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.

 

Where is Tarrytown, New York?

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 train. It is a 30-minute ride from Grand Central.
• It is an hour by car from New Haven, Connecticut.

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.

Tickets are available starting at the end of September and going through November. Tickets are sold starting at the beginning of September and often get sold out by early October.

For tickets, click here.

You will walk through a predetermined path that weaves through incredible sculptures and works of pumpkin art. The entire Blaze experience lasts around 1 hour.  Please be aware that the ground is uneven, so strollers aren’t a good idea.

Plan on 1.5 hours

Kykuit

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.

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.

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.

 

Plan on 2 hours.

Sunnyside Estate

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, ” scavenger hunts, and games.

For more info visit: https://hudsonvalley.org/events/home-of-the-legend/

Plan on 2-3 hours.

Philipsburg Manor

Philipsburg Manor is a very different home tour experience than 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. My boys particularly loved the cooking, where they helped to prepare an actual meal. The costumed guides are great at involving the kids in their presentations.

There is a lot of room to run and play and lots to learn. Your kids will love every minute.

Marc Chagall and Henri Mattise’s windows

If you can talk your kids into one more stop, this one is for the grown-ups. Union Church of Pocantico Hills has 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.

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

The price of admission is well worth the view.

 

Plan on 30 minutes.

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.

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!

Where to stay in Tarrytown, New York

Tarrytown is a great place to stay if you are visiting the area. It is close to New York City without paying NYC prices, and it is right next to Route 287, which will get you to Connecticut or New Jersey quickly.

Tarrytown House Estate

This is my luxury pick if you are going to Tarrytown for a romantic or girl’s weekend. It is an exquisite hotel. The hotel is built on a hill overlooking the Hudson River and is particularly beautiful in the autumn. Enjoy their immaculate grounds and their gourmet restaurant.

Click here for reservations.

Courtyard by Marriott

This is my pick for families who are visiting. It is a great family hotel with big rooms and suites for families with more than 2 kids. The hotel is modern and chic and is in a very convenient location for exploring the area!

Click here for reservations.

 

Want to make a long weekend of your trip to Tarrytown? Check out this article to see local fall foliage as well.

For more day trips from NYC, check out this article.

Or visit the Berkshires for beautiful fall foliage.