour. We had a blast and I hope you get the same great guide we did.
Hall of Fishes – Marine Museum
Another highlight on the site was the Marine Museum which is in a separate building next to the parking lot. It houses displays of exotic fish and sea life from around the world. Don’t miss these, the collection is impressive.
We were told that many of the specimens were collected, and drawings had to be made so the fish could be later hand painted. This is because the skins would fade during transport, and they would lose the vibrant colors that William Vanderbilt saw when surveying and catching them.
The collection is extensive. In the house there is also a habitat wing with a full whale shark, an Egyptian mummy, and much, much, more.
Exploring the grounds at the Vanderbilt Museum
Aside from touring the house and the many exhibit halls, you can also walk around the beautiful grounds admiring the water views on the spectacular property.
You can also walk down to the boathouse built from an old historic mill. The 4-story boathouse is not open to the public but it’s a short walk down a paved road. There is also a seaplane hangar, but this was closed during our visit. There are over 40 acres of waterfront property as part of the estate.
A legacy
In his will, Vanderbilt made it clear that all of the property along with all its belongings should go to the public. Even the painting (which he supposedly hated) of a young William K. Vanderbilt II with his dog is hanging in the hallway.
We would allocate 3-4 hours to tour this property, especially if you want to take in a show at the planetarium. There was a drink vending machine, but we didn’t see any other concessions. The site closes at 5pm so best to go right after lunch.
Leaving Oyster Bay to get some Oysters
After a lot of walking, we had worked up a good appetite and headed out in search of some good oysters. Success! We ended up at Nicky’s on the Bay in Bayshore where we sampled some delicious local oysters. Even in late June the air had a chill to it, and we found ourselves shivering on the outside terrace. There was a vast metered parking lot (only $1/hr.) and lots of seating. They don’t take reservations. We would indeed recommend it!
Hyatt Regency Long Island
We stayed two nights at the centrally located Hyatt Regency Long Island. Even staying on points, we got a great room with a distant view of the bay. There was a Keurig coffee machine and a clean comfortable bed. The hotel itself was huge. They had 8 weddings going on, yes eight!
While there was really nothing within walking distance, we were a half hour from either coast and there was ample free parking. We would stay here again. Especially if we can get a free room on points :). Can’t beat the price! That said it was still a good 2 hours to get to Montauk with the traffic through the Hamptons.
See our post: Travel Tip: Are You Leaving Points on the Table?
Long Island Maritime Museum
This museum was definitely a hidden gem on our trip. Almost deserted, we enjoyed the beautiful collection of antique restored boats, a mock oyster house and more. Martha, one of the museums curators, was ever so friendly walking us through the exhibits and the stories behind them.
One display showed a lifesaving device used consisting of a cannon that would shoot a long line to a sinking ship close to the shoreline that had run up on a sand bar or on the rocks. This would essentially make a zipline for people to get to shore safely before the boat sank into the frigid waters. What looked like a pair of pants made into a barrel was used to ride down the line from the ships mast to shore!
The museum also had an interactive exhibit with a map of all the wrecks along Long Island. There were hundreds! There was also a scuba diving section describing some of the dives on these wrecks which of course we found interesting.
You can become a member of the museum which hosts a series of lectures as well as events including a seafood festival in August. There is also a Viking boat burning festival in October. You can buy tickets to sail on an 19th century schooner (a ride is included in the membership). We would definitely enjoy these if back in the area and would look to join should that happen.
Interestingly enough, we also saw the US sailing team on the grounds where they were launching their skiffs into the choppy seas to practice. We were impressed at the young team’s bravery heading into the rough seas during a small craft advisory. They did have a safety team in a rubber dinghy following them but all the same it was pretty choppy out there.
Montauk
Next, we headed out to the easternmost tip of Long Island, the historic town of Montauk.
The furthest point on Long Island, Montauk is a village at the east end of the Long Island Peninsula known for its beaches. It’s a popular getaway and travel destination for seaside activities, seafood restaurants, nature trails, and more. Montauk Point State Park is home to the national landmark, the historic Montauk Point Lighthouse.
Native Americans have lived on Long Island for over 4,000 years. The first white settlers were Dutch explorers in 1639. In the 1700s, Old Montauk Highway was constructed, and ranchers grazed cattle along the peninsula. It was in 1792 that President George Washington commissioned the construction of the lighthouse.
Carl Fisher, the developer of Miami Beach, had a dream to make Montauk the Miami Beach of the North. He laid out the town, built the golf course, the Manor, the Surf Club and the Yacht Club. He even put a casino on Star Island and opened up Lake Montauk to create a saltwater harbor. Unfortunately, his dreams faded out with the market crash of 1929.
Then, a hurricane in 1938 flooded the area. During WWII much of Montauk was turned into a naval base. Today, Montauk is indeed back to being a popular tourist destination and we sat in the weekend traffic long enough to attest to that!
Montauk Point Lighthouse
The historic Montauk Point Lighthouse and Museum is definitely worth a visit and exhibits a lot of the history about the area. Still a working lighthouse it is the 4th oldest working lighthouse in the United States.
There is a small two-story museum with history about the lighthouse, the lighthouse keepers, along with some artifacts from the times. You can climb the lighthouse steps but there was a long (1 hour) wait when we were there near the end of the afternoon. We kept thinking it would get shorter, but a last-minute rush made the line even longer and we contented ourselves with the already impressive views from the raised cliffs upon which the lighthouse is built.
In the museum we read that Montauk was also famous for the Amistad. This slave ship sailed from Cuba to the US in 1839 and the slaves basically took over the ship. While the Cuban government wanted to extradite them and bring them to be tried for treason, the locals and the US Supreme Court stood behind the slaves agreeing that they should be free.
We also met Tom, a veteran, at the lighthouse with an amazing talent for photography. He had taken whale and seal pictures all around Montauk. Even though we don’t have much room to put it up, we could not resist taking a picture from this talented photographer and we discussed his photos at length. Such a nice gentleman. We also took the trail down to the rocky shoreline where he has photographed some of the seals and whales he had on display. Some very impressive waves!
More oysters near Oyster Pond
After a day of touring and walking we were again on the lookout for more oysters. As we drove past the signs for Oyster Pond, we found Westlake Fish House at the West Lake Marina right next Lake Montauk. We had high expectations, and this place didn’t disappoint. We would recommend them highly. There was also a great band playing music from the 70s and 80s. Rock on!
On the way to Montauk, we had also stopped at the Lobster Roll Restaurant which is by the main road going through the Hamptons. This popular road stop was literally filled with cars and locals. Had to be good. And it was!
Fire Island
The next day we headed out to see the famous Fire Island Lighthouse. As we drove across the two bridges to get to Fire Island, we were immediately impressed with the tall brick water tower. This tower actually served as a beacon when they were rebuilding the new lighthouse.
There is plentiful parking in the Robert Mosses State Park where you can go to the beach or head to the Fire Island National Park which is where you’ll find the lighthouse. You can’t miss it!
We first headed to the beach which was impressively wide and seemed to go on forever. The beach spans almost 5 miles and attracts almost 4 million visitors yearly! On the day of our visit, it was extremely windy and the surf was rough. Even the lifeguards had setup a wind shelter on their raised perch with multiple umbrellas. Surprisingly we still saw some youngsters jumping into the huge 6-foot waves.
Entry to the state park costs $10, and the huge lot is the closest you can park to visit the lighthouse. The gravel road is only for the residents of Fire Island and requires a permit.
While only a 10–15-minute walk from the closest parking spots to the lighthouse we also found a pedicab that took us which saved us some wear and tear. We do love walking, but the rain clouds looked ominous, and we figured let’s get in while we can.
Fire Island Lighthouse
The lighthouse itself was built in 1858 and is 168 feet tall. Of the 25 lighthouses on Long Island, it’s actually the tallest. It was built in 1858 to replace the original 74 foot one built in 1826 whose remnants can still be seen next to the current one.
Arriving early, we were able to get tickets and climb the historic lighthouse tower and go outside on the raised balcony for panoramic views. Despite the cloudy day, the view from this height was impressive. So was the wind!! We had to hold our hats and glasses to make sure they didn’t fly off!
The park ranger atop the tower told us that one of the most popular days to come to climb the lighthouse is New Year’s Day! We couldn’t believe it and didn’t think we’d want to make the 15-minute walk from the parking never mind hang out in the wind atop the tower. New Yorkers are a tough bunch!
In the museum we discovered some of the history of Fire Island. In 1892 cholera broke out on a ship and the state purchased a hotel closed for the season to quarantine the passengers. Those living on the island objected and tried to stop the passengers from coming ashore. They still managed to disembark and stay at the hotel. Subsequently the state tried to lease the hotel to private enterprises, but the site was never very popular, I wonder why! The hotel was eventually torn down, and the area is all now part of Robert Moses State Park.
More oysters!
As you may have guessed, by now we were ready for more local seafood. We found a great local joint by the seashore called Kingston Clam Bar. Here we enjoyed locally caught clams and oysters along with more fresh seafood right on the dock.
After lunch we decided that we would head straight to our final stay and destination which was the Oheka Castle.
Oheka Castle
Built in 1919 by Otto Hermann Kahn on a huge 443-acre plot, the castle in Cold Spring Harbor is actually situated on the highest point in Long Island. But, this was not the case when Mr. Kahn bought the land. He had tried to purchase another spot before which was the actual highest point on Long Island. However, when this didn’t pan out, he brought in earth by horse and buggy to raise the land under Oheka Castle! Imagine!
Built as a French-style chateau it remains the second largest private residence ever built in America second only to the Biltmore Estate in the Blue Ridge Mountains that was built for the Vanderbilts.
The Kahn’s actually had five other homes before they built Oheka Castle for entertaining. It was constructed between 1917-1919 taking 2 years to build. The property now consists of 22 acres which remain from the original 433-acre estate. At the time, Mr. Kahn paid 1 million dollars for the lot, and everyone thought he was crazy. Imagine the value of this amount of land on Long Island now!
Addy Wolf and Otto were set up in an arranged marriage and had four kids, two girls and two boys. After having lost one of his previous homes to fire losing all their beautiful artwork, he wanted to build Oheka to be fireproof. The castle is made of concrete, stone and steel. It cost $11 million to build at the time (which would be approximately $200 million today). The 115,000 sq ft castle had 117 rooms, 50 bathrooms, and 39 fireplaces.
The home had just about everything one could imagine: a 10-car garage, an air strip, a deep dock for his 3 yachts, an 18-hole golf course (he was denied access to the country club because he was Jewish, so he made his own!), tennis courts, an indoor lap pool and more. At the time there was also a dairy farm. The name OHEKA comes from Otto HErman KAhn.
After Kahn’s death in 1934, the estate went through several uses including a retreat for NY sanitation workers and a military academy. It was then abandoned and fell into disrepair before the current developer Gary Melius purchased it and began restorations in 1984.
Researchers painstakingly went the distance to bring the castle to its former glory even sourcing materials for the slate roof from the very same quarry as the originals. Over 200 doors and windows were constructed and hand-crafted wrought iron was made to match the original railings fabricated by artisans.
Even the Formal Gardens were recreated using original drawings to reconstruct the many reflecting pools, sculptures, and fountains.
With over $40 million spent on the ongoing restoration, this is the largest such endeavor in American History. The castle is listed on the National Register of Historic Places as well as being a member of the historic hotels of America and historic hotels worldwide. You’ll also recognize the castle in notable films such as Citizen Kane, Royal Pains, and the series Succession, among others.
Oheka Castle mansion tour
We had a formal mansion tour given by Vicky who herself had been married at the castle 29 years prior. She did a great job answering questions and walking us through the castle pointing out features of the rooms, the restoration, and providing context and history.
This 1-hour tour was great, and many people only came for the tour (check their website for the schedule). No need to stay overnight to partake in this. After the tour, they also give full access to the various rooms in the castle for all participants whether stating at the castle or not. So, this would be a good of a way of exploring the castle without the expense of an overnight stay. Of course, spending the night in a castle is quite a treat so if you can indulge, why not!
With all this history, we opted to make the final day of our stay all about the castle. While it wasn’t inexpensive to spend the night, it was a special experience.
Oheka Castle stay
We had booked a deluxe room which had a distant view of the water on one side and a partial view of the gardens on the other. Pulling up through the impressive, crushed stone driveway past the row of 500 enormous evergreen hedge we ended up in the front cobblestone courtyard where the friendly valet Fernando swooped in to help with our luggage and parked our car. Valet parking is included in the rate.
We checked into our room and unpacked and went out to explore the grounds. On our first night most of the hotel was blocked off for a wedding party (which we are told can happen quite frequently).
That said, we made our escape and found a way into the gardens and the outside of the property to marvel at the views of the castle from the formal walled French Gardens complete with fountains and statues.
We must say that dinner was spectacular! While we sometimes take pictures it was so irresistible we forgot all about that as we dug in.
Angelina gave us 5-star service and everything we ordered was fantastic. We had the sea bass and the branzino fish, salad and appetizer. The chocolate flourless cake was amazing. On a funny note, and a funny conversation starter, we were brought the bill at the end along with a pen that said, ‘get your divorce paperwork’. Geez, what an end to a romantic dinner! We pointed this out to Angelina who laughed about it with us (and was probably happy we had a sense of humor). I guess they really need to get some castle pens instead of using random ones!
After dinner we headed back out to explore the grounds and were drawn to the fountains by a raucous that we first thought were birds in the hedges. As we got closer, we discovered that all that noise was actually coming from a large colony of tiny frogs barely an inch long. One of the other guests had picked one up and showed us. After having been in Costa Rica and hearing about the many small poisonous frogs there, we decided not to take any chances.
The next day we had breakfast which was setup in the original ballroom (They have built a new add-on wing which can seat 400 guests!). We enjoyed a large buffet sharing a table with some of the wedding party from the night before. They did have a couple of tables for two set up (perhaps for us) but they were occupied.
After our Oheka Castle mansion tour we also had a quick lunch at the OHK Restaurant. The owner of the castle, Gary, still lives on the premises, and was kind enough to come over and see us at lunch to say hello and to thank us for staying. That was really a nice touch.
Good to know:
- Check in is at 3pm and checkout at 11am.
- They suggest no jeans anywhere on the premises!
- The castle hotel is about an hour from LaGuardia depending on traffic.
- There were no coffee makers or mini bars in the rooms (not even the bridal suite which we got to see on our tour).
- While the bathroom faucets were quite elegant and in crystal, the design lacked the practicality of having any edges or anywhere to store your toiletries such as a traditional vanity.
- The decor and furniture were quite massive and in the style you might expect in a French chateau.
- Inside one of the cabinets, there was a small TV.
- There was nice marble edge around the bath but was quite high to get in or out of.
- The property also didn’t lend itself well to being accessible with the rough cobblestones and many steps.
It would be easy to include an in-room coffee machine or kettle and a mini fridge/minibar. We’ve grown accustomed to having these in the room, but perhaps they increase the risk of fire or ruining the furniture. That said, we have stayed in other renovated castles where the inside was completely modernized and new. From USB plugs to Nespresso machines to dimming lights and automatic shades.
The insides at the Oheka Castle while tasteful felt a bit dated. Another drawback was the lack of access to the various libraries and billiard rooms due to the wedding party the night we stayed (a Sunday). We did get to tour the mansion later in the evening and the next day.
Many of these converted mansions are really focused more on big ticket wedding venues. Some are strictly that but others that double as hotels also clearly give their priority to these larger and surely lucrative events. Perhaps staying on a weeknight would be the best bet to ensure access to all areas of the castle throughout one’s stay.
Conclusion
All in all, we enjoyed our extended weekend in Long Island and our castle stay at the Oheka. Of course, if you haven’t visited the Old Westbury House and Gardens, you really should. We had truly enjoyed our visit there on a prior trip.
We already have some other interesting trip ideas up our sleeve for another weekend getaway to the New York area. More to come on that front.