Westchester County: Visit New York State’s Golden Apple

Kykuit, home of the Rockefellers

A Seekender goes local in her own backyard, Westchester County, and describes five of her favorite places.

As part of the Hampton by Hilton #Seekender team, Jerry and I love to make the most of our weekends. Although we enjoy discovering and exploring new places and traveling afar, we are currently taking a (hopefully) short hiatus from overseas and cross-country jaunts as we sell our home and get ready to move.

We are very fortunate to live in an area of the country where the possibilities for digging deep into history, enjoying farm-to-table cuisine from the surrounding Hudson Valley, and taking advantage of beautiful scenery and the great outdoors are boundless—right in our own backyard. It’s a place where we can create a staycation at home!

Each of the four seasons in Westchester County is distinct with its own unique beauty, whether its fall foliage, flowering trees in spring, snowy landscapes or the sun and water sports of summer. We love entertaining visitors and introducing them to these riches.

If you are visiting New York City for business or pleasure, we highly recommend you spend some time following in our footsteps. Although native New Yorkers call it “Upstate” (which really is inaccurate when you look at the map), you may not realize that Westchester County is less than one hour from the city. It’s easily accessible by car, train or even on a boat along the majestic Hudson River, which forms the county’s western border. It’s a wonderful respite from the concrete and hectic energy of Manhattan.

Here are some of our top picks for things to see and do in leafy, serene Westchester County, which has been dubbed New York State’s “Golden Apple:”

1) Visit Kykuit

This living museum in Pocantico Hills, New York, was once the summer home of John D. Rockefeller, Sr. (founder of Standard Oil). Kykuit has been inhabited by several generations of the Rockefeller family, including Nelson D. Rockefeller, a New York State Governor and U.S. Vice-President. Each generation of the family has left its own mark on this historic house preserving and adding to both its stunning interior and to the beautifully landscaped grounds that sit on a hill overlooking the Hudson River.

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The metal garden sculptures are works of art but especially noteworthy is the collection of contemporary art housed in a basement gallery in the house. Nelson D. was once the chairman of the Museum of Modern Art, which was founded by his mother Abby. His modern art collection showcases the works of Alexander Calder, Andy Warhol, David Smith and others.

2) Explore Sunnyside

Set on the banks of the Hudson River in the village of Tarrytown, New York, Sunnyside was the home of Washington Irving, the author best known for “The Legend of Sleepy Hollow” and “Rip Van Winkle.” An example of Dutch Colonial Revival architecture, the original cottage in which Irving lived dates back to the 1690’s and still contains many of the writer’s original mid-19th century furnishings. The grounds and views are breathtaking.

Washington Irving's Sunnyside (Photo credit: Historic Hudson Valley)
Washington Irving’s Sunnyside (Photo credit: Historic Hudson Valley)

The house is set off a winding path lined with flowering trees, bushes, vines and water views that seem to wrap around the house. Now operated as a museum, Sunnyside is on the U.S. National Register of Historic Places and was was designated a U.S. National Historic Landmark in 1962. Be sure to also walk through the quaint downtown of Tarrytown with its Victorian houses, antique shops, and picturesque building facades, including the historic Queen Anne-style Tarrytown Music Hall, which opened in 1885. You might even be able to snag tickets for a concert performance.

Tarrytown Music Hall with its ornate roof and marquee
Tarrytown Music Hall with its ornate roof and marquee (Photo credit: Wikipedia)
Victorian House in Tarrytown, New York
Victorian House in Tarrytown, New York (Photo credit: More Time To Travel)

3) Meander through Sleepy Hollow Cemetery

In nearby Sleepy Hollow (in what used to be called North Tarrytown), New York, Sleepy Hollow Cemetery is an example of the rural cemetery movement, also called “garden cemeteries” because they were designed to be park-like. Behind a modest iron gate—amidst the crowded gravesites of his family members—is the simple marble gravestone of Washington Irving. The only reason it stands out from the rest is because it is routinely kept clean and polished through the cemetery’s historic preservation efforts.

Washington Irving's Grave at Sleepy Hollow Cemetery
Washington Irving’s Grave at Sleepy Hollow Cemetery
One of the stained glass windows on the Helmsley Mausoleum at Sleepy Hollow Cemetery
One of the stained glass windows on the Helmsley Mausoleum at Sleepy Hollow Cemetery

Other notables buried in this unique “local” cemetery include business icons and philanthropists with ties to Westchester County like Andrew Carnegie, Walter Chrysler, William Rockefeller, Elizabeth Arden and Brooke Astor. The most infamous and controversial burial site in the cemetery probably belongs to Leona (Queen of Mean) and her husband, Harry Helmsley. Stained glass windows on three sides of the mausoleum depict scenes of the New York City skyline. Another site not to be missed is the family gravesite of Daniel Delavan, a general in the Revolutionary War. Especially in winter, this perch offers spectacular views of the Tappan Zee Bridge, Hudson River, and New York City in the distance. 

4) Take a hike at Rockefeller State Park Preserve

Rockefeller State Park Preserve, located in Sleepy Hollow, New York was made possible by the generosity of its namesake family, a contribution in keeping with the Rockefeller’s extraordinary commitment to the preservation of open spaces. Initially, the family gifted more than 800 acres of property to New York State; with subsequent bequests, the park encompasses 1400 acres.

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The park includes a system of vintage carriage roads built by John D. Rockefeller, now accessible to visitors. Depending on the season, visitors can hike, run, fish (with a license), picnic, or go horseback riding. During winter, visitors can go sledding, snowshoeing, and cross-country skiing. With 180 recorded species, the park has been designated an IBA (Important Bird Area) by the National Audubon Society. Not surprisingly, the beauty of this park attracts many artists, including photographers and painters, whose work is often displayed in the gallery on premises.

5) Dine at Blue Hill at Stone Barns 

In addition to other accolades (including making the Pellegrino list of the World’s 50 Best Restaurants), Eater recently named Blue Hill at Stone Barns the “Best Restaurant in America.” Calling it a “restaurant” minimizes the significance of Blue Hill to the food world. Its chef and co-owner, Dan Barber, is nothing less than a culinary visionary. Set on 22 sprawling acres, Blue Hill is a farm and agricultural education center. The restaurant’s dining room (a beautifully renovated barn) is a theater of creativity and whimsy.

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There are no menus and, in fact, no two tables are served the exact same meal. What is consistent is that everything that comes out of the kitchen is fresh and sustainable; seasonally-driven; and sourced from this farm or others in the surrounding Hudson Valley. Although the restaurant is located on a two-lane country road, Blue Hill has become a world-class dining destination so it’s tough to get reservations. Plan ahead!


For more information about the broad range of attractions in Westchester County, see:

Hampton by Hilton logo
Hampton by Hilton logo

If you are visiting New York City and planning a Seekender weekend of your own in Westchester, all the attractions above are convenient to the The Hampton by Hilton property located on Route 119 in Tarrytown.

A welcome escape from the bustling city, the hotel offers a complimentary shuttle service to tourist attractions within a four-mile radius of the property.

Also worth visiting:

  • Historic Philipsburg Manor, a 17th century manor house that tells the history of slavery in the North;
  • Lyndhurst, a Gothic Revival country house that is part of the National Historic Trust
  • Union Church of Pocantico Hills, with its Chagall and Matisse stained glass windows
  • The Castle Hotel & Spa, a once private residence that is now a luxury hotel and spa set on a cliff overlooking the Hudson River. Brunch at the hotel’s Equus Restaurant is a special treat.
  • My hometown, Chappaqua, a “Presidential” hamlet in Westchester County 
Chappaqua in Winter (Photo credit: More Time To Travel)
Chappaqua in Winter (Photo credit: More Time To Travel)

Disclosure: As a member of the Seekender team, this post was sponsored by Hampton by Hilton but all opinions expressed in this post are my own.

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  1. Thx for this great post about Westchester Country, Irene. Visiting this amazing region was my first exposure to New York, and I think it is where I met you — at Troubeck! Would love to return sometime soon.

  2. I would love to do a road trip exactly like this, what a wonderful experience this would be for a spring or summer visit Irene.

  3. Wonderful article and great photographs! Just what we need at this time of year. It’s always so nice to explore all the intriguing and interesting nooks and crannies which we encounter on our travels. Just what the doctor ordered, so to speak! Thanks for this great post!

  4. I usually fly into NYC and therefore don’t venture out, but one day I’d like to drive down (from Toronto) towards Westchester. It would make a great road trip. There are so many interesting things to see including the Sleepy Hollow Cemetery. Would be neat to see so many “famous” people’s tombstones (Kind of like Pere Lachaise in Paris).

  5. Doug and I need to do this road trip! There was a time when our son was working on assignment in this area, and we kept saying we wanted to go visit> (Our son kept telling me that Eileen Fisher was headquartered there, to entice me.) But we never made it out to that part of New York. After seeing these photos now, and knowing you are there, we will try to make a plan. A fall trip in the “Sleepy Hollow” area would be a wonderful prelude to Halloween! Thanks for all the beautiful photos and tips.

  6. Chappaqua, isn’t that where Hillary lives? You guys live in such wonderful country! I would love to visit Sleepy Hollow Cemetery and anything to do with Washington Irving plus dine at that great farm/restaurant!

  7. Having never visited the US I am always interested when I see posts on different areas. This looks like one to add for when we do get there, lots of fascinating places to visit and the food looks amazing as well.

  8. I don’t think you’ll find any shortage of wonderful places to visit right in your own backyard of New York State. So much history and character to discover. I’m feeling the same sense of local discovery and enjoyment here in Scottsdale, our new hometown.

    Blue Hill sounds great — I love the idea of no two tables being served exactly the same meal. Fun!

  9. I once had the pleasure of visiting some of these Westchester Country properties as part of a boat excursion day trip from NYC. It was fabulous, but it seems they did discontinue it. It would definitely be worth renting a car and exploring on your own, and if I did that I would want to spend the night, too.

  10. Why travel afar when there’s so much to see and do so close to you in New York! (No, we understand the travel itch) And we can see from the photos why walking through Rockefeller Park is popular – it must be especially beautiful in summer when all the leaves are out :-).

  11. “Although native New Yorkers call [Westchester] ‘Upstate’ (which really is inaccurate when you look at the map), you may not realize that Westchester County is less than one hour from the city.”
    Funny. The author says that native New Yorkers are wrong calling Westchester part of ‘Upstate’; but the author doesn’t seem to know that New York City abuts Westchester County. Like it or not the Bronx is part of NYC.

    1. Touche! Yes, the Bronx is between Manhattan and Westchester. I was born in the Bronx:-)
      Just like New Yorkers call Westchester “upstate,” people often refer to Manhattan as “the city.”
      I stand corrected!

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