Sleepy Hollow, New York - Founded in 1640

Sleepy Hollow is a charming and historic village in New York's Hudson Valley, located about 20 miles north of New York City. The ghostly village is best known as the setting of Washington Irving’s “The Legend of Sleepy Hollow.” More than 200 years later, the story remains one of the most famous ghost tales in American folklore — remade in many versions and translated into dozens of languages.

The author Washington Irving achieved global recognition thanks to this tale, and became one of the first American writers to gain an international reputation. Washington Irving is also known for writing "Rip Van Winkle." These two short stories, both published in "The Sketch Book," are among Irving's most enduring works. 

In 1609, the two square miles comprising the village of Sleepy Hollow belonged to the Weckquaesgeck tribe. This Native American tribe is variously described as a Delaware Tribe or a Mohican Tribe, or perhaps some mix of the two. During the early days of New Netherlands, relations between the tribe and Dutch settlers were relatively peaceful, but by 1643 the Dutch were at war with the Weckquaesgeck and several other regional tribes.

Today, Sleepy Hollow is home to several historic sites and landmarks. One of the most notable is the Sleepy Hollow Cemetery, where Washington Irving, as well as other prominent figures such as Andrew Carnegie, William Rockefeller, and Elizabeth Arden, are buried. Visitors can explore the cemetery on guided tours and learn about its history and notable residents. There is also the Old Dutch Church which is the oldest church in New York State.

Sleepy Hollow is often listed as a top spot for Halloween season getaways and to see fall foliage. Defying the passage of time, this magical area has managed to preserve much of the history and natural beauty which have always drawn people to it.

In addition to its great history and fabulous legends, the village offers a wide variety of outdoor adventures and activities. The village offers parks, forests, rivers, lakes, streams and trails along one of the most scenic stretches of the Hudson River—ideal for trout fishing, horseback riding, biking, boating, hiking, or simply escaping into the woodlands of Sleepy Hollow.

Given its association with the Headless Horseman legend, Sleepy Hollow embraces its spooky reputation and hosts various Halloween events and celebrations throughout the month of October. These include haunted hayrides, cemetery tours, storytelling sessions, and other seasonal activities that attract visitors looking for a festive and atmospheric experience.

The town was called North Tarrytown until 1996 when the village voted to rename it Sleepy Hollow. Many people who visit Sleepy Hollow also visit its neighbor, Tarrytown which gets into the Halloween spirit. The Hudson Valley, which includes Sleepy Hollow, was named on Time's list of the world's 100 greatest places in 2021.

The autumn months bring stunning fall colors along the Hudson River, attracting photographers and nature lovers. Scenic drives and hikes are popular during this time. While not as well-known for winter sports, nearby areas provide opportunities for skiing and snowboarding. The village itself becomes picturesque with holiday decorations and events.

Sleepy Hollow attracts visitors from near and far who are drawn to its charming atmosphere, rich history, and connection to the famous legend. It offers a blend of natural beauty, cultural heritage, and a touch of mystery, making it a captivating destination for Halloween lovers, history enthusiasts, literature lovers, and those seeking a tranquil retreat.