Looking for haunted history, river views, and timeless legends? Head to Sleepy Hollow! This Hudson Valley village is steeped in folklore, historic estates, and spooky charm. Whether you're tracing the footsteps of the Headless Horseman or exploring scenic trails, Sleepy Hollow makes for a magical escape just outside NYC.
Sleepy Hollow, NY Highlights:
- For Adventurous Travelers: Hike Rockefeller State Park Preserve – Trek rolling hills, carriage roads, and forested trails with panoramic views.
- For History Buffs: Explore Philipsburg Manor – Step back to the 1700s with costumed interpreters and hands-on colonial history.
- For Shoppers: Browse Tarrytown’s charming Main Street – Just next door, enjoy unique shops, antiques, and boutiques in a walkable downtown.
- For Couples: Walk the scenic Old Croton Aqueduct Trail – Stroll hand-in-hand on a peaceful path past estates, woods, and river views.
- For Families: Visit the Headless Horseman statue and Sleepy Hollow Cemetery – Take a not-too-scary tour of spooky landmarks and literary legends.
Best Time to Visit Sleepy Hollow, NY
The best time to visit Sleepy Hollow is in October, when the village transforms into a Halloween haven with haunted tours, fall festivals, and fiery pumpkins. Spring and summer also offer pleasant weather for hiking, river views, and historical sightseeing.
How to Get to Sleepy Hollow, NY
- If you are traveling by car: Sleepy Hollow is just off U.S. Route 9 and about 45 minutes north of New York City.
- By Train: Take the Metro-North Hudson Line from Grand Central to Tarrytown Station (5 minutes from Sleepy Hollow).
- By Bus: Westchester Bee-Line buses serve the area from other Westchester County towns.
Where to Stay in Sleepy Hollow, NY
- Castle Hotel & Spa – Luxurious hilltop escape in nearby Tarrytown with spa services and romantic views.
- Tarrytown House Estate – Historic mansion hotel with Hudson River views and modern amenities.
- SpringHill Suites by Marriott – Comfortable and family-friendly option minutes from Sleepy Hollow sites.
Best Things to Do in Sleepy Hollow, NY
1. Kykuit
Rating: ★★★★★
Kykuit is also known as the John D. Rockefeller Estate. It is comprised of a 40-room mansion which was built for the oil tycoon and his family between 1907 and 1913, and enjoys sweeping views of the Hudson River Valley.
The four storey Georgian Classic Revival mansion’s interior was designed by Ogden Codman Jr. and features a remarkable collection of ceramics from China and Europe as well as priceless antiques, fine 20th century art and wonderful vintage cars.
The impressive mansion is surrounded by formal gardens in the Beaux Arts style and includes several statues and themed gardens like the Morning Garden, Japanese Tea Garden and more. Entrance to the historic estate is by guided tour only.
Address: Kykuit, 381 N. Broadway, Sleepy Hollow, NY 10591, Phone: 914-366-6900
2. Sleepy Hollow Cemetery
Listed in the National Register of History Places and 2009, Sleepy Hollow Cemetery is the final resting place of several famous people. The 85-acre cemetery first opened in 1849 and was then called the Tarrytown Cemetery.
Sleepy Hollow Cemetery is carefully tended and all the old monuments and gravestones are kept in a good state of repair, as befits the last resting place of famous people such as William Rockefeller, Andrew Carnegie, Walter Chrysler, Elizabeth Arden, Leona Helmsley, Samuel Gompers, Brooke Astor and Washington Irving. The best way to learn all about the cemetery is to join one of their guided walking tours.
Address: Sleepy Hollow Cemetery, 540 North Broadway, Sleepy Hollow, NY 10591, Phone: 914-631-0081
3. The Old Dutch Church and Burial Ground
The Old Dutch Church and Burial Ground of Sleepy Hollow is one of the oldest religious buildings in New York State. The 17th century stone church was completed around 1699 and was built by Frederick Philipse I, a wealthy merchant and, ironically, a slave-trader. The ancient building is still used for religious services from May to September and for special services at Christmas, but was designated a National Historic Landmark in 1961.
Adjacent to the church you will find an ancient burial ground which features in Washington Irving’s book “The Legend of Sleepy Hollow”. Legend has it that the peaceful burial ground is haunted by a headless horseman. Visitors are welcome to tour the church and cemetery on a self-guided walking tour.
Address: The Old Dutch Church, 430 N. Broadway, Sleepy Hollow, NY 10591, Phone: 914-631-4497
What to do if you are traveling with kids:
4. Philipsburg Manor
Philipsburg Manor was once part of a 52,000 acre estate owned by Dutch immigrant Frederick Philipse, who used the manor house as part of an extensive commercial complex operated mainly by enslaved Africans and tenant farmers from various parts of Europe. Today visitors can take a step back in time to 1750 as they tour this working museum.
The Manor House is filled with 17th and 18th century antiques and period furnishings and you can see a working water-powered grist mill and millpond. Costumed docents bring the history to life. Highlights include the slave garden, and a reconstructed tenant farm house. The house is rumored to be haunted and the manor hosts a “spirited” annual Halloween Ghost Tour.
Address: Philipsburg Manor, 381 N. Broadway, Sleepy Hollow, NY 10591, Phone: 914-366-6900
5. Rockwood Hall State Park
Rockwood Hall State Park forms part of the Rockefeller State Park. Originally this large tract of land was home to Rockwood Hall, one of the largest private homes in the U.S. The property was then owned by oil magnet William Rockefeller, brother of John D. Rockefeller.
In 1946 the impressive manor house and all the outbuildings were razed to the ground following foreclosure by the bank. Care was taken to preserve the beautiful gardens which boasted hills, woodlands and meadows. Today the park is open to the public for walking/hiking along miles of well-maintained trails, many of which offer outstanding views of the Hudson River.
Address: Rockwood Hall State Park, Phelps Way, Pleasantville, NY 10570
If you are a photographer, don't miss:
6. Kingsland Point Park
You will find the Kingsland Point Park at the mouth of the Pocantico River in the village of Sleepy Hollow. The 18-acre park stretches along the shore of the Hudson River, where it provides a much-loved outdoor recreation area. The park is home to various playing fields for soccer/lacrosse as well as a playground area for younger children to enjoy. There are 2 picnic areas with covered pavilions which can be hired for parties. Other amenities include a dog park, kayak tours and restrooms. You will also be able to visit the historic lighthouse – Tarrytown Light - guided tours are available in summer.
Address: Kingsland Point Path, Sleepy Hollow, NY 10591, 914 366 5109
Activities and Attractions for Couples and Singles:
7. Patriot’s Park
Patriot’s Park is tucked away on Broadway, on the border between Tarrytown and Sleepy Hollow, where it hosts a very popular Farmer’s Market every Saturday from May to October. In addition to visiting the market, people come to the park to use the basket ball court and the children’s playground. The park covers a modest 4 acres but is a popular destination for community events all year round. You can take a pleasant stroll along the paved walkway to admire a variety of monuments which relate to the historic capture of a British spy on this spot. There are plenty of shady spots to stop for a picnic.
Address: Broadway, Sleepy Hollow, NY 10591
8. Headless Horseman Statue
Commemorating the “Legend of Sleepy Hollow”, from the famous literary work by Washington Irving, the headless horseman statue is a prominent landmark in Sleepy Hollow. Visitors will find this impressive public artwork on the Route 9 median, between Philipsburg Manor and the Old Dutch Church. The 18-foot tall sculpture was designed by local artist Linda Perlmutter and built by Milgo Bufkin Metal Fabrication, using a massive 11 tons of steel. To say that it is impressive is a total understatement. The Headless Horseman Statue depicts the character Ichabod Crane fleeing for his life from the infamous headless horseman and is a popular spot for visitors to take photo souvenirs of their visit to Sleepy Hollow.
Address: 362 North Broadway, Sleepy Hollow, NY 10591
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