13 Popular Tourist Spots in Westchester! The Setting of the Sleepy Hollow Legend

When you think of Westchester, New York, you think of the setting for the legend of Sleepy Hollow, famous for the Headless Horseman. Tim Burton’s film adaptation and recent TV series have made the legend so well-known in America that few remain unaware of it.

Westchester is renowned for its cemeteries and churches featured in the tale, attracting many fans of the story as well as general tourists. In addition, Westchester offers numerous other attractions where you can interact with animals or even pick fruit—perfect for those who want to escape the city and enjoy nature. Here are 13 recommended tourist spots in Westchester.

1. Sleepy Hollow Cemetery

One of the most popular tourist attractions in Westchester is Sleepy Hollow Cemetery. Besides its legendary associations, the cemetery is the final resting place of many world-renowned figures, such as Elizabeth Arden, the founder of the American cosmetics brand; Walter Chrysler, the founder of Chrysler Corporation; and Andrew Carnegie, the industrialist who built Carnegie Hall.

During Halloween, guided “ghost tours” with lanterns are organized almost every night, making this an especially recommended time to visit.

2. Old Dutch Church

The Old Dutch Church is an old stone church built in the 17th century in Sleepy Hollow, and it is listed on the National Register of Historic Places. Although rebuilt in 1837 after a fire, it is known as the second oldest church in New York State.

Famous as the location where the Headless Horseman appears in the tale of Sleepy Hollow, it draws many fans of the legend.

3. iFLY Westchester

A rising attraction in Westchester that is popular with families is iFLY Westchester, where you can experience indoor skydiving.

All the necessary gear, including helmets and skydiving suits, is provided on-site, making it an accessible experience for first-timers. Each session lasts approximately 1 to 2 hours, with an instructor guiding you through the process. Indoor skydiving is available for ages 3 and up.

4. Union Church of Pocantico Hills

The Union Church of Pocantico Hills is a must-visit for art and culture enthusiasts in Westchester. Its stunning stained glass windows are a highlight, described by visitors as “incredibly beautiful, almost unreal for glass.”

These renowned stained glass pieces were created by two of the 20th century’s most significant artists, Henri Matisse and Marc Chagall. Matisse’s final work, a rose window, and nine exquisite pieces by Chagall are on display, accompanied by guided tours explaining their significance. This site is a must-see for fans of both artists.

5. Lyndhurst Mansion

Lyndhurst Mansion, conveniently accessible from Manhattan, attracts many tourists. Built in 1838, this mansion was once used as a retirement home by former mayors and wealthy industrialists. From its expansive backyard, you can enjoy views of the Hudson River and the Tappan Zee Bridge. Local guided tours are available in the morning and afternoon.

Visiting during the Christmas season is particularly recommended, when the mansion hosts the “Fairytale Holiday” event, adorned with decorations inspired by fairy tales like Alice in Wonderland. Photography is usually prohibited inside, but it is allowed during this special period.

6. Legoland Discovery Center Westchester

Here, you can not only view familiar Lego displays but also enjoy various attractions and rides.

At the 4D Cinema, an original movie featuring Lego characters is showcased with dynamic 3D visuals enhanced by effects like wind and scent. In “Kingdom Quest,” guests use laser guns to defeat skeleton warriors and dragons in a medieval-themed attraction, which is especially popular with young girls. A café is also available, allowing parents to relax while their children play.

7. Philipsburg Manor

Philipsburg Manor is a historic mansion built about 300 years ago by Philip, a former New York City mayor. Located near Kaiacut in a tranquil area away from the urban hustle of Manhattan, the surroundings offer a peaceful rural landscape that contrasts sharply with the bustling city.

Here, you can learn about the colonial era and the history of slavery in New York. Guided tours take you through rooms that once served as a kitchen, bedroom, and warehouse.

8. Sunnyside (Sleepy Hollow)

Sunnyside in Sleepy Hollow was the home of Washington Irving, the author of “The Legend of Sleepy Hollow.” Irving was the first internationally famous American writer, and his home attracts fans of his work from around the world.

Visitors can see the desk and books that Irving used for his writing, along with other personal artifacts. Knowledgeable guides, dressed in formal 19th-century attire, explain how Irving’s life at Sunnyside influenced his works.

9. Glen Island Park

Glen Island Park is highly recommended for visitors to Westchester. This serene park, facing the Long Island Sound, is an ideal spot to relax and take in panoramic views of the bay.

From here, you can also embark on cruises around Long Island Sound or enjoy fishing tours, making it perfect for those looking to combine leisurely walks with fun activities. It’s particularly popular during the summer season.

10. Muscoot Farm

Muscoot Farm in Westchester offers a chance to learn about traditional local farming practices, culture, and the natural environment through various interactive activities. At this farm, you can get up close with animals such as goats, cows, pigs, horses, and chickens, with friendly staff providing detailed explanations.

Numerous events, such as syrup collection and sheep shearing, are held here and are popular with both locals and visitors. A farmers’ market is also held on weekends, and during the summer, a summer camp is organized.

11. Grand Prix New York / Spins Bowl

Grand Prix New York / Spins Bowl is a multi-purpose facility where you can enjoy bowling, various other activities, and dining. It also features meeting spaces and a luxurious lounge, making it ideal for both casual fun and business events.

A highlight is the illuminated bowling alley and the expansive 10,000-square-meter car racing game, making it a popular spot for those looking for active entertainment in Westchester.

12. Wilkens Farm

Among Westchester’s many nature-based attractions, Wilkens Farm is a charming spot where you can pick apples, pumpkins, and peaches. A farmers’ market is held daily from 10 AM to 5 PM, where you can buy products such as apple pie, apple cider, donuts, cookies, and brownies made from the harvested apples.

During the season, you can even experience selecting and cutting a fir tree known for its use as a Christmas tree. This is a delightful experience for families.

13. Faraway Farm Alpacas

At Faraway Farm Alpacas, you can get acquainted with these adorable animals, known for their soft, fluffy coats and charming expressions. The farm is renowned for raising high-quality alpacas, which have won over 80 championships and more than 160 blue ribbon awards at various competitions.

If you visit Faraway Farm Alpacas, be sure to check out their handmade alpaca products, such as scarves, clothing, socks, and other accessories. These items, known for their warmth, high quality, and cuteness, make perfect gifts for Christmas or a personal treat.

◎Summary

Westchester is famously known as the setting of the Sleepy Hollow legend, but it offers much more—from nature-based attractions to a variety of activities that allow you to immerse yourself in the outdoors. For Westchester, the Halloween and Christmas seasons are especially recommended. Be sure to visit the charming town of Westchester in the New York suburbs to experience its unique attractions.

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