Best Attractions to Visit in Sleepy Hollow NY

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Up the Highway and Over the Bridge

The leaves on the trees are bursting with beautiful colors of orange, red, and yellow. Fall is my favorite time of the year. Going on hikes, capturing photos of the amazing foliage, and getting into the spirit of Halloween. I always loved Halloween as a kid. Dressing up and watching scary movies was something I looked forward to each year. It was time to plan my next road trip.

During my search, I came across an article about Sleepy Hollow. To my amazement, I didn’t realize it was an actual 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 if you live in New England, New York, New Jersey, or the Pennsylvania area.

I’m lucky to live in the middle of so many cool places. I made plans with my friend FeFe who travels locally and abroad. She will show you how to travel and save on some awesome vacations. 

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

I dislike going places and driving all over the place in circles. It was a straight drive up the highway and over the Governor Mario Cuomo Bridge. Driving over the Hudson River was beautiful. I felt like taking out a paintbrush and doing a Bob Ross painting. I hear him in my head, “I’m going to add a little yellow and some reds and stroke the greens evenly. Bob Ross was an amazing painter. 

Legends and Myths of Sleepy Hollow and Tarrytown

For some who have not read the famous book written by Washington Irving, “The Legend of Sleepy Hollow” was published in 1819. It was a story about the Headless Horseman, believed to be a Hessian soldier who was decapitated by a cannonball in battle. The story has been retold with plays, movies, and cartoons. I have never read the book, but I may do this one day. Books are always better than movies. The story is set in 1790 Tarry Town, now known as Tarrytown, NY.

If you want to know more about this intriguing love story or the mystery of the disappearance of Ichabod Crane. Read the quick summary, or grab the book from your local library or YouTube. For the Legend of Sleepy Hollow. Washington Irving is buried at the Sleepy Hollow Cemetery.

“And he would have passed a pleasant life of it, in despite of the Devil and all his works, if his path had not been crossed by a being that causes more perplexity to mortal man than ghosts, goblins, and the whole race of witches put together, and that was—a woman.”

— Washington Irving, “The Legend of Sleepy Hollow

Sleepy Hollow’s Spell

When I travel, I like to dig deep into history. I like to know who were the previous settlers before the European arrival. The area known as Sleepy Hollow was first inhabited by Native Americans, part of the Weckquaesgeek and Sintsinct tribes. During the winter, they moved inland to seek shelter against the harsh winds and snow. The first white settlers came to the area in the 1600s after the voyage of Henry Hudson. There are many stories of supernatural occurrences that surround Sleepy Hollow and Tarrytown.

When I was in town, I didn’t feel any creepy or”sleepy” feeling that this town was haunted. There is a story of a Native American who casts a spell, and anyone who walks along the Hudson River becomes drowsy. This is where the name Sleepy Hollow comes from. It actually 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 an extremely scary time. I think about how I use 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 and not being outcasted as witches.

The story is not the same for Ms. Hulda. After reading the story about her bravery and caring heart in trying to help her local villagers, it 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 a herbalist, she was called a witch. Ms. Hulda was ready to fight during the Revolutionary War; she was killed by British troops. Her body was found and buried in an unmarked grave at Old Dutch Burying Ground. In 2019, Ms. Hulda was given a proper burial and 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 PASS/ $10 per person/ Members get in free!/ BUY TICKETS

Madame C. J. Walker

 ‘No woman of her race could afford such a place.’”the New York Times wrote. Madam C.J. Walker was born Sarah Breedlove in 1867 to formerly enslaved parents. In 1917. the 20,000 square foot, 34-room Italianate mansion was completed on Villa Lewaro, Irvington, NY 10533. Designer Vertner Tandy was the first African American architect registered in New York. Her mansion sat next to the most prominent men, including 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 extremely Recommended. You will not be let on the property without a tour ticket. 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 there is even a ghost story. Once again, due to the Halloween holiday, most places are sold out.

Sleepy Hollow Cemetery and Sleepy Hollow Bridge

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

Who would think about visiting a cemetery? I would. Sleepy Hollow Cemetery has centuries of famous people buried here, ghost stories swirling around the grounds, and is a local attraction all year. A week before Halloween, it was so crowded that it was barely anywhere to park. People were visiting, admiring, and paying respect to those buried at their last resting place. People on walking tours or people like me who are fascinated by tombstones from centuries ago.

Tours and events are held here throughout the year. There are some monuments and headstones that 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 Sleepy Hollow Avenue, about 0.3 miles inside the cemetery’s south gate. You will find Sleepy Hollow Bridge. The bridge is becoming worn; this is something I hope to be preserved as it’s famous for the story of Ichabod Crane. Who leads the Headless Horseman on a horseback chase through the woods, and he’s finally caught at the foot of a wooden bridge that stretches over 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 came to find out, through driving through the village of Sleepy Hollow and Tarrytown, you will see several statues depicting the headless horseman.

Ending the day with some good food

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

More Great Places to Visit in Sleepy Hollow and Tarrytown NY

Check out this amazing 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 be back in the quiet Villages of Sleepy Hollow and Tarrytown. I recommend visiting off-peak holiday seasons or purchasing tickets early in advance to see all the great attractions. 

Places I want to Visit when I Return

• 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

Until next time… To my explorers, historians, photography enthusiasts, and adventure seekers. Check out my Youtube video and subscribe to my channel.