Best Attractions to Visit in Sleepy Hollow NY

Trip to Sleepy Hollow

Sleepy Hollow offers numerous attractions that make it a perfect fall getaway. One of the must-see spots is the Old Dutch Church, famously associated with Washington Irving’s “The Legend of Sleepy Hollow.” The churchyard is stunning in autumn and offers a glimpse into the town’s history. Nearby, you can explore the Sleepy Hollow Cemetery, where you can pay your respects to Irving himself and see the graves of other notable figures.

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Another highlight is Philipsburg Manor, an 18th-century estate with beautiful grounds and informative tours. In the fall, they often host special events celebrating the season. Don’t forget to enjoy a scenic walk along the Tarrytown Lakes, where the vibrant colors of the foliage reflect beautifully on the water.

Be sure to check out the Halloween festivities, especially if you visit in October. The town offers haunted hayrides and spooky storytelling that truly embody the spirit of Halloween. With its charming attractions and rich history, Sleepy Hollow is the perfect destination to enjoy the fall season!

During my search, I came across an article about Sleepy Hollow. To my amazement, I hadn’t realized it was a real place. I was an hour away from Sleepy Hollow, NY—the famous Legend of the Headless Horseman. A visit to Sleepy Hollow, NY, is a fun day or overnight road trip for those living in New England, New York, New Jersey, or Pennsylvania.

I’m fortunate to live in the midst of so many wonderful places. I made plans with my friend FeFe, who travels locally and abroad. She will show you how to travel and save on some incredible vacations. 

I’m someone who likes to stay organized. We both made lists of the places we wanted to visit. I went to Google and checked for updates on admission prices, whether reservations were required, and to see pictures from people who had recently visited.  I typed all the destinations into the MapQuest route planner and got a list of directions in order.

It was a straightforward drive up the highway, crossing over the Governor Mario Cuomo Bridge. The view of the Hudson River was beautiful, and I felt inspired to take out a paintbrush and create a painting like Bob Ross would. I could almost hear him saying, “I’m going to add a little yellow and some reds, and stroke the greens evenly.“ Bob Ross was truly an amazing painter.

 

Legends and Myths of Sleepy Hollow and Tarrytown

For those unfamiliar with it, “The Legend of Sleepy Hollow,” written by Washington Irving, was published in 1820. The story revolves around the Headless Horseman, a ghost who is believed to be a Hessian soldier decapitated by a cannonball during battle. This tale has been adapted into numerous plays, movies, and cartoons. Although I have not yet read the book, I may do so someday, as I believe books are always better than their movie adaptations. The story is set in Tarry Town, now known as Tarrytown, NY, in the year 1790.

It is important to mention that Washington Irving is buried in Sleepy Hollow Cemetery.

When I travel, I enjoy delving into history. I would like to know who the previous settlers were before the arrival of Europeans. The area was first inhabited by Native Americans, specifically members of the Weckquaesgeek and Sintsinct tribes, in what is now Sleepy Hollow.

During the winter, they moved inland to seek shelter against the harsh winds and snow. The first white settlers arrived in the area in the 1600s following Henry Hudson’s voyage. There are many stories of supernatural occurrences that surround Sleepy Hollow and Tarrytown.

I didn’t feel any creepy or”sleepy” feeling that this town was haunted when I was in town. There is a story of a Native American who casts a spell that makes anyone who walks along the Hudson River drowsy. This is where the name Sleepy Hollow comes from. It felt peaceful, with a serene atmosphere. Maybe the spell doesn’t work on me. This is a beautiful town with a lot of history.

Hulda, the Witch

During the 18th and 19th cen­turies, towns­peo­ple were very su­per­sti­tious, and any­one who was dif­fer­ent was con­sid­ered to be a witch. This was a terrifying time. I often reflect on how I utilize natural herbs and essential oils for healing, and if I were there during that time, the odds would be against me. Times have changed, and people are turning to more natural remedies without fear of being ostracized as witches.

The story is not the same for Ms. Hulda. Reading about her bravery and caring heart in trying to help her local villagers saddened me. All she wanted was to help the sick and those in need. She lived alone in the woods, and what is now known as an herbalist, she was called a witch.

Ms. Hulda was ready to fight during the Revolutionary War; British troops killed her. Her body was found and buried in an unmarked grave at Old Dutch Burying Ground. In 2019, Ms. Hulda received a proper burial and was acknowledged for her bravery and sacrifice. When I read this, it warmed my heart. To be recognized, I hope she is now resting in peace.

The Best Places to Visit

 

Lyndhurst Mansion 

Address: 635 S Broadway, Tarrytown, NY 10591/(914) 631-4481

Timed Tour Tickets may be purchased here. EVERY DAY, MAY 3RD – NOVEMBER 24TH: 9:30 AM – 4:30 PM (LAST ENTRY AT 3:00 PM. Daily Ground Pass: $10 per person. Members get in free!/ BUY TICKETS

I love architecture, and as you may have read in my previous blog, I have a particular fondness for castles. When we entered the welcome center, I noticed a picture of a man. I said, he looks so familiar. I wasn’t sure if I was correct, but I thought it was Barnabas Collins and  Angelique from the TV show Dark Shadows. It was true indeed, the characters. I used to watch this show when I was a little girl.

Lyndhurst was the set for the movies House of Dark Shadows (1970) and Night of Dark Shadows (1971). The mansion sits on 67 acres beside the Hudson River in Tarrytown, NY. Tickets were sold out for the mansion tour, but you can still visit the grounds for some exploring for $10. We spent almost two hours here. The scenery, featuring fall foliage, a bridge, and a castle-like mansion, was incredible.

 

 

 

Madame C. J. Walker

 ‘No woman of her race could afford such a place.’”The New York Times reported that Madam C.J. Walker was born Sarah Breedlove in 1867 to parents who were formerly enslaved. The 20,000 square foot, 34-room Italianate mansion was completed on Villa Lewaro, Irvington, NY 10533. Vertner Tandy was the first African American architect registered in New York. Her mansion sat next to the most prominent men, John D. Rockefeller and Jay Gould. 

Madame C.J. Walker was the first female self-made billionaire. She wanted black people to know they could achieve anything they wanted and be entrepreneurs. The mansion is not open to the public and is owned by Madam C.J. Walker’s great-great-granddaughter, A’Lelia Bundles.

Check out this Virtual Tour of the exquisite mansion.

The Armour Stiner Octagon House

Address: 45 W Clinton Ave, Irvington, NY 10533/ (914) 817-5763

Tickets Purchased Online are highly recommended. You will not be allowed on the property without a tour ticket, and parking is limited. The Armour Stiner Octagon House is a private residence, and tours are only allowed at certain times and days. Please visit their website to purchase tickets. This house holds amazing stories, from its architecture to the people who once lived here, and it even has a ghost story. Once again, due to Halloween, most places are sold out.

Sleepy Hollow Cemetery and Sleepy Hollow Bridge

Address: 540 N Broadway, Sleepy Hollow, NY 10591 (914) 631-0081

Who would consider visiting a cemetery? I would. Sleepy Hollow Cemetery is home to the graves of centuries of famous individuals, with ghost stories surrounding the grounds, making it a year-round local attraction. A week before Halloween, the area was so crowded that parking was nearly impossible to find. People were visiting to admire and pay their respects to those buried in their final resting places, including those on guided tours and individuals like me who are fascinated by tombstones from centuries past.

Tours and events are held here throughout the year. Some monuments and headstones were creatively built. Famous burials include Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller.

 

If you head down the driveway on Cemetery Road, toward Sleepy Hollow Avenue, you will find Sleepy Hollow Bridge about 0.3 miles inside the cemetery’s south gate. Although the bridge is showing signs of wear, I hope to preserve it because it is famous for the story of Ichabod Crane. In the tale, Ichabod is pursued by the Headless Horseman on a horseback chase through the woods, and he is ultimately caught at the foot of a wooden bridge that spans the Pocantico River.

Sleepy Hollow Sculpture

Address: 420 N. Broadway, Sleepy Hollow, NY

This is a roadside attraction a few feet from Sleepy Hollow Cemetery. It’s on the east side of US Hwy 9/N. Broadway, just north of the bridge and south of the Old Dutch Church, at the entrance to Sleepy Hollow Cemetery. As I discovered, driving through the villages of Sleepy Hollow and Tarrytown reveals several statues depicting the Headless Horseman.

 

Ending the day with some good food

We visited Guadalajara Mexican Restaurant at 2 Union Street, Briarcliff Manor, NY 10510. We enjoyed our food, had a good conversation about our day, and the customer service was excellent.

More Great Places to Visit in Sleepy Hollow and Tarrytown, NY

Check out this fantastic page for a complete list of what to see, where to stay, and where to eat! Visit Sleepy Hollow. When the Halloween tourists leave, I will return to the quiet Villages of Sleepy Hollow and Tarrytown. I recommend visiting off-peak holiday seasons or purchasing tickets in advance to see all the great attractions. 

Additional places to visit

• Madam C.J. Walker’s mansion
• Kykuit
• The Armour-Stiner (Octagon) House
• The Sleepy Hollow Lighthouse (aka Tarrytown Lighthouse and Kingsland Point Lighthouse) 
•  Great Jack O’Lantern Blaze 
• Hulda: A production of the Old Dutch Church

 

Before you plan your next getaway, take a moment to explore within.

My book, Let Yourself Bloom: Affirmations to Nourish Your Spirit, along with its accompanying guided journal and coffee table edition, was created to inspire courage, curiosity, and self-belief—no matter where life takes you. The journey starts with one choice: to live fully and fearlessly. 🌍

Discover your next source of inspiration here 👉