Fun in the Fall (Sleepy Hollow, New York)

Happy first day of fall (or autumn equinox)!

About four years ago my husband and I spent an October weekend in Sleepy Hollow, New York. We didn’t have any kids yet, but we had a blast acting like big kids. A fun in the fall Sleepy Hollow weekend is entertaining for anyone from age 1 to 100. However I don’t recommend bringing a stroller for the activities.

Our first activity was Sunnyside, one of Washington Irving’s former homes. Irving was the author of “The Legend of Sleeping Hollow“, making this a great place to start our fall, Halloween themed weekend. We took an interesting tour of the property and learned a little more about the man behind “Rip Van Winkle” and “The Legend of Sleeping Hollow” (also known as the headless horseman).

That evening we drove about 30 minutes to visit The Great Jake O’Lantern Blaze. We saw many parents and kids all having a really great time. Pumpkin carvings and sculptures covered every inch of the property. I was amazed by the work that must have gone into putting this event together. There were many little, winding paths and displays with more pumpkins and even music. I haven’t seen anything like it since that day.

The next day we went to Kykuit, the Rockefeller Estate. This part of the weekend was not halloween themed, but I’m so glad we toured the incredible Estate. And visiting this landmark in the fall was so stunning with all of the beautiful colors. The home itself is 100 years old and is a very well maintained time capsule. I recommend visiting the Hudson Valley, even if you only have time to tour the Rockefeller estate.

To end the weekend, we made a stop at the Sleepy Hollow Cemetery (adjacent to the Old Dutch Church). We saw where Washington Irving was buried and we met the headless horseman himself. It was the perfect way to end a short and very fun weekend in Sleep Hollow.

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