One of the most splendid travel destinations in the world is only fifty minutes north of New York City. Also, as an avid fan of Halloween, I wished for most of my life that a town devoted entirely to the holiday existed. As an adult, I finally found my macabre utopia. Sleepy Hollow, New York, complete with its lore and cemetery, is a fantastic spot to visit in the fall, and it’s a remarkable destination for children. It was incredibly easy to visit with a five month old, and grandparents in tow.

Meeting the Headless Horseman in the Old Dutch Church’s Graveyard.

The “founding father” of American literature so to speak has strong roots in Sleepy Hollow, New York. Sleepy Hollow is actually formally called Tarry Town. Washington Irving, one of America’s first famous writers spent a lot of time in the resplendent wilderness of the village as a child. He became so enamored with the area that Tarry Town became the inspiration for his setting in what would become one of his most famous pieces “The Legend of Sleepy Hollow.” This story would go on to bring him international fame and win him influential friends such as Charles Dickens and Mary Shelley. One of the most infamous characters in his ghoulish work is the terrifying “Headless Horseman” who has a pumpkin for a cranium. The legend states that he roams around on horseback at night looking for heads to steal!

On some October days, you can hang out at the Old Dutch Church graveyard and wait for him to make an appearance. The Old Dutch church dates back all the way to the 1600s. You can listen in on a lecture of its history as we did. Or, if you have children who are older – catch a performance of The Legend of Sleepy Hollow inside of the church. There’s nothing cooler than hearing a famed storyteller and musician take you through the frightening legend as the wind rattles the windows of the old church! Click here to find out more about that.

The Great Jack O’ Lantern Blaze.

This is one of the activities that make a visit to Sleepy Hollow so memorable. The Great Jack O’Lantern Blaze is an exhibit of hundreds of pumpkins carved, lit, and arranged into unbelievable works of art. It can be extremely difficult to find an activity that everyone in the family enjoys, but from the oldest to the youngest, everyone was impressed and blown away by the creativity and ingenuity of the blaze. This is Halloween in its best form. The opportunity to see these Jack O’Lanterns in person quite literally takes your breath away.

You MUST purchase your tickets in advance, especially if you are traveling during COVID. This is one of the few activities open, and it operates at a reduced capacity, so tickets will disappear soon.

It will get very chilly at night, so layer up! We were nervous that our five month old would be too cold. I was thankful that we found just the remedy. I cannot recommend this item enough if you share the same concern regarding your little one freezing. It was a lifesaver.

Meandering Sleepy Hollow’s Cemetery.

The Old Dutch Church dates all the way back to 1685! Naturally, the attached graveyard has a ton of history. When walking through the graveyard, you’ll notice that quite a few gravestones have an American flag and placard in front of them. This is an indication that these deceased individuals have served in the American Revolutionary war. It’s remarkable to read the inscriptions on the tombs and imagine why each person beneath them felt compelled to aid in the events that would eventually create the United States. Typically, you might feel that walking around a cemetery is a solemn activity, but the Sleepy Hollow cemetery is actually quite jovial. In October, beer, crafts, and food are usually served in the graveyard.

Directly beyond the graveyard, if you keep walking, is the Sleepy Hollow cemetery. Washington Irving, the author mentioned above, is buried here. The cemetery is an outdoor museum of sorts—meant to be beautiful and enjoyable enough for families to picnic and spend plenty of time while visiting their deceased loved ones. To find out who is buried here, and why, consider taking a cemetery tour. During our first visit, we did an evening tour. You get to carry lanterns around and listen to the terrifying tales! With the chill in the air and the pitch black sky, this probably won’t be suitable for babies, so consider doing a daytime tour instead!

The Legend of Sleepy Hollow Commemorations.

There are some free and easy things to do with your baby that make for a great photo op. Visit the Headless Horseman statue right outside of the cemetery. Marvel at the unique artistic display and consider how Ichabod Crane felt with the Horseman breathing down his neck and ready to decapitate him.

As the legend goes, when Ichabod Crane tried to outrun the Headless Horseman, he knew he could be safe on one condition. If he could manage to get across the Sleepy Hollow Bridge and into the sanctity of the Old Dutch Church area, the Horseman would not be able to touch him. Walk across the bridge and imagine Ichabod going as fast as he can to try and get to safety. If you’re one of those annoying athletic types, see how fast you can run across the small bridge!

Farmer’s Markets.

Not everything in October needs to be Sixty Shades of Spooky. One of the greatest parts of autumn is that it’s harvest season. Visit the two farmer’s markets in town for your opportunity to meet locals and browse heaps of quality produce, creamy cheeses, fresh cut flowers, and souvenirs. There’s the TASH(Tarrytown and Sleepy Hollow Farmer’s Market) as well as the Irvington Farmer’s Market.

If you’re into bargains, often times the Union Church of Pocantico Hills in town has great deals on thrift items. I’ll never forget when came across thousands of barely used books for a dollar a piece. Sometimes you can find toys for your little one too in need of a new loving home.

Mansion Tours.

There are two major mansions in the area and both have very storied histories. The Lyndhurst Mansion often decorates really well for Halloween. Even if you don’t do the tour, you can admire the awesome decorations and take lots of photographs. The home looks more like a castle out of the medieval days than a dwelling and can only be explored by guided tour.

The more familiar mansion is Kykuit, which was home to four generations of Rockefeller family members. Their level of wealth is something that really needs to be seen to believed. If you’re anything like me, you won’t be able to stop thinking about their lavish home for weeks! Guided tours are required for exploring the mega mansion.

Sunnyside Estate.

There’s something especially soothing about visiting Sunnyside, it’s almost as if it were plucked straight from the pages of a children’s fairy tale book. With its rolling green hill, scavenger hunt designed for kids, and offerings of fall snacks and warm cider, it’s really fun.

The home belonged to Washington Irving who was the creator of the Legend of Sleepy Hollow which has international acclaim and is the basis for the Sleepy Hollow town. You can take a guided tour led by a costumed docent. They’ve kept the home very much the same as it would have been when he lived there.

You’ll see some spooky sites like a magic crystal ball sitting on a table, and a strand of garlic meant to keep vampires away. The guides do a great job of explaining the connection to history of the time.

With its narrow hallways and small rooms overlooking the Hudson River, it’s easy to fall in love with this charming estate. In fact, many people in the olden days DID have a souvenir photo of this estate in their homes on display, Washington Irving was a popular guy!

The Halloween Parade.

Even if you’re not a local of Sleepy Hollow, you can join in the fun of its Halloween celebration! The parade falls on only one day each year, and everyone from participants to spectators wears their costume in celebration. The parade marches down Main Street and ends with a DJ, performances, snacks, outdoor dining and more.

NOTE:

Things change every year in Sleepy Hollow. Note that with the COVID19 pandemic still raging on, some activities which used to be indoors are now outdoors. This is great for families with babies as it allows for an easy escape if your child starts to get fussy. You can always walk away to a far off spot until your baby calms down, and then go right back to your seat when they do!

Check this website for the most up to date information

Dining Out with Baby in Sleepy Hollow.

I’ve found restaurants everywhere in and around Sleepy Hollow to be fairly accommodating towards children. This is especially the case during breakfast and lunch. Don’t forget that many restaurants will allow carry out and you can eat in your hotel room or house rental. There is one restaurant that I really love which made dining with our baby a breeze!

Guadalajara

This is my favorite restaurant in Tarry Town/Sleepy Hollow. If you’re interested in having some of the best Mexican food of your life, be sure to make a reservation, especially during busy season! A number of celebrities have eaten here, and there is a wall filled with photos of the famous at the entrance of the restaurant for proof.

I consistently leave here feeling as though I’ve gained 20 pounds at least. I highly recommend the queso fundido (if you’re a cheese fanatic) and the chorizo espanoles as appetizers. You’ll for sure want to get a margarita as a pat on the back for making it through the day with your beloved children. But, why go with the original flavor when you can choose wild-berry, mango, or coconut? If you’re not a tequila fan, or rather, tequila isn’t a fan of you – spring for the sangria!

Guadalajara is especially amazing around Halloween time because all of the staff dresses up in a MAJOR way, costumes, face paint, the whole ordeal! The staff is also really great with children. They took and stored our stroller right away and helped us navigate how to seat our child in his car seat at the table. The restaurant is loud, so if your baby stirs or whines, he or she won’t bring too much attention. My rule of thumb is always spring for noisier places when dining out with little ones.

nervous to bring your kids to a restaurant? Check out my guide on dining out with baby

There are a plethora of places to eat in Sleepy Hollow/Tarry Town, and I wrote about some here. 

Just know that you have plenty of options! From Korean to Greek to Barbecue…you’ll always find something that you like!

Fun for the Whole Family. 

So, yes, Sleepy Hollow New York is absolutely baby friendly. I would have no hesitations about bringing your family here as it’s typically filled with children, grandparents, and caregivers. It’s an easy trip especially from New York City, and yet it feels world’s away. The town oozes with Halloween spirit and is set against some really splendid nature, you might feel as though you’ve tumbled back a few centuries. In today’s constantly connected, technological world it’s nice to give your children a glimpse of the simpler Halloween that we enjoyed as kids!

Happy Halloween!