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An October weekend in Tarrytown, New York

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October is the perfect time to spend a weekend in Tarrytown, New York. If Tarrytown doesn’t ring a bell, perhaps the name Sleepy Hollow does. Washington Irving wrote “The Legend of Sleepy Hollow” about historical events that took place in Tarrytown during the Revolutionary War.  “The Legend of Sleepy Hollow” is big business  in October. There are readings of the famous story, haunted hay rides, tours of Irving’s home, and Sleepy Hollow cemetery tours. For more info click here.

October in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."Tarrytown is a town on the lower part of the Hudson River Valley and overlooks the Tappan Zee Bridge. It is accessible from NYC by Metro North.boys in hudson valley

To do:

Great Jack O’Lantern Blaze-

This regional favorite is worth however much travel time it takes you. This is the big reason October in Tarrytown is a must!

Van Cortland Manor is turned into a magical, extravagant Halloween wonderland. At last count 7,000 carved pumpkins twinkle in the darkness. The pumpkins are carved into zombies pushing their way out of the ground, butterflies, Celtic knots, and recently a merry-go-round. Jack O’Lanterns are formed into every possible formation and cartoon character your kids love.

.October in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."

October in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."

.October in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."

As you walk along the pathway, you will be delighted by the artistry. Please be aware that the ground is uneven so strollers aren’t a good idea. Plan on 1.5 hours


Kykuit is the home of John D. Rockefeller, the famous oil tycoon. It was built in the early 1900s and was the home of the Rockefellers for 4 generations before it became part of the national trust at the death of Nelson Rockefeller. This massive estate has daily tours offered of the house and the gardens.kykuit

This home is much less ostentatious than the vacation homes of Newport, Rhode Island. It was definitely built to be a family home and to accommodate each family member’s daily life and activities. My favorite room was the music room. I could envision myself sitting at the piano filling that spacious room with music.

But by far, my favorite part of the tour was the gardens! These gardens were designed to be enjoyed. Numerous terraces, pavilions, and many, many sculptures make for so many beautiful vistas. The kids loved running around after the tour and having so much open space to run.kykuit4kykuit2

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If you are traveling with kids, I would recommend the time-saver tour that lasts 1 ½ hours. The others are simply too long for most people let alone small ones.kykuit fountain

Plan on 2 hours


No fall trip would be complete without a visit to the home of Washington Irving, the author of “The Legend of Sleepy Hollow” and “Rip Van Winkle”. Although the house tour is great at any time of year, it’s nothing that would keep your child’s attention. But in October, they offer an afternoon shadow puppet show about the “Legend of Sleepy Hallow” along with scavenger hunts, and games.Sunnyside

For more info visit:

Plan on 2-3 hours.

Philipsburg Manor-

Philipsburg Manor is a very different home tour experience than either Kykuit or Sunnyside. Philipsburg was a mill and a farm, and although your tickets will get you a home tour, your kids will be delighted with the outdoor activities. If you go during the day, there are different hands-on exhibits for the kids to do. Cooking, weaving, milling, and more.phillipsburg hudson valleyOctober in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."

My boys particularly loved the cooking, where they helped to prepare an actual meal. There is a lot of room to run and play and lots to learn. Your kids will love every minute.October in Tarrytown is a great place for kids! There are many activities surrounding Halloween and "The Legend of Sleepy Hollow."October in Tarrytown, Phillipsburg manor cleaning yams

Marc Chagall and Henri Mattise windows-

If you can talk your kids into one more stop, this one is for the grown-ups. At Union Church of Pocantico Hills there are some of the most beautiful stained glass windows I have ever seen. This small church was built by John D. Rockefeller in 1921 right near the entrance to Kykuit. As your drive up to this tiny church, you would not be alone in thinking that this church could not be the repository of such illustrious works of art. But as you enter, and the light plays beautifully along the floor, you look up to see 10 masterpieces.

The Rose Window by Henri Matisse was commissioned by Nelson Rockefeller in 1954 and was Matisse’s last completed work.

The Chagall windows were commissioned by David Rockefeller and his descendants. They were commissioned one at a time and all tell the stories of the Old Testament. The most famous window pictures the parable of the Good Samaritan. Unlike Matisse’s more traditional stained glass, the Chagall windows were painted upon as opposed to colored glass being cut and fit together.

The price of admission is well worth the view.

Unfortunately, my images are blurry, but go here to see these beautiful windows.

Plan on 30 minutes

Good Eats:

Lefteris Gyro-

Do you have a favorite restaurant that isn’t anywhere close to where you live? This one is mine! I probably eat here 3-4 times a year, despite me living well over an hour away. I stop when we drive to visit family in Virginia, when we go to New Jersey, or when I really, really want good Greek food.greek saladsgreek 2

Although everything I have ever eaten here is great, I have to say the best thing here is the Greek salad topped with gyro meat or chicken. These things are huge and full of fresh, crispy veggies. And the salad dressing is the most amazing thing!! I could drink it!

Your kids will love their pita, fries, and souvlaki. You will love everything else!Tarrytown New York is only 30 minutes away from downtown Manhattan and is a wold away in feel. #tarrytown #fallweekend #autumnweekend

Sleepy Hollow, Ny is the home of the tale of the Headless Horseman. They celebrate Halloween with a month of family friendly scares! #tarrytown #halloween #newyorktravel



  1. September 22, 2018 / 10:31 pm

    It has been many years since I’ve traveled to this area. Looks like this was a great weekend. I’ll need to return there someday. I love Autumn in this part of the country. Your photo of the Greek salad with gyro meat is making me hungry. I love Greek food!

    • travelswiththecrew
      September 23, 2018 / 4:42 pm

      Autumn in New England is truly magical! I hope you can make it again soon.

  2. September 23, 2018 / 4:36 pm

    This looks like a lovely area! I have never seen pumpkin sculptures like that! A wonderful little town for kids and adults.
    Thank you, we will head there next time we are up that way.

    • travelswiththecrew
      September 23, 2018 / 4:42 pm

      You will love it. Thanks for the comment!

  3. Alexander Popkov
    September 23, 2018 / 7:14 pm

    These pumpkin art is really cool! Must take a lot of time to make it!

    • travelswiththecrew
      September 23, 2018 / 7:47 pm

      For the most part they are plastic pumpkins that they use year after year.

  4. September 23, 2018 / 7:20 pm

    The pumpkins at Jack O’Lantern blazs are really
    y creepy in all honest – and the gardens in Kykuit are something out of paradise!

    Great post by the way!

    Johnny | Johnny’s Traventures

  5. September 24, 2018 / 4:39 am

    Tarrytown looks fun place with lots of weekend activities. It also looks like a family place and also gardens with sculptures, beautiful flowers looks perfect.

  6. September 24, 2018 / 5:48 am

    Kykuit is indeed cute! Looks beautiful.Would love to visit New York someday.I have loads friends who reside there 🙂

  7. September 24, 2018 / 9:30 pm

    This looks like a really beautiful place where the entire family can relax during the weekend and do lots of activities together

  8. September 25, 2018 / 4:05 pm

    I had no idea of such a beautiful just so near to New York. I’d love to see all those halloween artistry, those look magical 😀 Thanks for sharing about a hidden gem 🙂

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