Welcome to the Neighborhood: Sleepy Hollow & Tarrytown

In the name of small scale adventure, I’m spending one day each month exploring an area in or around New York City that I’ve never been to before. Welcome to the neighborhood.

This month’s neighborhood was decided in January. October is the perfect season for an “upstate” adventure and no town has a stronger hold on the month than Sleepy Hollow. At the suggestion of a friend, we covered two neighborhoods—Sleepy Hollow (Philipse Manor) and Tarrytown. It was a charming day that I would run back a million Octobers over. Let’s dive in.

My friend and I met at Grand Central and took the 10:25 train to Philipse Manor. That got us in at 11:21. I will never get over the charm of getting on a train, chatting for an hour, and stepping out in an entirely different world. It happened that we went on just about the perfect fall day and the moment we left the station felt like walking onto the set of your favorite fall film.

The distance to downtown Sleepy Hollow is about a mile, but we reveled in the houses and the Halloween decorations, discussing whether our city selves would ever leave the 5 boroughs. Located 28 miles north of Manhattan on the east bank of the Hudson River, Sleepy Hollow is most known for the Washington Irving short story, “The Legend of Sleepy Hollow.” I’m embarrassed to say that I have yet to read it or to see the 1999 Tim Burton film. But in Sleepy Hollow, the legend is unavoidable. It’s a town that really leans into its season.

We first came to the Old Dutch Church and the Old Dutch Burying Ground. In town, there’s the famous clock and jack-o-lantern, a mural, and a headless horseman statute. And everywhere you turn, you see skeletons and pumpkins, ghost and goblins. Halloween is my second favorite holiday (New Year’s Eve heads unite!) and I think this was the perfect way to kick off the season.

The first place we really stopped was the Sleepy Hollow Bookshop. I got The Origin of Sleepy Hollow: The Name and the Village by Christopher Skelly and I can’t wait to dive into authentic local history. In addition to being a very cute bookshop (mostly focused on children’s books), they also have a small cafe.

From there, we went to the Village Confectionery, a whimsical, old school candy shop. Candy corn, chocolate pumpkins, and gummy body parts abound (in addition to the year-round classics). The place was filled with residents and tourists young and old, eyes gleaming at the sweet treats and nostalgia bubbling over like a witch’s cauldron.

Our final stop in downtown Sleepy Hollow was Sleepy Coffee, Too. Sleepy Coffee, Too, is a nonprofit cafe that “provides on the job industry level training and employment for people with disabilities in an inclusive, self-sustaining cafe workplace.”

It was immediately apparent that this was the place to be; the line was nearly out the door! From their website, I learned that high school graduates from special education programs have limited meaningful work opportunities and that unemployment sits at around 80%. Their solution was an inclusive workspace through the means of a coffee shop and bakery to not just provide employment but to combat depression, isolation, and dependency on others. They have all your coffee shop classics, homemade treats made fresh daily, and even biscuits for our dog friends.

While there is so much more to see in Sleepy Hollow, we headed down to the water to do a 45-minute guided tour at the Tarrytown Lighthouse in Sleepy Hollow. You do need to make a reservation for this tour but it is otherwise free and I think the highlight of my day. I’m writing this 3 weeks after my day in Sleepy Hollow and regretting deeply that I cannot recall the name of our tour guide who was really informative about the lighthouse but more importantly, sincerely passionate about conservation and the park system.

At the tour, we learned that this lighthouse is short and stout and that it is referred to as a “sparkplug” lighthouse. The most fascinating thing I learned was that the lighthouse (that is only presently a couple dozen steps from land) used to be a half mile from shore. The riverwalk, the Metro North line, all of that used to be the Hudson River but in the mid 1800s and early to mid 1900s, a massive industrial push changed the shoreline forever.

In 1915, General Motors began production at an assembly plant in what was then North Tarrytown (now Sleepy Hollow). According to our tour guide, townspeople used to know what color the cars were being painted that day based on what color the river turned. In 1996, the GM plant closed. I had no idea the shoreline—that much of the shoreline up there—is entirely artificial. I’ve bookmarked this as a deep dive topic for another time.

We also learned about the lighthouse keepers. At every moment, two adults needed to be in the lighthouse. Often, the second was the lighthouse keeper’s spouse or, if they were unmarried, an apprentice. The whole family lived in the lighthouse and that sometimes included pets (chickens, rabbits, dogs). We learned about “Lighthouse Larry,” the only “seabound student” at the local high school who would paddle the half mile back and forth from school. If the weather wasn’t conducive to returning home, his father would show a specific light at the lighthouse to let him know to stay with a friend in town that night as opposed to paddling back to the lighthouse.

At one point, the tour guide asked why we thought there was a collection of rocks making a sort of loose perimeter around the lighthouse. I wanted to raise my hand and say something about big boats crashing into the lighthouse, but if you were to crash into the only light on the river, perhaps there are bigger problems. Turns out, that is not the answer. The stones are called riprap and the purpose is to break up ice so it cannot impact the lighthouse foundation.

It was such a fun treat to be able to tour a lighthouse (and, from the top, to see incredible views of the Tappan Zee Bridge). I cannot recommend enough doing some research in your local community around the park system or conservation—in 1979, our little lighthouse was listed on the National Register of Historic Places. Very cool all around.

By this point, hunger was setting in something fierce and we made our way along the water and south to Tarrytown. Grass Roots Kitchen is a fast casual spot right off the Tarrytown station and if I lived there, I would be at this spot every day. The menu had standard and vegan options, an enviable bakery case, and a tea selection that inspired coziness. Everything that everyone around us ordered looked delicious and I’m already planning my next trip around how many meals I can have at this singular restaurant.

As we climbed the hill into the main street of Tarrytown, we hit our second bookstore of the day—Transom Bookshop. My friend bought a special local edition of The Legend of Sleepy Hollow with an introduction by Transom Bookshop owner, Chris Steib. We decided that once we’ve read our respective non-fiction/fiction stories about the town, we can switch to read the other. I love having book friends.

We were rapidly approaching the 4:00 PM hour and many stores on main, especially on a Sunday, close around 5:00 or 6:00. We sped through the shops, checking out a very cute knitting store (Flying FIngers Yarn); a charming local giftshop (Purple Ostrich); and a pie-forward bakery (Noble Pies).

At that point, my friend had to head out but with no further plans, I decided to extend my time in Tarrytown. Shortly after we departed, I stumbled upon the very beginning of a Blessing of the Animals at Christ Episopal Church. Is there anything better than popping your head into a sanctuary and seeing dozens of cats and dogs just meowing and barking about. It was such a funny and unexpected joy jolt.

Just outside of the main stretch of stores is Pretty Funny Vintage, an antique store with quirky gifts, vintage clothing, and local classics. One of my favorite designs I saw throughout my time in the neighborhood was the headless horseman silhouette with the tagline (from the Tim Burton movie), “heads will roll.” Who doesn’t love a fun spooky season gag? Sweatshirts available in the basement.

Shops were starting to close and I was starting to feel my energy dip. I decided to regroup at Muddy Water Coffee and Cafe. I ordered a “cosmic cookie” but they also have savory items like samosas, empanadas, and quiche. As I sat with my snack, looking over my list of stops for the day and deciding my next move, I couldn’t help but notice the innate community feeling. Tucked into the corner or huddled over a table, friends were conspiring, family members were catching up, couples were giggling. It felt like a gathering space for all the things that make life beautiful. I was happy to witness it for the duration of a cookie.

My final stop of the day was My Tokyo, a Japanese restaurant suggested by my friend. I picked up some sushi to go and then made my way back to the station where my train went direct from Tarrytown to Harlem in about 35 minutes. I was home before I’d even had the chance to deep dive Zillow in the area.

Sleepy Hollow and Tarrytown were a total delight and will be added to the regular rotation of mandatory adventures. But this one was also a little bit personal. I moved to New York City in January 2016 and that fall, they offered round trip ferry rides to Sleepy Hollow for a ridiculously good deal. I was completely tickled but by the time I learned of it, schedules were full and I couldn’t find anyone with availability to go with me.

So I just… didn’t go.

“Next year,” we all said.

Except that route has never run since. And until this month, I’d never been to Sleepy Hollow. I was 22 in 2016. Perhaps it was my age or an insecurity that stopped me from making this a solo day trip. It’s one of my silliest “big regrets.”

It is funny to see how 10 years later, I have no issue doing basically anything by myself. A quiet testament to growth we don’t realize is happening. A celebration of all that we become without noticing.

Welcome to the Neighborhood:

January: Ossining, New York
February: Ridgewood, Queens
March: North Shore of Staten Island
April: Jackson Heights, Queens
May: Manhattan Perimeter
June: Yonkers, New York
July: Brighton Beach, Brooklyn
August: Crown Heights, Brooklyn
September: Bay Ridge, Brooklyn
October: Sleepy Hollow & Tarrytown, New York