“Everyday is Halloween, isn’t it? For some of us…“

– Tim Burton

Halloween is among us and you know I love this time of year! From spooky movies to all the fall decor – I am all in!

If you have seen the movie The Legend of Sleepy Hollow by Tim Burton or read the book by the famous Washington Irving, then you’re obviously in the right place. This fall I had the chance of visiting and exploring the real village of Sleepy Hollow in upstate New York. Although Sleepy Hollow is a wonder during the fall with lots of Halloween festivities to enjoy – it is great year-round. The movie/story has always been one of my favorites to enjoy during the fall so this was a real treat to get to see it in real life.

This past week we explored the infamous spooky Sleepy Hollow cemetery, Old Dutch Church, Headless Horseman bridge and Tarrytown which is the next town over! Best part of all it’s just a short drive from the city – making it the perfect little town to escape to.

Sleepy Hollow Cemetery & Headless Horseman Bridge

We started our exploring at the Sleepy Hollow Cemetery first! It seems a bit odd to explore a cemetery, believe me I know. However, it was so amazing and beautiful with the leaves changing everywhere I looked. It also seemed like it went on forever – it was deeper than we thought. Looking around and getting lost along the many pathways was exciting especially during the spooky season. We definitely found some creepy things too like a crypt with no name and even some odd stories inscribed on some of the headstones. Be sure to be on the lookout for Washington Irving’s (author of The Legend of Sleepy Hollow) burial site. Once you’re done there walk over to view the “headless horseman” bridge! During the Halloween season you can expect to see some festivals and the headless horseman roaming around! You can check out their seasonal events here.


After exploring the little village of Sleepy Hollow, we ended up in Tarrytown and found a beautiful castle hidden on top of a hill, The Castle. I found out that you can actually stay there and visit/tour the premises. It was a dream to find this little gem in the hills. If you have the chance to stay here let me know how it was! One day I hope to be back and stay there.

We ended the night with a lovely walk alongside the Westchester Riverwalk in Pierson Park. Bobby and I loved how we could see the NY skyline from the end of the Riverwalk and the lighthouse on the other. Tarrytown is located in the Hudson Valley and the Riverwalk is along the Hudson river so beautiful views are indeed everywhere. After walking the downtown, we had dinner at the Tarry Tavern and highly recommend it! I started with the seasonal butter squash soup and followed that up with a decadent truffle oil mac and cheese with crab crumbles. Lastly, I ended my meal with some yummy crème brûlée. Book your table here.

The Great Jack-O-Lantern Blaze

Last but not least, we saved THE BEST for last!!!!! We reserved tickets ahead of time for the Great Jack-O-Lantern Blaze just outside of Sleepy Hollow. It’s an amazing Halloween event of 7,000+ hand carved pumpkin displays across the farm. For safety masks were required during this time and everyone was compliant with the COVID-19 CDC guidelines. We had an absolute blast here and I was seriously blown away. I personally have never seen anything like it, so it truly was a spectacular night! Highly recommend putting this on your bucket list.

Sleepy Hollow Spark Notes Itinerary:

  • Sleepy Hollow Cemetery
  • Old Dutch Church
  • Headless Horseman Bridge
  • Halloween festivals *optional/seasonal
  • The Castle Hotel
  • Tarrytown Riverwalk & lighthouse
  • Downtown Tarrytown
  • Tarry Tavern for dinner
  • The Great Jack-O-Lantern Blaze

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That was our short little day in the Village of Sleepy Hollow and Tarrytown. It was the perfect little day trip of us. We had a great time and hope you get to enjoy and explore it too. Leave a comment if you’ve been or are planning to go soon!

As always,
Love Nickole