Visit Legendary Sleepy Hollow Country | Halloween Happenings NY Travel Guide

Sleepy Hollow, NY is a well-known little village from Washington Irving’s famous short story “The Legend of Sleepy Hollow”. But, did you know it is also a real town that you can visit?

We want to show you our favorite spots in this town of legends and lore. A town where the line between fiction and reality is as blurry as the morning mist rising from the Hudson River. In fact, it takes both the villages of Sleepy Hollow and Tarrytown to uphold the spirit of Halloween all year round.

LEGENDARY LOCATIONS (From North to South)

– Sleepy Hollow Cemetery

– Washington Irving’s Grave

– Old Dutch Burying Ground

– Headless Horseman Statue

– Philipsburg Manor

– Sleepy Hollow Main Street

– Patriot’s Park

– Tarrytown

– Lyndhurst Manor

– Washington Irving’s Sunnyside

– Armour-Stiner Octagon House

– The Great Jack o’ Lantern Blaze

– FAQ | Tips for your Sleepy Hollow Visit

First, A Little Legendary History

It all started in the mid-1600s, when Dutch settlers colonized the area of New York. Some of them found their way to a dreamy area near the river, that in 1996 would be renamed from “North Tarrytown”, to “Sleepy Hollow”. Although, before new street signs were re-painted, and old maps re-printed, its name first appeared in a much-beloved short-story, published for the first time in “The Sketch Book” 1820, written by Washington Irving.

“The Legend of Sleepy Hollow” has since then become a literary classic, known, beloved, and appreciated by almost everyone. It is such a pleasure to be able to visit this old and historic Dutch village upon the historic Hudson River and perhaps also spot “the Headless Horseman” while retracing the steps of a certain schoolmaster, Ichabod Crane.

PLEASE NOTE

This post features our personal favorite Local Haunts & Happenings in Sleepy Hollow & Tarrytown. Even as locals, we haven’t experienced everything that the area has to offer and each year events come and go. Please take a look at VisitSleepyHollow.com for a comprehensive guide of what to see, do, and stay, plus a calendar of events to help plan your trip! Please also consult the Halloween in Sleepy Hollow Guide to plan your October visit. Don’t lose your head, let’s begin the Halloween Town Tour. *PLEASE* Adhere to the code of conduct for each location as some allow photography and some don’t (and some gave us special permission to share)

Sleepy Hollow Cemetery

When you visit Sleepy Hollow, let’s begin by visiting those who once wrote its rich history. In Sleepy Hollow Cemetery you can wander for hours and dream up all kinds of stories. It is a beautiful and still active cemetery worth a lot of time and respect. We recommend beginning your day at the Sleepy Hollow Cemetery since the gates close at 4:30PM. Book a Cemetery Tour by day or night and even by lantern light in the fall.

There you can find your way down to the Pocantico River to see the Headless Horseman Bridge where you can sit down for a moment while listening to the water that some days might whisper “Ichabod, Ichabod, Ichabod”. Many expect to find a covered bridge but there is no evidence that would have been the case here. Although, the original bridge would have been located a little farther up the stream, this Tim Burton-esque representation has such a whimsical touch.

Washington Irving’s Grave

On this hillside of the cemetery overlooking the Old Dutch Church, you can visit the legend himself, Washington Irving, where every October a pumpkin ordains his resting place.

Old Dutch Church and Burying Ground

You might not know when you enter the border of these two cemeteries, but the Old Dutch Burying Ground is a separate resting place. It is much older and here stands the oldest church in New York state, the “Old Dutch Church” built 1685. Pick up a map there or stumble upon some other familiar names such as Van Tassels. Take a walking tour led by the Sleepy Hollow Historical Society for history to really came to life as you wander the gravestones learning some of their stories (and of course some legends too).

You might start to hear the hoof beats in the distance, and imagine that you see a headless horseman in the corner of your eyes. If you do it is no imagination since you can actually meet him there once in a while, especially during the Old Dutch Church festival which used to be held on weekends in October!

Please remember to respect this sacred grounds since it is a resting place and not a park. You never know when you might be walking on the unmarked grave of the Headless Hessian soldier.

Weekends in October, you can attend a spellbinding storytelling about Hulda of Bohemia the “Witch of Sleepy Hollow” performed by Carla & Keyes inside the Old Dutch Church.

Headless Horseman Statue

Unveiled in 2006, this18-ft tall steel sculpture of The Headless Horseman chasing Ichabod Crane is popular spot for photos, especially in October. It’s on Route 9 just a few feet away from the original bridge outside the Old Dutch Church following the river to Philipsburg Manor (watch out for the traffic as you cross).

Philipsburg Manor

If you’d like to experience what the village life of c. 1700s would have felt like in Sleepy Hollow then step back in time to Philipsburg Manor. Cross the old millpond bridge to learn how Dutch, African, and Native American cultures became entwined at this colonial outpost. During October you can also experience their popular haunting Halloween event, called Horseman’s Hollow (although it has not been happening since 2020)!

Village of Sleepy Hollow

Sleepy Hollow’s main street “Beekman Ave” is worth a stroll especially in October when the town clock is decorated with “Jack” the scarecrow. It is an experience to see their orange street signs and notice the many hints towards the old legend with the horseman here and there. The fire station has a stained glass window of the Horseman as well as on their firetrucks. In mid-October the Sleepy Hollow Street Fair lines the street with vendors of arts, crafts, and entertainment!

Down by the Hudson River banks is the Sleepy Hollow Lighthouse (also known as the Tarrytown Light). You can reach it via the Scenic Hudson RiverWalk trail.

Patriot’s Park

Along Route 9 you’ll find Patriot’s Park, so named for it’s historical significance. The Andre Monument marks the year 1780 where three local militiamen captured British spy John André, which exposed American general Benedict Arnold’s treasonous plan to turn over the fortifications at West Point to the British. This is also where Ichabod Crane is said to have first encountered the Headless Horseman.
Half the park rests in the Village of Sleepy Hollow and the other in Tarrytown.

The “TASH” Farmer’s Market takes place at Patriot’s Park on Saturdays May-Nov where local vendors from across the Hudson Valley gather to sell their fresh produce, baked goods, and our favorite apple cider donuts.

Village of Tarrytown

In the neighboring village lies Tarrytown. It’s our favorite place to go for shopping and refreshments. ON Broadway street you will find our favorite souvenir shop Bella’s Boutique which has a lot of nice Sleepy Hollow prints, postcards, gifts, and jewelry. If you enjoy the vintage style, “Pretty Funny Vintage” might be an interesting shop to visit as well.

On Main street, there are many shops, restaurants, and cafes. In the summer you can experience the Tarrytown Street Fair and in December there is the Winter Stroll for your holiday shopping.

In the autumn the historic Tarrytown Music Hall hosts Ghost Tours. At the end of October you can experience the Halloween Parade and Block party which feels like a real life Halloweentown where all the ghouls and goblins of the villages of Sleepy Hollow & Tarrytown come together to celebrate.

The Historical Society, Inc. of Sleepy Hollow & Tarrytown has been the keeper of the collective memories of the villages since 1889. Since 1952 the Jacob Odell House has been the headquarters for The Historical Society, within its walls are museum exhibit rooms, a library, and storage rooms dedicated to preserving local history. Visit and see what historical exhibit is currently on display, you can usually see many Irving artifacts!

We always end our Sleepy Hollow days by eating at our favorite restaurant that is called Horsefeathers. They are serving a nice variety of meals and drinks, but are most famous for their delicious burgers. All are served in a cozy atmosphere that reminds us of an old writer’s study room. You almost expect Washington Irving to walk in through the door any minute, followed by his many old author friends that grace the walls in a charming mural.

We think every visit to the Hollow should include a harvest feast befitting Ichabod Crane! Our personal favorites are the butternut squash soup, Thanksgiving “gobbler” sandwich, hot apple cider, and warm apple pie! Tip: The portions are very generous to it’s easy to share and make sure you save room for dessert!🥧

LYNDHURST MANSION

Further down the Hudson River you’ll find Lyndhurst Manor, a gothic revival estate of mystery and glamour. Surrounded by a 67-acre park it makes a wonderful place to stroll and especially to see the Rose Garden blooming in June. Indoor tours give a glimpse of three influential families that lived here and added their history.

Did you know that Lyndhurst Manor has served as a filming location for some well-known movies? Most notably the vampire TV series “Dark Shadows in the 1970s. For a ghouls night out, you can experience the mansion draped in candelight at a Lyndhurst After Dark tour and learn Victorian Halloween traditions and afterlife superstitions.

SUNNYSIDE | Washington Irving’s Home on the Hudson

Along the banks of the Hudson river lies the home of the legend, Sunnyside, once the home of the beloved author Washington Irving. After becoming one of America’s first success authors and spending 17 years abroad; Irving returned to Sleepy Hollow for which he had by then immortalized in his ghost story of the Headless Horseman. You can tour his romantic and whimsical “cottage” or just visit for a peaceful walk around his garden. Whatever you do, we are sure you’ll learn something new about the “founding father of American literature.” You might understand how he got such inspiration from the Hudson Valley to write the classics, like “Rip Van Winkle” and “The Legend of Sleepy Hollow”.

This place has the perfect atmosphere for any cozy spooky tale, especially by renowned Hudson Valley storyteller, master Jonathan Kruk who spins the story of Irving’s Legend. Mind your head, the Headless Horseman is known to make an appearance!

Armour-Stiner Octagon House

Irvington, New York’s most iconic house is an 8 sided wonder of architecture built in the 1860s! There are several themed tours throughout the year where you can learn about the fascinating creation and family stories.

We enjoyed the Myths & Mysteries tour where you can learn about the house’s ghostly residents. “Cabinet of Curiosities” By Ryan Matthew Cohn can be seen on display during spooky season.

Please Note: The Octagon House is a private residence so you must book a scheduled tour to be on the premises.

The Great Jack o’ Lantern Blaze

The Blaze is New York’s original spooktacular Halloween event located at historic Briarcliff Manor in Croton-on-Hudson (about 20 mins by car North from Sleepy Hollow). Witness the night sky lit up by thousands of hand-crafted pumpkins as you walk along a winding trail to different themed areas all to a spooky score of music.

FAQ | Tips for your Sleepy Hollow Visit

Thank you for letting us guide you through our favorite parts of Sleepy Hollow and Tarrytown, we hope you feel inspired to visit Sleepy Hollow yourself! We often get asked for our travel tips and recommendations. PLEASE NOTE: Sleepy Hollow & Tarrytown are villages where people live and work, thousands of people come to visit in October so please be kind, respectful, and patient as the villagers do their best to cater to the tourists. Here are our most asked questions:

When is the best time to go? The best time to visit depends on if you want to experience Sleepy Hollow during the hustle & bustle of Halloween season or not. Early-mid September is a nice to experience some early events and perhaps get a little bit of fall foliage. Halloween decorations don’t usually go fully up until October but that is also the height of tourism season. We like to suggest early November, since there the decorations and leaves usually still linger plus certain events like The Blaze are still running. The holidays in Sleepy Hollow are also a nice time to visit and see Irving’s Old Christmas.

How many days do you need to experience Halloween in the Hollow? A few days or a long weekend will give you plenty of time to see the villages and attend a few events. The key is to find which events you are most excited for since there are so many things running during the month of October.

What are the must see Halloween events? Please note, most tickets go on sale as early as August and once they are sold out they don’t often add more. It’s a good idea to sign up for the Historic Hudson Valley’s event email list to get announcements of popular and new events. A storytelling performance of The Legend by Jonathan Kruk is not to be missed and The Blaze is a fan favorite. A newer shows we recommend is Hulda the Other Legend.

Where can you see the Headless Horseman? The appearance of the Hessian soldier is often a mystery but he has been seen at The Old Dutch Church Burial Grounds, Washington Irving’s Sunnyside, and leading the Halloween Parade. Of course, the real spirit that haunts the Hollow is perhaps looking over your shoulder.

Where are the best places to stay? There are several places to stay in Sleepy Hollow Country but we have never personally been to any of them since we are locals. At this time, there are no lodgings in the village of Sleepy Hollow or any inns/bed & breakfasts, hopefully some day!

Where is the best places to eat? Both the villages of Tarrytown & Sleepy Hollow have wonderful dining options. We haven’t tried them all but Horsefeathers Restaurant will always be our top recommendation (and our favorite booth is where you find the “Haunted Cat Portrait”)

Where are the best photo spots? We’ve already shown several of our favorite photo locations throughout this post but we can suggest a few more (coming soon)

Are there any “secret spots” or hidden gems? There are many hidden gems of lore & legends throughout Westchester County. We suggest following our Instagram friends at @SleepyHollowCountry and @SleepyHollowSpellbound for lots of great photos and videos. The Witch Mural by @martinmunroe can be found in the Rockerfellar State Park but you must take a journey to find it.

Where can I buy souvenirs and see Jonas’ pumpkins and art? There are a handful of gift shops across both villages, some are seasonal and some are open year round. You can purchase Jonas’ spooky art prints, postcards, bookmarks, and more at Bella’s Boutique. We occasionally host a pop-up shop outside the shop on a TBA weekend in October. Jonas art pumpkins can be seen at different locations depending on the year; Horsefeathers has a growing collection in the restaurant and The Octagon House has one on display in October.

What’s the best way to get around the villages? The best resource about transportation and directions is from VisitSleepyHollow.com. Keep in mind that in October, traffic increases and parking is more scarce.

Any tips for a legendary experience in Sleepy Hollow Country? YES! We always recommend to read Irving’s short story “The Legend of Sleepy Hollow” before (or during) your visit for the best experience of feeling like you’re walking in the path of Ichabod Crane! Go into your visit with an open mind, the villages may not look like a Tim Burton movie set everywhere you go but the history is entwined with the very nature of this Halloween town we call home.

– Lindsay Dianne & Jonas

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