Having done a few prior extended weekend mini vacations in the New York area, we were excited to embark upon another adventure visiting some additional historic homes along the Hudson as well as in the Connecticut and New York areas.
Day 1: Historic homes and a gourmet dinner
Washington Irving’s Sunnyside Estate
Nestled along the banks of the Hudson River, about an hour from LaGuardia, Washington Irving’s Sunnyside estate is a real gem. Known as the founding father of literature, Washington Irving created many well-known fictional characters authoring such classics as the Headless Horseman and Rip Van Winkle.
The Sunnyside estate began as a modest two-bedroom stone cottage that Irving purchased in 1835. He remodeled it and transformed it into the wonderful estate you can see today. He also added a pond and a waterfall on the grounds, but some paths were under renovation when we visited so we couldn’t get a good look at these. Irving lived out the last 25 years of his life in the estate and it’s here that he wrote many of his most famous works.
Today, touring the mansion is a fun experience. Each room has knowledgeable guides dressed up in epoch costumes. They explain the purpose of the rooms, the furniture, and tell some stories about events that took place at the estate. For example, the study still has Irving’s original desk as well as his original inkwell used to write many of his classics.
We enjoyed our tour, and you should plan to spend about an hour visiting the rooms and the grounds.
After Irving’s passing in 1859, John D. Rockefeller purchased the estate in 1945 transforming it into a national landmark and opening it to the public.
Lockwood Mathews Mansion
About an hour’s drive into Connecticut, the Lockwood Mathews Mansion is a beautiful (and huge) stone mansion nestled inside a park that was all part of the surrounding estate at one point.
The many signs around the estate describe the history of the remaining buildings as well as the troubled times of the family through the years. At one point, the city tried to demolish the estate to make way for a new city hall. It was local activists as well as the protective terms of the estate when it was bequeathed to the city that made it mandatory for the grounds to remain a park. The estate came close to demolition but fortunately was saved and is now a local gem.
Lockwood was born in 1812, and at 37 he became an early millionaire as a stockbroker on Wall Street. He was treasurer at a prominent railway and treasurer of the NY stock exchange.
In 1861 President Lincoln asked him to go to Europe to sell war bonds, where he is reported to have made over 600k in commissions the first year alone! By 1864 he was already the third most wealthy man in New York behind the Astors and the Vanderbilts.
However, Lockwood Mathews fell into financial trouble when gold tumbled due to market manipulation. After his passing his wife was unable to keep up with the mortgage payments and in 1941 the city of Norfolk bought the property opening it up to the public.
The 44,000 sq ft mansion took 150 men 4 years to build at a cost of over 2 million (the equivalent of about 40 million today). With 62 rooms, running hot and cold water, a historical burglar alarm system, heating and ventilation, the mansion was at the forefront of technology at the time. There are 12 toilets and 19 bedrooms, and we were impressed with the many sinks, some covered with what looked like a dresser that folded up to expose a sink below.
Modeled after a French château, construction was completed in 1868. The surrounding estate was also enormous at almost 39 acres and included a massive stable, a huge greenhouse, solarium, icehouse, chicken coop and more. Many of the building are now gone, but some have been converted and used for various modern purposes.
The original gate lodge was the first building on the site and was finished in 1865. It is now a radio station. The Lockwood family resided in it while the mansion was under construction. It too is made of cut granite and had polished hardwood floors and fresco secco walls. The property is now a national historic landmark.
We noticed some wear on the bottom of some of the wooden planks on the structure and after some investigation we were able to solve the mystery.
Many movies have been filmed at Lockwood including Dark Shadows, Harrigan’s Phone, and the popular Stepford Wives movies.
Be sure to check out all the spectacular woodwork on the door frames, banisters, and furniture. All made by the Herter brothers.
You can take a 1-hour tour or a 2-hour tour that also visits the bedrooms on the second floor. We took the longer tour as we wanted to see as much as we could but unlike the fabulous downstairs, the top floor was in dire need of restoration. All the same, it gave us the opportunity to see some unique aspects of the property. Either tour would be great to do. The mansion is only accessible with guided tours, and we would suggest you take a little extra time to explore the grounds as well.
Inn at Bellefield / Hyde Park
A new hotel, the Inn at Bellefield / Hyde Park, is where we stayed and then realized that it was situated in an historic area as well. The hotel is a Marriott-owned property that was built in 2024 and one we would highly recommend.
Literally right across the street from the Culinary Institute of America (CIA) it makes an ideal location to stay for visiting some of the historic homes along the Hudson River. And, of course, enjoy a meal or two at the CIA (but be sure to book your reservation weeks in advance as those restaurants do fill up).
The Bellefield site itself dates back to 1677 when a European family owned it. They sold it to James Rosevelt, great grandfather of President Franklin D. Rosevelt, in 1820. In the early 1900s it was a Jesuit farm, and in 1970 a portion of the land was sold to the Culinary Institute.
Culinary Institute of America: Bocuse Restaurant
We had once before explored this area and visited the Culinary Institute but without dinner reservations! While we managed to get a table at the American restaurant’s bar area at short notice for lunch, we learned that the fancier settings at their French and Italian restaurants sell out weeks in advance.
This time we booked early, reserving at the French restaurant Bocuse, and we were not disappointed. The restaurant, staffed by Culinary Institute students under the watchful eye of their professors did a wonderful job.
The meals themselves were spectacular. We had the duck and the slow-baked halibut. We both thought that this was the best halibut we had ever tasted. Perfectly cooked and flavorful the thick morsel of fish was placed on a bed of mashed potatoes with cauliflower, and a buttery cream sauce was poured on it at the table. It was hard to imagine any way to improve upon this dish.
Another highlight was the seasonal pumpkin chocolate fondant dessert that came rolled up in a paper-thin tube of dark chocolate. A work of art that also tasted delicious.
Day 2: Along the Hudson River
Walkway Over the Hudson
Next day, we headed out to an outdoor park area built upon an old railway bridge. Completed in 1889 at a cost of $3.5 million the Poughkeepsie-Highland Railroad Bridge was engineered to withstand gale force winds and the constant motion of the tidal river (the Hudson River flows both ways). Upon opening, the bridge was connected to a nationwide railway network bringing in coal, lumber, grain, and passengers across the Hudson into NY.
With the creation of the interstate highway and an increased reliance on trucking, railway traffic was decreasing and an unfortunate fire in 1974 damaged the Poughkeepsie side of the bridge rendering it inoperable.
By the 1980s the bridge was still unrepaired and abandoned. It was later transformed into a park in 1992 and more recently in 2009 it underwent a restoration program. When we were there on a Saturday morning, it was filled with cyclists of all ages along with runners and walkers.
You sure do get a great view from the 212-foot height of the Walkway Over the Hudson. It is actually the world’s longest elevated pedestrian bridge spanning 1.28 miles.
We enjoyed our walk across the span of the bridge and while the signage showed a walk through the village across the bridge, we opted to return crossing the span of the Hudson River a second time. A great way to get in some exercise along with some great views. There was also no admission fee to the bridge, but paid parking in the lot.
Bannerman Castle
Next, we headed into Beacon to take a boat ride to an abandoned island castle!
You must buy tickets online for the tour as there is no tour desk or office as such on site. The tour for the Bannerman Castle starts in the sleepy town of Beacon by the waterfront behind the train station. It is here that you board the tour boat to get to the island to see the historic Bannerman Castle.
We got there early but there was really not much to do. So, be sure to bring your own drinks and snacks. We spent our spare time walking around the parks enjoying the views. Much of the parking was reserved for permit holders and for the train but we found a few spots that were free for 4 hours and free all day on the weekend. Read the signs carefully, you don’t want to get towed.
The 30-minute boat ride on the Hudson River on the pontoon boat gives some great views of the Hudson Valley area and of the castle as you approach it!
The castle itself has been beaten by storms and unfortunately many of the walls have crumbled and fallen. A group of engineers put some retaining posts on two of the remaining partial walls to stop them from falling. That seems to be working but the whole area around the castle ruin is off limits and roped off for safety reasons.
The original castle was really more of a warehouse built in a whimsical castle-style. When operational, Bannerman would sell army surplus gear and had put up large banners to attract passing boats to attract them to come and buy supplies.
There isn’t much left today, and the 45-minute guided tour is really more to walk around some of the viewpoints with a guide who shows you historical pictures from a binder.
We got to explore what used to be a small lodge with a lovely view of the Hudson from the top of the hill. There, they have setup a small stage for shows and there was also a small snack bar with some t-shirts, cold water and some chips.
Even though you don’t really get to approach the castle ruin and you can tell the castle was built from concrete and brick (not made to last like the stone castles you see in Europe) it was still cool to see the vestiges of this historic site and to take the boat ride on the Hudson.
On the way back from our 2-hour tour we also passed a historical sailboat operated as a training vessel which was interesting to see. The students were hauling up the heavy sail with the captain shouting pull, pull, puuulll!
Day 3: Sleepy Hollow Area
We stayed at the Marriott Courtyard in Tarrytown. While adequate it was nothing much to write home about, but it was well situated. From here it was only a short drive to Sleepy Hollow and some of the historic mansions in the area such as Lyndhurst Mansion, Kykuit, Washington Irving’s Sunnyside Estate, and our favorite Armour-Stiner Octagon House.
Armour-Stiner Octagon House
Restored to its original 1870s appearance, the Armour-Stiner Octagonal House was at one point suffering structural degradation and was at the verge of collapse.
It was Manhattan financier Paul J. Armour that originally purchased the 2-acre lot in 1858 and built the whimsical octagonal house inspired by Orson Squire Fowler’s 1848 book A Home For All.
In 1872, Joseph Stiner, a New York City tea merchant purchased the house as a summer and weekend retreat buying more of the surrounding land to enhance the surrounding landscape. Stiner also added the two-story dome that comprises the third and fourth floors as well as the veranda around the first story.
In 1975, the home was sold to the National Trust for Historic Preservation to avoid destruction by a real estate developer. Later in 1976 the trust resold it into private ownership to Architect Joseph Pell Lombardi who has lovingly owned and restored the Armour-Stiner Octagon House since 1978.
It was a remarkable home, and we were happy to have visited it. It is the only fully domed octagonal house in the world!
Philipsburg Manor and Mill
In the town of Sleepy Hollow, you’ll find the Phillipsburg Manor and Mill. This is the area where you also take the tour bus to go visit Kykuit, the Rockefeller Estate on a separate ticket.
The Phillipsburg Manor is more like a historic village recreated to portray the day-to-day lives of the slaves that would have worked on the estate. At the time, the slaves were treated terribly working 10 hours a day or more for 6 days a week doing backbreaking work.
The staff today are dressed in vintage costumes and explain and demonstrate the many manual processes that were done at the time. The mill actually works, and we saw them grind corn into cornmeal with the huge 2,000-pound grind stones.
In another house we saw how the kitchen would have operated including the churning of butter. In a barn we saw how the slaves would separate the wheat from the chaff by beating it with a flail. There was even a medicinal exhibit with techniques from an old book from 1652.
Plan for at least an hour here to go through the various exhibits.
Sleepy Hollow Village
Unfortunately, the Sleepy Hollow Lighthouse was not accessible and the road to it was closed off. We believe it was under renovation but it looks like it would be worth a visit.
Just outside the cemetery the old Dutch Church is also a famous attraction. Built in 1685, the church is also the one that was featured in the Legend of Sleepy Hollow. The 3-acre burial ground next to it is the one that the Headless Horseman was based on.
While the church is no longer open for visitation you can walk around the tombstones in the cemetery and find some famous people, including Washington Irving, the author of the famous tales.
Kykuit, the Rockefeller Estate
Kykuit seems to be on top of the world as you take the shuttle bus up the hill from the Phillipsburg Manor where the tour begins. It was home to four generations of the Rockefeller family, beginning with the philanthropist John D. Rockefeller, founder of Standard Oil. Now the mansion is a historic site managed by the National Trust for Historic Preservation and is open to visitors for guided tours only.
In 1913 it cost over 29 million (almost a billion now) to build the beautiful mansion over 2 years. Believe it or not it cost even more (another 32 million) to complete the extensive gardens over the next 10 years.
You can do 1-, 2- and 3-hour tours and we opted for the longest tour. It can become overwhelming when viewing the many Picasso masterpieces and the hundreds of works of art throughout the site.
While there were no pictures allowed of the inside, even just what one could see outside in the gardens was amazing and we found ourselves snapping away.
The Boboli Gardens reproduction fountain in the front entranceway was carved in Italy and came in crates weighing over 30 tons. As you go through the property, you become numb to being impressed with the Tiffany lights, Wedgwood inlays, and so much more. Antique pieces from ancient China and paintings from masters adorn the rooms.
One interesting fact about the property is that there is no ballroom or grand staircase. The Rockefellers were staunch Baptists and there was no drinking, dancing, or gambling allowed on the premises.
A beautiful open ceiling oculus was added to the living-room which gives it a wonderful feeling of grandeur.
The basement is made up of five art galleries and includes many Picasso originals.
In a separate Carriage House, you’ll find a collection of horse carriages and antique cars.
Conclusion
Visiting some of the historic homes in the Hudson Valley area was a fun way to spend a long weekend. On a prior trip we had visited the Lyndhurst Mansion which is right next door to the Washington Irving’s Sunnyside Estate and would be a nice add-on to this itinerary.
See our post: A Sampling of Historic Homes and Mansions in the New York Area
Just keep in mind that to visit these mansions you must pre-book a guided tour and this requires some planning to see more than one mansion a day. Most tours were full, and we were glad we had booked ahead to see these gems.