Home Travel Sleepy Hollow, NY in Autumn: A Spooky and Scenic Getaway

Sleepy Hollow, NY in Autumn: A Spooky and Scenic Getaway

by Susan Pazera
Sunrise at Philipsburg Manor - Sleepy Hollow

As the leaves turn to brilliant shades of red and orange, Sleepy Hollow, New York, awakens from its summer slumber. This charming village, known for its rich history and eerie legends, becomes even more captivating in the fall. Join us on a journey through this picturesque town as we explore its iconic attractions, including Philipsburg Manor, Lyndhurst Mansion, and other hidden gems.

Philipsburg Manor: A Glimpse into Colonial History

My first stop was Philipsburg Manor, a living history museum that transports you back to colonial times. Nestled along the picturesque Pocantico River, this 18th-century farm showcases the thriving community that once thrived here. As you stroll through the meticulously restored manor house, gristmill, and barns, you’ll gain insight into the lives of early American settlers. Don’t miss the chance to witness costumed interpreters engaging in daily activities, from milling grain to blacksmithing. If you can, arrive early before the Manor opens to catch the sunrise, it’s absolutely gorgeous!

Philipsburg Manor

Philipsburg Manor

Philipsburg Manor

Philipsburg Manor

Sunrise at Philipsburg Manor - Sleepy Hollow

Sunrise at Philipsburg Manor

Woman interpreter wearing 18th century garb with traditional colonial medicines and herbal potions at the farm of historic Philipsburg Manor
Lyndhurst Mansion: A Gothic Marvel

A short drive from Philipsburg Manor lies Lyndhurst Mansion, a Gothic Revival masterpiece set amidst rolling lawns and dense woodlands. This 67-acre estate was once home to some of America’s wealthiest families, and it’s a prime example of 19th-century architecture. Wander through opulent rooms adorned with stained glass windows, elaborate woodwork, and antique furnishings. The mansion’s riverside location offers breathtaking views of the Hudson River and the surrounding fall foliage.

Lyndhurst Mansion

Lyndhurst Mansion

Lyndhurst Mansion

Lyndhurst Mansion

Lyndhurst Mansion

Lyndhurst Mansion

Lyndhurst Mansion
Grounds of Lyndhurst Mansion

Grounds of Lyndhurst Mansion


View of Mario M. Cuomo Bridge

View of Mario M. Cuomo Bridge from Lyndhurst Mansion grounds

Sleepy Hollow Cemetery: A Final Resting Place for Legends

No visit to Sleepy Hollow would be complete without a stroll through the famous Sleepy Hollow Cemetery. This serene burial ground is the eternal resting place of Washington Irving, the author of “The Legend of Sleepy Hollow.” Pay your respects at Irving’s grave and explore the captivating array of tombstones and mausoleums. The cemetery’s beauty is only heightened by the vibrant colors of autumn.

Sleepy Hollow Cemetery

Sleepy Hollow Cemetery

The grave of Washington Irving - Sleepy Hollow Cemetery

The grave of Washington Irving

Mausoleum at Sleepy Hollow Cemetery

Mausoleum at Sleepy Hollow Cemetery

Bridge on the grounds of Sleepy Hollow Cemetery
Haunting Halloween Experiences in Sleepy Hollow

For those seeking a spine-tingling thrills, be sure to check out all of the spooky season event taking place in the town. The Spirits of Sleepy Hollow Country at Philipsburg Manor, Haunted Hayrides, Lyndhurst After Dark, and the Great Jack O’ Lantern Blaze are among the many haunted attractions. The town is transformed into a terrifying realm populated by ghosts, witches, and the headless horseman himself. It’s a Halloween experience like no other, sure to send shivers down your spine.

Headless Horseman Statue - Sleepy Hollow

Headless Horseman Statue


Fall Foliage and Riverside Walks: Nature’s Beauty

While the historical sites are a major draw, don’t forget to savor the natural beauty of Sleepy Hollow in the fall. The village’s tree-lined streets and riverfront parks are perfect for leisurely walks or picnics. The changing leaves create a stunning backdrop for photos, making it an Instagram-worthy destination.

Town of Sleepy Hollow


Sleepy Hollow, New York is a place where history and folklore merge seamlessly with the beauty of autumn. From the colonial charm of Philipsburg Manor to the Gothic splendor of Lyndhurst Mansion and the eerie tales of the headless horseman, this village offers a unique blend of culture and Halloween spirit. Whether you’re a history buff, nature enthusiast, or simply looking for a spooky adventure, Sleepy Hollow beckons you to explore its fall wonders. Come and experience the magic of Sleepy Hollow in the most enchanting season of all!

Check out these other great fall destinations HERE and HERE! And for some fun fall fashion inspiration take a look HERE.

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