Sleepy Hollow Travel Guide + Vacay Inspo

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At the risk of sounding extremely basic, I LOVE fall. This time of year is my favorite! So, to continue my annual mission to fill my fall to the brim with memories, I embarked on a trip to the infamous Sleepy Hollow.

Of course, I’ve been a fan of the tale since I was a kid and used to watch the Disney version. My interest in Washington Irving’s story was reinvigorated when the Sleepy Hollow film came out (classic Johnny Depp, hello!) and then again when I relocated to New York where it takes place.


The spooky little town of Sleepy Hollow did not disappoint, so I’m thrilled to share what I learned from my adventure! Read on for my tips and tricks before you plan your own trip…

When to go

Halloween, duh. Sleepy Hollow was affectionately nicknamed the “Halloween capital of the world” (although I’m sure there might be some folks in Salem and NoLa that disagree). Even if you aren’t big on the ghouls and goblins side of Halloween, fall is absolutely beautiful in the Hudson Valley area. So trust me on this, go in October. I took the New York Water Taxi’s Sleepy Hollow Ferry. The view from the Hudson River was breathtaking and the ride there was honestly one of the highlights of my trip! Even if you’re coming in from out of town, I think this is the route to go.

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What to wear
The most important piece is comfortable shoes! Nearly everything fun in Sleepy Hollow involves walking and exploring large, hilly areas (especially the cemetery, but more on that later). Leave your witchy heels at home, this is a job for Adidas. As far as your outfit, leggings and a flowy fall dress will do!

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What to eat

If you’re day tripping from Manhattan like I did, I recommend kicking off your Sleepy Hollow adventure with brunch at Ichabod’s, appropriately adjacent to the Headless Horseman bar on Irving Place in Manhattan. Don’t confuse this awesome spot with The Horseman in Sleepy Hollow. That Horseman is a sad diner and you will be disappointed if you eat there. Pro tip: Walk a little farther from Sleepy Hollow to Main Street in Tarrytown where you’ll find a string of foodie friendly restaurants (The Twisted Oak, yum) and hipster approved craft beer bars (The Oath, double yum). When you’re done, grab some homemade ice cream at Main Street Sweets. SO good.

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Where to stay

Planning to stay overnight? If you’re coming in from another area, The Castle Hotel and Spa should be your home away from home. This stunning resort is a hot spot for weddings and special events with good reason. The grounds are absolutely beautiful and have an eerie elegance, perfect for a Halloween vacay. If you’re an NYC dweller looking to save a few bucks, you can totally skip the overnight part and ferry back after a full day (it only takes about an hour to get back to the city).

 

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Where to play

It just would not be a trip to Sleepy Hollow if you skip the Headless Horseman bridge and take an obligatory tourist photo at the very spot where the horseman made his infamous ride and scared the bejeezus out of our friend Ichabod Crane. Also worth scoping out: Washington Irving’s Sunnyside where you can tour the grounds of Irving’s beautiful estate. Another not to be missed sight is The Great Jack O’Lantern Blaze, a walk-through pumpkin promenade at Van Courtlandt Manor with over 7,000 decorated jack o’lanterns on display. You also can’t miss the Old Dutch Church and Sleepy Hollow Cemetery (where many of New York’s elite have been laid to rest). Spooky, but beautiful.

Follow my advice and I promise you a perfect Halloween excursion to Sleepy Hollow! 👻👻👻

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