Halloween Historic Sites New York Upstate New York 

Sleepy Hollow, Tarrytown, New York

Sleepy Hollow, located in Tarrytown, New York, is a charming and historic village that is best known for its connection to Washington Irving’s classic tale, “The Legend of Sleepy Hollow.” From its historic landmarks to its seasonal celebrations, Sleepy Hollow is a must-visit destination for anyone interested in history, literature, and Halloween.

The History of Sleepy Hollow

Sleepy Hollow was originally known as North Tarrytown, but it changed its name in 1996 to honor Washington Irving’s classic story. The village has a rich history that dates back to the colonial period, and it played an important role in the American Revolution. Visitors can learn about the village’s history by visiting landmarks such as the Philipsburg Manor House and the Old Dutch Church, which both date back to the 17th century.

Celebrations held in Sleepy Hollow

One of the biggest events in Sleepy Hollow is the annual Great Jack O’Lantern Blaze, which takes place every year from September to November. The event features over 7,000 hand-carved pumpkins that are arranged in elaborate displays, including a working carousel and a 25-foot-tall Statue of Liberty. Visitors can walk through the displays and take in the spooky and whimsical sights.

Sleepy Hollow also hosts a number of Halloween-themed events throughout the season, including haunted hayrides, cemetery tours, and ghost stories. The village is home to a number of haunted attractions, such as Horseman’s Hollow, which is set in an abandoned village and features actors in period costumes, and the Sleepy Hollow Cemetery, where visitors can take a lantern-lit tour and hear tales of the village’s ghostly residents.

Halloween in Sleepy Hollow

Halloween is a particularly special time in Sleepy Hollow, as it is the setting for Washington Irving’s famous tale. Every year, the village hosts a number of events that celebrate the holiday, including the Sleepy Hollow Halloween Parade and the Sleepy Hollow Witches’ Ball. The parade features floats, marching bands, and costumed characters, while the witches’ ball is a lively dance party with live music and a costume contest.

Visitors to Sleepy Hollow during Halloween can also enjoy the Headless Horseman Hayride, a spooky nighttime adventure that takes visitors through the woods and fields of Sleepy Hollow. The ride features a cast of over 40 actors, elaborate sets and special effects, and, of course, the Headless Horseman himself.

Year Round Activities

There are plenty of things to see and do in the village year-round. Here are just a few examples:

Visit Historic Sites: Sleepy Hollow is home to a number of historic landmarks that are worth a visit, such as the Philipsburg Manor House, the Old Dutch Church, and the Sleepy Hollow Cemetery. Visitors can take guided tours of these sites to learn more about the village’s rich history.

Go on a Hike: The Rockefeller State Park Preserve is located just a few miles from Sleepy Hollow, and it offers over 1,400 acres of rolling hills, forests, and meadows to explore. The park has over 55 miles of hiking trails, ranging from easy walks to more challenging hikes.

Attend a Concert: The Tarrytown Music Hall is a beautifully restored 19th-century theater that hosts a variety of concerts, plays, and other performances throughout the year. From classical music to rock and roll, there is something for every music lover at this venue.

Take a River Cruise: The Hudson River is just a stone’s throw away from Sleepy Hollow, and there are several companies that offer river cruises throughout the year. Visitors can take in the stunning scenery of the Hudson Valley while learning about the history and ecology of the region.

Visit a Farmer’s Market: The Tarrytown and Sleepy Hollow Farmer’s Market takes place every Saturday from May through November, and it features a variety of locally grown produce, baked goods, and other artisanal products. Visitors can browse the stalls, sample some delicious food, and chat with local farmers and vendors.

Places Near Sleepy Hollow to Stay

Tarrytown House Estate on The Hudson

Baymont by Wyndham White Plains - Elmsford

Hampton Inn White Plains/Tarrytown

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