The name of the town Sleepy Hollow all started from a book by Washington Irving called “The Legend of Sleepy Hollow”. The book tells the story of the ghost of the Headless Horseman, a soldier who lost his head to a cannon ball during the Revolutionary War. Since Washington Irving and The Legend of Sleepy Hollow are so important, the town changed its name to North Tarrytown Sleepy Hollow in 1996.

This town reminds me of a smaller Salem, MA- same spooky energy. Perfect for a fall day out of the city!

GETTING AROUND

From NYC: You can take the train out of Grand Central for around an hour ride. and get off the stop Tarrytown.

THINGS TO DO

Stop One

Coffee Labs

Address: 7 Main St, Tarrytown, NY 10591

I had an iced latte with maple syrup and oat milk. It was the perfect fall drink to sip on while walking around. It does get a little crowded inside but the line moves quickly. The service is very good and if you have any questions about the menu the staff is friendly.

Stop two

Stroll down Main Road and Beekman Ave for cute shops and restaurants. My favorite ship was The Swan’s House- a home decor store with unique vintage and new items.

Stop three

Lunch at Horsefeathers

Address: 94 N Broadway Tarrytown, NY 10591

Worth the ambience alone, it's definitely a welcomed throwback to an old pub, and you can feel that it's been there forever, in a good way. Large menu, and lots of pumpkin beers! Prices range from $10-25 depending what you get.

Stop four

While heading toward Sleepy Hollow Cemetery, walk along New Broadway Street. The locals really know how to decorate for Halloween. They are all so festive and creative.

Stop five

Sleepy Hollow Cemetery

Address: 540 North Broadway, Sleepy Hollow, NY

The cemetery is about 90 acres where Washington Irving and the Rockfellers are buried in the cemetery. Walk or drive the grounds on your own or try an afternoon or evening guided tour. If I had more time I would have loved to do this to learn more about the beautiful art, architecture and cemetery symbolism. Day tours are $28 while the evening tours are $46.

Stop six

Philipsburg Manor

Address: 381 North Broadway, Sleepy Hollow, NY

In 1750, the manor was a working farm that relied on the labor of 23 slaves, making the Philipses one of the largest slaveholding families in the northern colonies. With a tour, you can learn how the enslaved community maintained family networks, shared their heritage and the work they were forced to do. Tickets are $15.

Stop seven

Headless Horseman Sculpture

Address: 362 North Broadway, Sleepy Hollow, NY

Spend a few minutes taking a photo of the Headless Horseman Sculpture. It’s a depiction of the moment in Irving’s book when the headless horseman throws the pumpkin at Ichabod Crane. It’s on Route 9 right across from the Philipsburg Manor.