Sleepy Hollow is a small village situated in the town of Mount Pleasant in Westchester County, New York. This small village, often recognised as the most popular tourist destination in NY, offers Sleepy Hollow Cemetery, Headless Horseman Bridge, Lighthouse and even many attractions. Moreover, the place is the prime location of Washington Irving’s 1820’s tales named “The Legend of Sleepy Hollow”.
Located just 30 miles away from Midtown Manhattan, north of the Bronx, home too many historical sites like Old Dutch Church, Performing Art Centre and Irving’s Sunnyside. If you plan to visit Sleepy Hollow, NY, this article will exhibit more insights about the place and also make your trip more easy and memorable.
Related Search: 10 Things to Do in San Diego, California.
Things to Do in Sleepy Hollow, New York
1. Visit Famous Sleepy Hollow Cemetery
Visiting Sleepy Hollow Cemetery is one of the greatest ideas to start your trip here in Sleepy Hollow. This historical cemetery was founded in 1849, known for graves or burials of popular personalities like Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden and William Rockefeller. All these graves are depicted very clearly in “The Legend of Sleepy Hollow”. Nevertheless, the cemetery is located where it is easy to find a wooden bridge over the Pocantico River, often as the greatest photographic destination creating spooky scenes over wooden bridges.
Under cemetery’s 90 acres of lands approximately more than 47,000 tombs exist today. These interments could explore things in the Sleepy Hollow especially who are willing to take afternoon or evening guided walking tours. Open daily from 8:00 am to 4:30 pm to the general public without charging any cost. In 2009, this historical landmark was listed on the National Register of Historic Places.
2. Walk through Philipsburgh Manor
Walking leisurely around historic Philipsburg Manor is another great thing to do in Sleepy Hollow, NY. This is often known as the most thriving trading complex during the 17th and 18th century, today compassing the history of colonial American life and the history of slavery in North America. Additionally, this building exhibits enslaved millers, history of slavery and some narratives about the living history of 18th century slavery.
Spread across 52,000 acres of land, originally owned by the Anglo Dutch Philipse family, who are often considered as the wealthiest men in New York and largest slave owners in the Northern colonies in that period. This family divided this property into smaller plots such as; farmlands and enslaved Africans. At present this Philipsburgh Manor restored many things that used to demonstrate and celebrate the diversity of African and European cultures in Hudson River valley and slave garden.
Philipsburg Manor is open daily at 10 am to 4 pm except Tuesday from April 1 to October 31. Ticket cost includes $ 9 for adults and $5 for children, those who are looking at the brutality of slavery in American history.
3. Take Tour to Headless Horseman Bridge
This is the most underrated travel landmark in Sleepy Hollow, NY inspired by Irving’s story called “The Legend of Sleepy Hollow”. It is a simple wooden span that helps us to cross the Pocantico River especially during the time of 1700. This Bridge, described as the “The Legend” by Irving. Located on the east side of the Old Dutch Church, route of the Albany post and inside of the Sleepy Hollow Cemetery. At present this bridge is also called the Cemetery Bridge passing Sleepy Hollow Avenue about 0.3 miles inside of the cemetery gate.
This cemetery owns a bridge upstream of Post Road Bridge, making it a great spot to get a selfie. Even today this cemetery bridge stands as a vital connecting thing for daily funerals and mourners for those who are visiting graves. An interesting part about Headless Horseman Bridge is once depicted in films. Popular directors like Walt Disney and Tim Burton covered bridges and versions of Sleepy Hollow, including the Hudson Valley, span river border and deeper.
4. Enjoy the Sleepy Hollow Lighthouse and Scenic Hudson Riverwalk
Out of many iconic places in New York City, Tarrytown Lighthouse in Sleepy Hollow or Sleepy Hollow Lighthouse has a great legacy which once served as a half mile off shore, helping to warn ships away from dangerous depths on the east side of the Hudson river. Installed in 1883, until 1960, the lighthouse was used to maintain, but the construction of Tappan Zee Bridge erase the importance of existing lighthouse. This bridge no longer uses the lighthouse and stopped running in 1961. In 1970 Westchester County acquired the decommissioned structure from the federal government.
The Hudson River is a 315 mile river that flows from north to south and offers more stunning views and a relaxing feeling if you are willing to take cruise rides. Hudson River Adventures is a prime cruise service which offers 2 hours including sightseeing, wedding and private charters. Along with Classic Harbor Line is another popular private cruise that offers NYC’s major attractions like the Statue of Liberty from the water and is the ideal option to see New York City in a very quick way. Both day and night time tours featuring track decks, varnished mahogany rails and gleaming brass fixtures.
5. Spot Headless Horseman Sculpture
The Headless Horseman Statue is one of the most visited landmarks in Sleepy Hollow. It is an 18 foot tall sculpture chasing Ichabod Crane depicted by the local artist Linda Perlmutter and built by Bufkin Metal Fabrication. Located just away from the Sleepy Hollow Bridge, where Horseman shows how he hurled his pumpkin at Ichabod under Washington Irving’s “The Legend of Sleepy Hollow”. A total of 11 tons of steel panel makes it a great place for photographers, especially if they step into this landmark during October month, when tree leaves are turning yellow and decorated with pumpkins and hay bales.
According to some tales, a drover’s person who in the middle of last century told a horseman who appeared suddenly at a campsite, mounted on a trotting cob without a head, spoke to the animals and caused stampedes. After overlanders dreaded camping at the swamp who still believed the sight of the ghost appearing doom without a head.
6. Enjoy the Beauty of Rockefeller State Park Preserve
If you are looking for the most enchanting landmarks near Tarrytown and Sleepy Hollow, then you surely pick Rockefeller State Park Preserve. Such a mesmerising national park blessed with a natural oasis that boasts many outdoor activities like hiking or bird watching. Located in the Mount Pleasant near Sleepy Hollow and Pocantico Hills, a more elegant and incredible spot if you visit during fall foliage season when its striking rock formations, Sean Lake and Lush forest scenery are very beautiful.
Part of the Rockefeller Estate, where visitors are free to take a leisurely stroll, its 45 miles of trails follow the crushed stone carriage roads. These pathways are broad and easy for travel, adorned with charming wood and stone bridges that cross the Pocantico River. Open to the general public in 1970, recognised as the most suitable attractions are those who wish to spend leisurely hiking and pathways. Do not forget to pay $6 as a parking fee if you have a vehicle
7. Attend Great Jack O’Lantern Blaze
Experiencing the region’s most vibrant and unique festival is another enchanting thing that one must enjoy. Under the Great Jack O’Lantern Blaze around 7000 handmade carved pumpkins illuminate the historic buildings and landscapes. Hosted in Croton-on-Hudson, each pumpkin is set against the backdrop of Van Cortlandt Manor’s, an 18th century building located in the Hudson Riverside. These events are usually held during mid-September to mid-November at Van Cortlandt Manor.
While setting this massive Pumpkin’s more than 1,000 volunteers scoop, carve and light the pumpkins. Each one is synchronising lighting and original soundtrack for more unique and spooky appearances. Tickets are compulsory, visitors need to arrive 30 minutes before and you can spend 45 and 90 minutes at the event. Along with Great Jack O’Lantern Blaze festivals, Sleepy Hollow hosts events like the Museum of Pumpkin Art, the Pumpkin Carousel, the Pumpkin Windmill, and Pumpkin Planetarium.
8. Visit Old Dutch Reformed Church of Sleepy Hollow
Founded in 1685, Dutch Reformed Church is another historical evidence in Sleepy Hollow showcasing brilliant primary settings and churchyard in Washington Irving’s story. This Old Dutch church spread across 3 acres of land, majority land used for burying ground and rest of the land used as resting place for personalities like Katrina Van Tassel, Brom Bones and others in “The Legend of Sleepy Hollow”. Besides its historical significance, the church played a major centre of American folklore and tourist destination in 17 the century especially during the Halloween season.
The cemetery is the most interesting part of this Old Dutch church. The tombstones are over 300 years old, yet it offers a classic look with faded cracked tombstones under large shade trees. Taking a leisurely stroll amidst the Old Dutch country of the Hudson river valley is highly recommended, which exhibits graves of many personalities. The church reformed in 1967, served as the congregation’s home for more than 150 years, later worship on summer Sunday and special holidays extending till the 21st century.
9. Discover Local Art at Sleepy Hollow Performing Art Center
Looking to immerse yourself in local cultures and art collections to know more about Sleepy Hollow, then you need to visit Sleepy Hollow Performing Art Centre. It is a local art collection and other cultural evidence centre showcasing occasional events like dance performances, art exhibitions and cultural events. Hosted by the Sleepy Hollow High School, where high school students (its own) perform and concerts in public events like Halloween festivals and haunted hayrides. The Sleepy Hollow Halloween Show is a more popular one, it is a character from Washington Irving’s classic story which is designed to be spooky. This show highlights Headless Horseman, Ichabod Crane, who helps his friend, Katrina Van Tassle during her search.
Sleepy Hollow Performing Art Center has been consistently getting recognition from ArtsWestchester for significant contribution to the art in Westchester Country. Additionally, they have been recognised by the NY state Senate and Assembly too. Other popular events such as Oktoberfest, the Mermaid Festivals, and Halloween related events are must explore things.
10. Explore Washington Irving’s Sunnyside
The last yet beautiful spot you should visit before finishing your Sleepy Hollow trip. Washington Irving has a deep connection to this land since he is author of “The Legend of Sleepy Hollow”. Visiting Washington’s Irving’s Sunnyside or Irving’s home could be the great way to explore the neighbouring Sleepy Hollow and teen years of Irving. While Yellow Fever spread across the city, Washington Irving and his family moved to the sunny side of Hudson Valley in Tarrytown. He spent most of his adulthood here and place inspired by many sites in his famous story of Ichabod Crane and Headless Horseman.
Nestled along the banks of Hudson River is a more elegant and stylish restored home where we can spot fascinating insights about his life, work and cultural and literacy contributions. Picking the right guide will help us to learn and know how Irving designed the house and grounds showcasing his accuracy about art, nature and history under breathtaking views of Hudson River. If you are a history or art lover, looking to spend time with Sunnyside landmarks then you shouldn’t miss out on this inspiring house.
5 Best Sleepy Hollow, NY Hotels
1. Tarry Town Inn
Tarry Town Inn is a historic boutique hotel offering more elegant cozy rooms under a quaint atmosphere. Nestled in the heart of Westchester’s Hudson Valley, Tarrytown Inn contains a total of 246 guest rooms, out of that, 212 rooms exclusively made as sleeping rooms. Each room blends 19th century architectural styles with top notch amenities options like coffee makers, refrigerators and high speed internet services, multiple dining options (Cellar 49 and Goosefeather), fitness center and scenic trails. The hotel’s charming decor is inspired by the area’s history and is convenient for exploring the region’s top attractions like Sleepy Hollow Cemetery and Headless Horseman Bridge.
2. Sleepy Hollow Hotel
Sleepy Hollow Hotel is another renowned hotel in this region that boasts more spacious rooms and warm ambiance inviting guests from its facade style. Spread across 11 acres of land where grassy, tree lined grounds help visitors spend their more precious time under its tranquil beauties. The hotel includes Standard King, Standard Double, and The PatioKing, The King Balcony and Junior Deluxe Suites rooms and accommodation options. Additionally each room holds amenities like outdoor swimming pools, sauna or hot bath tube, wedding spaces, lush gardens along with panoramic river view and relaxing atmospheres. Do not miss out to taste breakfast samples like omelettes and fresh baked pastries at the hotel’s popular Bistro Z restaurant.
3. Castle Hotel and Spa
Castle Hotel and Spa is the most unique hotel when it comes to stay which offers more romantic and intimate feelings to its guests. Recommended hotel to family and couples, located at the top of the highest point in Westchester County always overlooking the Hudson River. Set in a historic castle, it offers 31 rooms and suites including suite fireplace, marble baths and 4 poster beds. Its classic architecture and scenic surroundings exhibits hotel features like spa, cozy library, American eatery and gardens in a more elegant way. If you are a budget conscious backpacker, looking for the most cost friendly hotel nearby, then choose Castle Hotel and Spa.
4. Courtyard Tarry Town
Stay under Courtyard Tarry Town allows visitors to explore local attractions and retreat to the city too. Located in Hudson Valley at Courtyard Tarrytown Westchester County, just 25 miles away from New York City. Hotels run modern guest rooms and suites with different price ranges, each one including plush bedding, ergonomic workstation, free Wi-Fi and spacious living areas. Taste culinary things like refreshing breakfast, cocktails and dinner from its Bistro, on site restaurants and bar. Spend your free time with a 24 hours fitness center, AV equipment and event venues. Located where visitors easily catch up with places like Kykuit, Lyndhurst Castle and Westchester.
5. Hampton Inn and Suites Yonkers
Close to Yonkers, and even closer to the Sleepy Hollow located just 20 minutes north of Manhattan, south of the Hudson Valley. Hampton Inn and Suites Yonkers boasts a total 150 rooms (9 rooms includes rollout showers) and 39 suites. Its 2 meeting rooms are blessed by the copy service, Wi-Fi, and easy access to the outdoor patio for breakout sessions. Despite that, the hotel is even well known for its daily hot breakfast, parking facilities, modern decor, lobby bar, indoor pool, fitness and business center.
What is the Best Time to Be There in Sleepy Hollow?
Visiting Sleepy Hollow, NY on right time is a great initial step from a backpacker if you are truly willing to enjoy its breathtaking beauty. After analysing everything and travel aspects, we came to a conclusion that visiting Sleepy Hollow is totally an individual choice. But we insist backpackers that try to be there during October month, known as a great season to enjoy its beauty. October is a very special month here since Halloween events and foliage are at their peak level. Remember place also makes a great weekend gateway any time of year.
How to Get There
Visiting Sleepy Hollow is truly an easy task, if you are an international traveller choose Westchester County Airport, located just 20 miles away. While you step out from the plane, you will get good car or cab services that help to reach Sleepy Hollow. Visitors also choose airports like LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) which come within 45 miles of distance.
Coming through Car is another popular option to reach here, backpackers need to take I-287 and Saw Mill River Parkway. If you love to travel in public transportation, choose the Metro North train which is a popular mode of public transportation, take a stop at Tarrytown station or Philipse Manor Station.
Suggested Reads: Best Places to Visit in America.
