Travel Guide: Sleepy Hollow

This weekend marked my fifth fall adventure to Sleepy Hollow, aka North Tarrytown in the Hudson Valley of New York. When I lived in Ohio, I remember only dreaming of a trip to the village made famous by Washington Irving, so as soon as I moved to the city I made it my number one fall priority. It was better than I even expected, and I’ve gone every year that I’ve lived here—except 2016, but I went to Salem that year, so that’s a valid excuse.

There are plenty of non-Halloween related activities to do in and around Sleepy Hollow, but to get the full effect it’s best to visit in October (keep in mind that while it’s not as crowded as Salem, ticketed events sell out very quickly so get them as soon as they go on sale in early September from Historic Hudson Valley).

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GETTING THERE:

My favorite part about Sleepy Hollow is that you don’t need a car to get there. It’s under an hour by Metro North from Grand Central to the Tarrytown station, and trains run frequently. Once you’re in Tarrytown you can use a car service like Uber or Lyft to get you into town or to the sites nearby, but most things are within walking distance of the train station. We did have an issue once with spotty cell service when we were relying on Uber to get us back into town after visiting Union Church, but after renting a Zip Car one year (and dealing with the traffic on the one, two-lane road that runs through town), I’m solidly team public transit.

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WHAT TO DO:

Washington Irving’s Sunnyside

There is no doubt that Irving’s short story, The Legend of Sleepy Hollow is the reason why the area is a popular October destination. In fact, North Tarrytown officially changed their name in 1996 to Sleepy Hollow, the traditional name for the area. Purchased by Irving in 1835, Sunnyside is a National Historic Landmark and a museum containing a large collection of Irving's original furnishings and personal items.

Located in the nearby town of Irvington, the house is open May-November and tours are led by guides in period costume. In the fall you can also “create Halloween-themed art activities, explore the grounds on a literature-themed scavenger hunt, play historic games, pose for a spooky photo op, and take in a shadow puppet performance.”

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Kykuit

Kykuit was the 40-room home of four generations Rockefellers, beginning with John D. Rockefeller, founder of Standard Oil and noted philanthropist. The stone mansion is situated on the highest point in Pocantico Hills, overlooking the Hudson River and on a clear day you can see the New York City skyline. In addition to the house, the property includes beautiful gardens and an impressive art collection.

If you want to see something specific make sure you choose the right tour—I’ve been twice, and I would definitely recommend making time for the grand or classic tours. Although Kykuit is located outside of the village, tours originate from the visitor center at Philipsburg Manor (across from the cemetery) and a shuttle bus takes you to and from the estate.

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Lyndhurst

Lyndhurst, a Gothic Revival mansion, was designed in 1838 and had five different owners from three different prominent families before it became part of the National Historic Trust for Preservation in 1961. The mansion is furnished with original furniture/décor from all five owners so the inside is just as interesting and historic as the outside (and, if I’m picking favorites, it’s my favorite of the historic homes in the area). The 67-acre grounds include the bones of the nation's first steel-framed conservatory, a stand-alone bowling alley, a rose garden and a children's playhouse all with sweeping views of the Hudson River.

Open for tours March-December, the mansion and grounds were decked out for Halloween when we visited. Even without the extra help, Lyndhurst is spooky enough on its own and has appeared in numerous movies and TV shows including two star turns as the Collinwood Mansion in the 70’s films House of Dark Shadows and Night of Dark Shadows.

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Union Church of Pocantico Hills

The church itself, built in 1921 by John D. Rockefeller, Jr., is pretty standard but the church’s rose window was the last work completed by Henri Matisse before his death in 1954. Nine other stained glass windows were created by Marc Chagall, who didn’t start designing in glass until he was nearly 70 years old. Other Chagall windows can be found around the world and in the UN building in New York.

The church is open from April-December with varying hours depending on the worship schedule, there is a suggested donation if you visit just to see the windows, and photography is not allowed inside. The church isn’t really within walking distance from the village (and it’s up in the hills), but it’s just a short car ride away (again, beware the spotty cell service).

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Great Jack O’Lantern Blaze

The Great Jack O’Lantern Blaze is what put this area on my radar eight hours west in Ohio. Held every year at the historic Van Cortlandt Manor in Croton-on-Hudson (not exactly walkable from town, but just a short car ride north), the Blaze seemingly gets bigger and more popular every year. Tickets for weekends close to Halloween sell out very quickly, but it’s worth some advance planning to see more than 7,000 hand-carved and illuminated jack o’ lanterns (spoiler alert: they’re mostly fake, but there are some real pumpkins mixed in). I’ve been to the Blaze twice and can attest that, while there are some repeats from year to year, enough changes that you could go again every year and still be thrilled.

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Horseman’s Hollow

Billed as “Sleepy Hollow’s premiere haunted attraction,” Horseman’s Hollow is like corn maze and a haunted house combined. Set outside on the grounds of Philipsburg Manor, guests—if you dare!—walk along a haunted trail populated by all types of spooky scenes and creepy people. I’ve never been a huge fan of paying to be frightened, but I’ve gone through Horseman’s Hollow twice and I think I finally understand the appeal of these attractions. Skulls, spiderwebs and mannequin parts don’t actually scare me—have you seen my apartment?—but there is a strange sort of thrill in watching your friends get (harmlessly) startled and in surrendering to it all yourself.

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Irving’s Legend

Speaking of tickets selling quickly, this is the first year I was actually able to secure tickets to Irving’s Legend, a dramatic retelling of the famous Legend. Held at the Old Dutch Church (located within Sleepy Hollow Cemetery), the story is told by one man, accompanied by one musician. It’s low-tech, old-fashioned storytelling at its best and it’s the perfect way to get acquainted (or reacquainted) with Irving’s spooky tale.

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Unsilent Picture

This was a new event for the 2018 season, an original silent film starring Bill Irwin accompanied by live musicians and special effects provided by a Foley artist. Inspired by Washington Irving’s The Adventure of the Mysterious Picture, the film was shot on location at Van Cortlandt Manor. I’ve never seen a silent film before, but I was just as interested in watching the Foley artist produce sound effects for every character as I was in watching the actual movie.

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Haunted Hayride

Details on when to secure tickets to the Village of Sleepy Hollow’s Haunted Hayride are a little murky but this year I just kept checking the website and eventually was able to buy tickets. Tickets go on sale “sometime in September” only through the villages’s website, and the Hayride is for two nights only—the Friday and Saturday before Halloween. It started raining just as we were settling into the bed of hay (pulled by a pickup truck), and it wasn’t nearly as scary as walking through Horseman’s Hollow—but we felt about as far away from New York City as we could get, while still being a short train ride away.

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Sleepy Hollow Cemetery

One of my favorite cemeteries (and I’ve seen…a few), Sleepy Hollow Cemetery is home to a number of famous residents, including a Rockefeller, a Chrysler, the Helmsleys, Andrew Carnegie, Elizabeth Arden and, of course, Washington Irving himself. Formally opened in 1849, the cemetery is 85 acres and has over 40,000 in-ground interments. They offer day and night walking tours but keep in mind if you’d like to explore on your own that the grounds close promptly at 4:30 pm every day.

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WHERE TO EAT:

Muddy Water Coffee and Café

Located on Main Street, just up the hill from the Tarrytown train station, Muddy Water is a great place to stop and fuel up before beginning your fall adventure day. There is plenty of cozy seating, the coffee was good, the blueberry scone was delicious (have them heat it up) and my order came to a very festive total of $6.66.

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Horsefeathers

This section is short because I really only ever eat dinner or lunch at one place in Sleepy Hollow—Horesefeathers—and I love it so much that I can’t bring myself to try anywhere else. Ok, so we did make the mistake of eating at The Huddle once and it was terrible, so learn from us (here is the Yelp review by my friend Alisha, detailing our issues) and stick with Horsefeathers.

Family owned since 1981, Horsefeathers is exactly the kind of dark, wood-paneled bar that you’d expect to find in the area, and I dream about their Knickerbocker burger (paired with a seasonal cider) all year long. As if that wasn’t enough of an endorsement, they’re usually playing a Halloween movie at the bar (one year it was Casper) and they have ancient boxes of Trivial Pursuit cards on every table (Sample Q: Which country pulled out of NATO in 1967?), so at least stop in for a drink.

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Want more? See all of my Sleepy Hollow posts here.

Sleepy Hollow, 2017

Before I ever moved to New York, I knew I wanted to visit Sleepy Hollow during October. I even put it on my silly list of things to do before I turn 30, and I crushed that goal. I'm now 32 and Sunday was my fourth (mostly) annual trip upstate to the village formerly known as North Tarrytown. 

I'm embarrassed to say that it took me far too long to read The Legend of Sleepy Hollow short story by Washington Irving. I don't know why I waited so long to pick it up—and the story is less than a hundred pages, so it only took me a day to read—but it definitely added to my enjoyment and appreciation of the area.

It might seem silly or pointless to revisit the same tiny town year, after year, but I'm always seeing something new. There is also a comfort to holiday rituals, and as soon as the leaves start to turn and I feel a chill in the air (something woefully missing this year—it was nearly 80 degrees on Sunday), I start looking forward to the fall pilgrimage. This year's group of adventurers included some newcomers, and it's nice to be able to introduce people to Sleepy Hollow and share the places that I've come to love so much. 

This year we spent the bulk of our time visiting two historic houses in the area—Washington Irving's Sunnyside and the Rockefeller estate, Kykuit—so we didn't have a lot of time to wander. We briefly peeked into the cemetery but unfortunately it had already closed for the day, and we ended the night screaming (and laughing) our way through the outdoor haunted maze, Horseman's Hollow. 

I love that the village of Sleepy Hollow has come to embrace their famous legend—the headless horseman is everywhere, showing up on their street signs, police uniforms, fire trucks and school mascots—and I would imagine that locals either absolutely love Halloween, or grow to hate the influx of visitors. Every year I find myself discovering a lovely house with a mansard roof, cornstalks tied to columns or pumpkins on a porch and thinking that it must be the most wonderful place in the world to call home—but living just an hour train ride away isn't too bad either. 

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Places to see: Kykuit // Sunnyside  // Lyndhurst // Union Church // Sleepy Hollow Cemetery

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Thing to do: Horseman's Hollow // The Great Jack-o-Lantern Blaze

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Places to eat: Horsefeathers

Sleepy Hollow, 2015

We recently went on our third annual day trip to the village of Sleepy Hollow—formerly known as North Tarrytown—which is located about an hour north of the city in the Hudson River Valley. Although Washington Irving published his classic short story The Legend of Sleepy Hollow in 1820, North Tarrytown didn't officially adopt the name until 1996.

The village is very small, but they definitely embrace its association with Halloween, and have fully adopted the headless horseman as their village mascot. He appears on everything from the street signs to the fire trucks, sanitation vehicles and police badges—even the high school football team is called the Horsemen.

We started off the day by seeing the Chagall and Matisse windows at Union Church, which is located in the picturesque neighborhood of Pocantico Hills, northeast of Sleepy Hollow. Photos aren't allowed inside of the church, but it's definitely worth the trek (we took Uber) to see the incredible glasswork by two insanely-talented artists. The Matisse window is widely believed to be his last work and Union Church is one of only three places in the US to see Chagall glass.

We wandered around taking in—and taking photos with—the festive sights, drank pumpkin beers and hot cider, took a lantern tour of Sleepy Hollow Cemetery, were scared and impressed walking through the creepy Horseman's Hollow and I came away with a floaty pen featuring the headless horseman—this is Halloween.

More Sleepy Hollow: The Great Jack 'O Lantern Blaze | Lyndhurst | Sunnyside + Kykuit | Sleepy Hollow Cemetery

The Great Jack 'O Lantern Blaze

Last year was my first time going to the Great Jack O' Lantern Blaze at Van Cortlandt Manor near Tarrytown/Sleepy Hollow, NY. I loved it so much that a few months ago we bought tickets and planned a return trip. After touring Lyndhurst in the morning, we hung around Sleepy Hollow until it was time to go to the Blaze—tickets really do sell fast, and 9:30pm was the only time slot available even a few months in advance.

It turned out to be a great time to go—we had just enough time to see everything before it closed at 11pm and there were hardly any children (aka ruiners of all events). Since I knew what to expect this year it might have been slightly less impressive than my first time, but it was still totally worth the price of admission.

Although there were some repeats, there was still a lot of brand new things to see, including a few Washington Irving displays (the Headless Horseman throwing his pumpkin head was great) and a fun 10th birthday cake to celebrate the Blaze's tenth year.

I'm sad that October is coming to an end, but I can't say that I didn't pack a ton of fall delights into the past 31 days. It's definitely my favorite month, and now that it's over I'll just go back to being that creepy coworker who wears skull socks and talks about cemeteries all year long.

Lyndhurst

On Saturday three of my friends and I went to Sleepy Hollow/Tarrytown for a day filled with fall delights. We had gone last year for the first time, and loved it so we knew we'd be back. One thing we didn't do last year was tour Lyndhurst, "one of America’s finest Gothic Revival mansions," so it was our first stop this year.

Lyndhurst was designed in 1838 by Alexander Jackson Davis and had five different owners from three different prominent families before it became part of the National Historic Trust for Preservation in 1961. The mansion is furnished with original furniture/décor from all five owners so the inside is just as interesting and historic as the outside.

Of course since it's October, the mansion was also decorated for Halloween, which I would usually be annoyed about if it didn't naturally fit so well with the gothic architecture and if I didn't love Halloween as much as I do.

There were tombstones out front, ghouls in the trees and spiderwebs on everything. They even had a few pieces of mourning wear on display, and one very awesome example of Victorian memorial hair art (when asked if anyone knew what it was made from, I was the only one to very enthusiastically—and totally embarrassingly—yell out, "HAIR!"). 

The grounds of the estate are worth a visit alone. Before we even took the house tour we saw the bones of the nation's first steel-framed conservatory, a shingle-style, stand-alone bowling alley, Jay Gould's footbridge—over the railroad tracks and down to the river—that he used to board his boat, a rose garden, a children's playhouse bigger than most New York studio apartments and sweeping views of the Hudson river.

Lyndhurst was also used for the filming of two Dark Shadows movies in the '70s, which I have never seen but I will definitely be tracking down soon. I dream of one day owning a real-life haunted mansion that I can fill with taxidermy and curiosities and clones of Mozart (my cat)—I wouldn't mind having my own bowling alley either.

Sunnyside and Kykuit

Before we visited the final resting places of both Washington Irving and William Rockefeller on our recent trip to Sleepy Hollow, we toured their respective estates, Sunnyside and Kykuit. They are geographically almost neighbors, but the properties are very different.

Sunnyside is more of a cottage, although Irving (who never married) shared the relatively small space with his brother and his five daughters. The house sits on beautiful former farmland, separated from the Hudson River by train tracks, an addition that was made back in Irving's time. Four of us actually got into Sunnyside for free because the fifth person in our group became a member of the Historic Hudson Valley. I think I may have been disappointed if I had paid the $12 admission price, but as I've said before I have a hard time complaining about something I got for free.

The tour encompasses only a few of the ground floor rooms, and we were free to explore the grounds (including the outhouses and icehouse) on our own. I wish we had been able to see more of the house and I felt as if the guides stationed in each room were a bit less enthusiastic with their stories than I expected.

Later in the day, as we were standing in front of Irving's grave in Sleepy Hollow Cemetery, we overheard the following conversation between a husband and his wife: "Who was Washington Iriving again?" "He's the one who wrote the Headless Horseman."

They definitely could have benefited from the tour at Sunnyside, but since we already had a cursory knowledge of the man who wrote the inspiration for our entire trip (which is The Legend of Sleepy Hollow, by the way, not the Headless Horseman) it was interesting but not terribly enlightening.

Down the road a bit is the Rockefeller estate, Kykuit (pronounced Kye-cut), which is much larger and more grandiose than Sunnyside. We were wary of our tour guide at first, but aside from her creepy obsession with Nelson Rockefeller, she ended up being pretty great.

The house is beautiful, but it's the location and the grounds that really make it a spectacular place. The sloping lawns overlook the Hudson River Valley and I can't imagine a more beautiful time than fall to take the tour. Again, we didn't see as much of the house as I would have liked (why are the top floors always off-limits?) but it was still pretty long and informative.

Apparently the Rockefeller's tried not to be too showy with their wealth in keeping with their Baptist beliefs, but I'm not sure how much they succeeded in that regard. If Kykuit is their idea of what restraint looks like, I'd love to see what it would have looked like had they really tried to show off.

The Great Jack O'Lantern Blaze

One of the very first things we did when we were planning our trip to Tarrytown/Sleepy Hollow, was book our tickets for the Great Jack O'Lantern Blaze. The hugely popular event sells out quickly, with some of the more in-demand dates (weekends close to Halloween) and times snatched up before fall even begins. When we went to book our tickets (in September) the only weekend time available before Halloween was Sunday, October 27th at 9pm. We grabbed them, and planned our day around the Blaze. I'm so, SO glad we did because it was definitely the highlight of the trip, and a great way to end the night.

I actually discovered the Blaze a few years ago when I was still living in Ohio. I obsessively read all about it (including their hilarious faq page) and tried desperately to figure out a way to make an October trip to the Hudson Valley happen. Fast forward a few years, I'm living much closer to the action and one of my friends mentions that he'd like to take a trip to Sleepy Hollow in the fall. He had never heard of the Blaze before, but it didn't take much convincing to get him (and then the rest of our group) to trust my enthusiasm enough to book our tickets more than a month in advance.

In all of my planning and research I had somehow misread the descriptions, and initially thought that there were 500 pumpkins, which seemed like a lot to me. That is, until I read it correctly and realized the Blaze featured more than five THOUSAND hand carved and lighted pumpkins. Turns out that only about 1,000 of those are real — the rest are plastic, carveable "funkins" and reused year after year. This really doesn't affect the integrity of the event, however, and it's nearly impossible to even tell which ones are real and which are fake. As far as I could tell all of the ones closest to the path were definitely real and it's so dark and they're SO BRIGHT AND SHINY, so who cares in the end. Seriously, the entire thing was dazzling and even though I was there I still can't really fathom that I saw more than 5,000 pumpkins.

There were your standard, "face" carvings (in every variety you can think of, and then some), but the more elaborate displays really stole the show. It's impossible to pick favorites — from dinosaurs and zoo animals, to witches, mummies, skeletons, spiders, bees, bats and an entire yard of cat pumpkins (ok, I might have actually squealed with delight upon seeing so many cat pumpkins) — there was definitely something for everyone.

There was a grandfather clock with a swinging pendulum, jack-in-the-boxes with pop-up pumpkin heads and a new-this-year, walk-through tunnel lined with hundreds of carved pumpkins.

The event was very nicely controlled, with a winding, roped off path that you followed through the entire grounds. This made sense to protect the pumpkins, but also gave you unobstructed views of every single carving. The low-light does make it difficult to get great photos (with an iPhone at least), but please don't be one of those people that thinks turning the flash on will give you a Pulitzer-prize winning shot. All it actually does is give you a crappy, washed out photo of pumpkins, where you can't even see the carvings and the person next to you can't see anything at all for a few minutes.

There was a bottle-neck at one point in the pathway, where we had to wait about fifteen minutes to keep moving, but otherwise the night was as smooth as can be, especially considering the crowd. Parking was free (always a plus), and there's a tent to wait in until your admission time, although we were allowed in a few minutes before nine.

We had just eaten dinner so we didn't partake in any of the food, although had I known that they had apple cider donuts I definitely would have come home with some. They even sell a soundtrack made up of original music composed specifically for the Blaze (they're on volume IIalready). The displays change a bit every year, so I definitely want to make the Blaze an annual tradition — especially now that I'm only a short Metro-North train ride away.

Happy Halloween!

Sleepy Hollow Cemetery

On Sunday a group of friends and I spent the whole day exploring Tarrytown and Sleepy Hollow in the Hudson River Valley. We'd been planning the trip for a while, and I can't remember being as excited for anything in quite a while. I'd never been to upstate New York before, and Sleepy Hollow seemed as if it would be the epitome of all fall and Halloween delights. The area definitely did not disappoint, and we crammed a ton of adventures into the more than 12-hour trip.

A definite highlight was the Sleepy Hollow Cemetery and Old Dutch Church Burying Ground. There are a lot of famous New York names buried in the cemetery, including a Rockefeller, a Chrysler, the Helmsleys, Elizabeth Arden and, of course, the area's most famous resident, Washington Irving.

The grounds are incredibly beautiful, especially this time of year. The entire area was exploding with fall colors, and the higher ground overlooks the Hudson River Valley, which is one of the most spectacular sights I've seen. Every corner I turned there were more and more beautiful trees and the weather was perfect.

The cemetery is a mix of old and new tombstones, fancy mausoleums and gorgeous statues — they apparently still have plots available if you're in the market for one. I can't think of many better places to spend all of eternity, but it was also a great place for a leisurely Sunday stroll.

The Pocantico river runs alongside the cemetery, and although the original "headless horseman" bridge is no longer standing, there is a rustic bridge that, according to the maps, "makes a nice souvenir photograph."

The Old Dutch Church is small and plain, but the churchyard has some of the oldest graves in the cemetery. I'll never get tired of exploring historic cemeteries, and there is always something new and interesting to discover. A lot of graves were even decorated for Halloween with pumpkins and flowers, which was appropriately festive. They offer tours during the day, but also after dark which might be neat to check out if I go back next year. I can easily see an October trip to Sleepy Hollow becoming a tradition, and there is plenty that I didn't see the first time around.