In recent years, travelers have finally learned that there is more to the great state of New York beyond our buzzing city. One place in particular has been on a lot of globetrotters’ radar, and that place is Sleepy Hollow, New York.

Where to go for Vacation in October

If you are like me seeking where to go for vacation in October, Sleepy Hollow is THE place to be in September and October.  It embodies all of the things that we love about the fall – the things that, quite honestly, we could really use after the last two years of pandemonium. Cozy little restaurants, an abundance of nature (leaf peeping!), and good old-fashioned Halloween fun!

Plus, it’s only an hour past New York City, making it accessible for East Coasters and those already visiting the area.

If Sleepy Hollow has been on your radar, use this guide to plan your perfect trip there this fall.

Where is Sleepy Hollow?

Sleepy Hollow is a small village in the Hudson Valley area of New York State. It is so named because of the famous writer Washington Irving who lived in the area and wrote “The Legend of Sleepy Hollow.”

It’s important to note that Sleepy Hollow proper is actually quite small. The surrounding towns are only a few minutes away. They’re so close that you really won’t be able to tell where one begins and the next ends. Tarrytown, Elmsford, and Ossining are all suitable places to lodge and eat when visiting Sleepy Hollow.

Sleepy Hollow Experiences.

Now, let’s look at some of the best things to do in Sleepy Hollow, New York:

The Great Jack O’Lantern Blaze:

Perhaps the most sought-after experience in Sleepy Hollow is the Great Jack O’Lantern Blaze. While many cities are offering similar experiences, there’s something extra special about visiting the one in ‘Halloween Headquarters.’

Artists begin carving pumpkins in the summer and by October, THOUSANDS of them are lit and make their appearance for tons of spectators to enjoy. The level of intricate detail and craftsmanship is awe-inspiring. One of the most remarkable facets is how many pumpkins are used often to create one larger piece, such as a giant carousel, a re-creation of a famous art piece, or a cultural tapestry.

Grab tickets to this one early. It’s something that you’ll remember for a lifetime.

Sleepy Hollow Cemetery Tours:

Typically we might think of cemeteries as places that are uncomfortable. The cemetery in Sleepy Hollow is one of the most beautiful that I’ve ever seen. It’s truly akin to an outdoor art museum as many of the crypts, tombs, and headstones are so intricately crafted, unique, and impossibly precise. Be sure to walk around during the day to gain a real appreciation.

However, at night, it’s imperative to take a spooky walking tour through the cemetery. You’ll hear all about the incredible ways that people who now lay in its confines perished and left this world. The tour guides even give you an old-style lantern to carry around as you hear each of the tales.

Irving’s Legend:

The entire town of Sleepy Hollow exists largely because of “The Legend of Sleep Hollow.” It’s a horror story written by Washington Irving in the 19th century. It has since reached international fame, with the tale translated into a multitude of languages. Countless adaptations for the screen and stage having been created.

During Halloween season, watch one of the most gifted story tellers in the United States re-tell the beloved classic. He’ll leave you laughing, on the edge of your seat, and, of course, a little spooked.

Washington Irving’s Sunnyside Estate:

On a chilly fall day, there’s nothing more dreamy than touring the home and grounds of the infamous Washington Irving. Smiling attendants are usually selling warm cider and snacks for you to enjoy before or after your tour. Costumed docents walk you through the home. It’s fun to imagine the infamous American author, his family, and guests cozying up in the small rooms of the estate as the ghoulish wind whips by and the mighty river churns outside. Don’t forget to catch the finger puppet performance of “The Legend of Sleepy Hollow” while you’re there!

Tarrytown Music Hall Ghost Tours:

The music hall theater is over 130 years old, so you know that there’s bound to be some interesting history. You can learn all about what went on during all of those years inside of the theater. Plus, you’ll hear about its many secrets, and best of all, learn about the other-worldly spirits that still haunt the premises. Guests are led by Gotham teams who allow their groups to use special advanced technology to find paranormal spirits within the music hall. What’s extra-spooky about this attraction, however, is the price tag attached…$135 per person. But, it’s an amazing experience!

Sleepy Hollow Haunted Hayride:

This is another event that only takes place at the end of October. This year it’s on October 22nd and 23rd. The hay wagon takes guests down lively Main Street, past the Old Dutch Church, and into the spooky, dark woods of the hollow. The hayride retraces the path Ichabod Crane took as he tried to outrun the Headless Horseman.

Farmer’s Markets:

TaSH Farmer’s Market and the Irvington Farmer’s Markets are the two in town to visit. Both feature just about every yummy and beautiful natural product you can imagine, from cheese to wine to bread to fresh-cut flowers. Locally grown produce makes a wonderful souvenir that won’t take up room in your living space nor gather dust for years to come.

Hulda’s Night:

Everything here circles back to “The Legend of Sleepy Hollow.” In the story, the author mentions that the town was under the spell of a “high German doctor.” There are many who think that he’s alluding to a healer woman from Central Europe. She lived in Rockefeller State Park, and if you hike through Witch’s Spring Trail, you can walk by the area that used to be her dwelling.

In this experience, guests go to that same trail and hear all about her life and story. Drinks and snacks are given at the end of the storytelling. Unfortunately, this is another one limited to just a few days at the end of October. It’s October 27 through 30th with two shows per evening at 6:00PM and 7:00PM.

Halloween Parade: 

Each year, towards the end of October, the Village of Tarrytown hosts a Halloween parade. It starts by Patriot’s Park and heads down Main Street. Afterwards, there’s a giant block party with a DJ and performances. Most people choose to wear their costumes, so don’t be shy about wearing yours!

The parade is on October 23rd this year at 5:30PM.

Sleepy Hollow Film Festival:

This year, the Sleepy Hollow Film Festival is from October 15th through the 17th. On the Sleepy Hollow waterfront, a pop-up drive-in theater will show pieces submitted by contestants. I’ll be updating this as more information comes out!

Not Running for 2021.

The following experiences are unfortunately not running for the 2021 season, but I’ve included them for future visits to Sleepy Hollow.

Horseman’s Hollow:

This one is a ‘spooky walk’ or haunted house type experience. In front of the Philipsburg Manor is a re-created Sleepy Hollow village from the 1700s where everyone has ‘gone mad’ from the Headless Horseman. Costumed actors roam around and pop out to scare guests. There’s some serious talent in the construction of ‘haunted’ places like a chapel and spooky cabins.

Sleepy Hollow Experience:

If you’ve ever been to an immersive theater show, then you know how utterly and insanely captivating the performances can be. This immersive version of “The Legend of Sleepy Hollow” often sells out but it is not to be missed. Guests follow all of the characters from the story through every scene of the tale, and even get to hang out and have some treats at the grand Van Tassel harvest party.

Old Dutch Church Fest:

This event takes places on the grounds of the Old Dutch Church which is actually part of the setting of the Legend of Sleepy Hollow. Guests can buy sweets, ciders, beer, sausages, hot dogs, and souvenirs. Most proceeds go to the upkeep of the adjacent cemetery which houses graves of many folks, including patriots of the American Revolutionary War.

Nevermore:

If you’re familiar with Edgar Allan Poe, then you’ll at least remember hearing the phrase ‘nevermore.’ It comes from his chilling piece of writing entitled “The Raven.” Nevermore is a theatrical and aerial arts/circus-style adaptation of that Poe classic. Watch acrobats soar as they re-tell the story set to spooky music.

Not-So-Spooky Places to Visit in Sleepy Hollow.

And finally, here are some things to do in Sleepy Hollow, New York that aren’t so spooky:

Sleepy Hollow Lighthouse Tours: 

The Sleepy Hollow Lighthouse has been in use for eighty years and was rendered obsolete in the early sixties due to the Tappan Zee Bridge being built with navigational lights which serve the same purpose as the lighthouse. Learn about the dozen or so lighthouse keepers and their families when you take a tour.

The Octagon House: 

Few houses are more intriguing than the Armour-Stiner house. Built in the pre-Civil War period, its pink walls and unusual shape give the building a playful, antique, borderline spooky appearance. It’s modeled after the style of ancient temples and with such a storied history, it feels just as old. While you’re not able to visit and enter on your own, you can book a tour and learn all about the history of the house!

Kykuit:

If you’ve ever wondered how the other half lived, now is your chance. Kykuit was the home to four generations of Rockefeller family members. Thanks to the remaining descendants, guests have the opportunity to walk through the mansion and grounds on guided tours. You’ll truly be in awe as you see the modern amenities of the time that the family used inside their home as well as the many rooms (more than you’d even know what to do with) and their lavish aesthetic. Hearing stories about the family humanizes them a lot, as most people see them as celebrities. The house is furnished to look exactly as it would have when the original family members were living within its walls.

Old Dutch Church:

This church has a history that dates all the way back to the late 1600s. Its name comes from when the Dutch Merchant Company ruled New York before the British. Walk on the creaking floor boards, listen to the wind howl outside the fragile windows, and admire the centuries-old organ. Outside, you can explore the 2.5 acres of cemetery and rolling green land. The church is a focal point of Washington Irving’s classic, “The Legend of Sleepy Hollow.”

Union Church of Pocantico Hills:

This church really just fits the entire aesthetic of Sleepy Hollow. It has a rustic charm that fits right into the surrounding nature. It also has a bit of a storied history connecting directly to the Rockefeller family and Henri Matisse. There are usually events here such as book sales where you can find gently used novels for a dollar apiece.

Lyndhurst:

If you’re into castles that looked as though they’re plucked from the pages of a storybook, then you’ll really enjoy Lyndhurst. Built in the mid-1800s, it’s had a few ‘who’s who’ of owners, including Jay Gould, the railroad baron. Take a tour of the opulent inside, walk around the gardens, and partake in the many fairs that take place on the grounds.

Places to Stay in Sleepy Hollow.

To fully experience Sleepy Hollow, you’ll need to spend a few days there. I recommend booking your hotel well in advance if you plan to visit during the busy Halloween season!

Budget Option:

Don’t want to break the bank? No problem, book a stay at…

Days Inn:

We’ve snagged a room here for under $100 and enjoyed it very much. It’s no frills, but warm, cozy, and a fine place to watch Hocus Pocus after a cemetery walk or evening meal.

Moderate Options: 

If you want a few more amenities, consider one of these mis-range accommodations:

Comfort Inn and Suites:

Very clean, and extremely comfortable beds. The best part about staying here is the great amount of space that you’ll have. That’s especially important if you’re traveling with a family.

Courtyard Marriott:

A fireplace in the lobby and lots of space for relaxing, enjoying a quick breakfast, or getting some work done makes this a comfortable option. Guest rooms are clean, usually come with a desk, and offer just enough space (although not a ton of it).

Hampton Inn:

If you’ve stayed at a Hampton Inn, then you know. Clean and a decent amount of space. There are sundries for sale if you need some snacks or basic toiletries.

Luxury Options:

Finally, if you want to stay in style, check out one of these options:

Hotel Nyack:

If you’re into hotels with aesthetic appeal, this is the place for you. It’s industrial enough to feel as though it belongs somewhere in Brooklyn, yet offers balcony views of the Hudson River. The rooms feel extra luxurious with chandeliers, high-backed chairs, and wallpaper that gives serious ‘boudoir’ vibes.

Sleepy Hollow Hotel & Conference Center:

Roaring stone fireplaces, high wooden beamed ceilings, and dark cherry stained features make this place feel like it belongs in Sleepy Hollow. Cool amenities include a gorgeous indoor pool and gym. The rooms are oh-so-spacious and full of warm, autumn colors.

Tarrytown House Estate:

This estate boasts over 200 guest rooms and 10 Georgian style rooms. The ambiance is minimalist meets artistic, and the pale colors and bursts of white make it feel sparkling clean. The King House Mansion which houses some of the rooms was constructed in 1840. There’s a basketball court, horseshoe court, tennis court, indoor and outdoor pools, a restaurant, and a fitness center.

Castle Hotel and Spa:

This place is quite literally a castle. It’s decorated with cozy fireplaces, luxurious comforters on four-poster beds, and candelabras hanging from the ceilings. With sweeping views of the New York City skyline, Hudson River, and Palisades, this makes it an extra luxurious option for lodging.

Places to Eat in Sleepy Hollow.

Of course, no travel guide would be complete without discussing local food options!

Pik Nik BBQ:

My personal favorite spot for lunch! It’s a full sensory experience with perhaps the best playlist ever created, the smell of smoked meats wafting through the air, and the taste of slow roasted pork, creamy mac and cheese, and tangy apple coleslaw. Ribs, chicken, andouille sausage, burnt ends, cornbread, potato salad, everything barbecue classic is available for your gastronomic pleasure. Be aware that space can be limited.

Lefteris Gyro:

Another exceedingly popular spot that has limited seating, but at least it’s both indoor and outdoor. I love this place, and from experience I can say that you need to order enough food so that you can literally roll out when you’re done. The shrimp saganaki is potent, pungent, and bursting with flavor — personally I’d choose it every time. If shrimp isn’t your thing, don’t worry, there’s what feels like dozens of other options, much more than your typical Greek restaurant. The avgolemono soup (lemon chicken) warms both the bones and the soul. It’s a nice light option. Have a glass of wine with dinner and a Greek frappe or coffee (careful there) for after your meal.

Goosefeather: 

This restaurant has both indoor and outdoor seating and is a MUST if you’re looking for savory, decadent, comfort food. The menu is Hong Kong inspired and you’ll want to order the shaved snow peas, sweet summer corn, and Cantonese roast duck, in addition to the delicious dim sum offerings. For dessert? Mochi waffles, of course.

Horsefeathers:

Dimly lit, warmly inviting, and Halloween-esque, this is a MUST visit in Sleepy Hollow. Cider, beer, and adult juice boxes are the name of the game in terms of booze. For sustenance, you can visit for brunch, lunch, or dinner. The menu feels endless (there are over a hundred items) and includes lots of options by way of pasta, meat and poultry, seafood, burgers and sandwiches, and salads. When dessert rolls around, opt for a boozy coffee — there are seven versions to choose from!

Guadalajara:

Make reservations in advance, because this popular Mexican eatery is packed nearly every night in October. Whatever you order, rest assured that it will be awesome. In my humble opinion, you have to start your meal off with the guacamole prepared table-side and the queso fundido (the best I’ve ever had). The tortilla soup is a heavenly second course and although you’ll be full, make room for an entree — it’s worth it. Margaritas pack a punch here and come in a variety of flavors.

Visiting during October is extra special because every staff member dresses up in costume complete with elaborate make up!

Sweetgrass Grill:

The food at this light, airy beach restaurant is seasonal and locally sourced from farms nearby. For brunch try the lemon blueberry waffle or the heirloom tomato hash (yum!). Salads and sandwiches make up the majority of the menu which makes this a great lunch spot (even for takeout).

Tarry Tavern:

Situated right on Main Street, this place isn’t a bad choice at all for a lunch with some upscale options. Picture a place that serves comfort food, and then levels up that comfort food — like mac and cheese with crab meat and white truffle, for instance. Pork cheeks, sea scallops, burrata cheese, duck confit fettuccine, and Amish roasted half-chickens are just a fraction of the elevated comfort food that makes up this menu.

J.P. Doyle’s:

A beer garden meets Irish tavern that has all of the classics – burgers, Reubens, potato skins, and more. Don’t miss their brunch or taco Tuesday specials – that one comes served with a side of trivia!

Bridge View Tavern:

Despite being a ‘tavern,’ the fare goes way beyond buffalo wings and mozzarella sticks. Try options like fig and goat cheese flat bread, curry vegetables, a wild boar chorizo burger, or elk burger. This is by no means an exhaustive list of entrees, but as you can see, the menu is anything by typical. Of course you’ll want to get a beer, cider, or mixed drink, such as a grapefruit martini, to wash it all down.

Hudson Farmer and the Fish:

Hudson Farmer and the Fish sits on the Hudson’s riverbank and featured a seasonal menu. Unsurprisingly given the restaurant’s name, there’s a heavy focus on locally sourced seafood – both raw and cooked. There’s also a pizza menu selection that will have you saying, “well…what’s the harm in ordering ALL of them?” Good luck deciding between options like the Clam (clams, bacon, celery, onion, thyme, garlic, fontina and parmesan) or the Mushroom (truffle, arugula, fontina, and portobello mushrooms).

Hudson Anchor Seafood and Grill:

Looking for a meal with a gorgeous view? You’ve found the right place. The menu has some more ‘mature’ offerings like panzanella salad, paella, and seafood risotto, but by no means is the atmosphere stuffy. String lights, wide umbrellas, and decorative fall touches like hay bales and corn stalks give this place an intimate, laid-back vibe.

Coffee and Such in Sleepy Hollow.

If you just need a cup of coffee and a snack, head to one of these local gems:

Coffee Lab Roasters:

An absolute favorite among locals and visitors alike, maybe because it’s puppy themed?! Enjoy knock out coffee and pastry options like almond or chocolate croissants, Scottish short bread, and cake pops. They offer unique and healthy coffee options like CBD vanilla and golden turmeric.

Muddy Water Coffee & Cafe:

Whether you want a cozy meal, sweet pastry, or just a coffee pick-me-up — this is a great spot for something quick and something that is made with love and care!

Places to Drink in Sleepy Hollow.

And finally, you’ll likely want to check out some of the area’s breweries after a long day of exploring!

Sing Sing Kill Brewery:

Looking for a brewery that doesn’t frown on bringing your kids along? Visit Sing Sing! Enjoy decadent options like Cherry Chocolate Milk Stout or Killer Cream Ale and get some hot dogs and soft baked pretzels to go with your brews.

Speaking of kids, here’s what you need to know if you’ll be visiting Sleepy Hollow with little ones.

Beekman Ale House:

Beekman Ale House knows that the people love Halloween! Throughout the month of October, Beekman’s celebrates Pumpkin Fest with a series of rotating beers on tap that are all pumpkin flavored. When you’re getting good and buzzed, order any of the five twelve-inch pies on the menu (hot oil flavor is a good choice) or classic apps like mozzarella triangles and wings. The wooden interior and neighborhood vibe give this bar a cozy, fun ambiance.

Captain Lawrence Brewing Company:

As far as craft beers go, Captain Lawrence is becoming increasingly popular. With flavors like Autumn Blaze Pumpkin Ale, Golden Delicious Tripel, and a host of IPAs and sours, it’s no surprise. Aside from tasting fantastic brews, Captain Lawrence Brewing Company offers fun opportunities like trivia nights and live music.

People to Follow.

Want to know more about Sleepy Hollow and the neighboring areas and attractions? These are the places I turn to get excited about the upcoming season! Follow these accounts on social media:

Sleepy Hollow Spellbound 

Visit Sleepy Hollow 

Tarry In Town

TarryHollow Town