Nestled in New York State’s Hudson Valley, just an hour drive or train ride from New York City, Sleepy Hollow, with its famous name that captivates Halloween enthusiasts, is the perfect destination for a fall weekend getaway or day trip. This charming town gives off Halloweentown vibes and is the birthplace of the Headless Horseman legend. It’s situated alongside Tarrytown, the hometown of renowned author Washington Irving, celebrated for his short story, “The Legend of Sleepy Hollow” and the lavish Rockefeller family estate, Kykuit. Sleepy Hollow truly embraces the Halloween spirit with spooky decor, weekend festivals, and parades throughout October.
Here are some must-see places to visit while you’re there:
Lyndhurst Mansion
Lyndhurst Mansion is a majestic estate and historical museum in Tarrytown where you can explore its architectural beauty and historical exhibits and soak in the breathtaking fall foliage. Guided tours start at 9:30 a.m., so if you plan on visiting Sleepy Hollow, the Lyndhurst Mansion is a perfect place to start your day!
The Armour-Stiner Octagon House
The mystical Armour-Stiner Octagon House, located in the heart of Sleepy Hollow, offers the “Myths & Mysteries” guided tour throughout October. For many years, rumors have circulated around town hinting at a mysterious connection between this enigmatic eight-sided dome and the supernatural realm. The current owners describe their encounters within its walls as experiences that transcend the ordinary. Visit the Octagon House, if you dare.
Philipsburg Manor
Philipsburg Manor is located in a picturesque setting along the Pocantico River. The scenic beauty of the property – particularly during the fall season, when the foliage is in full bloom – is reason enough to explore and enjoy nature’s beauty. The site also hosts a variety of cultural events and programs all year long, such as music performances, storytelling, and exhibitions.
Old Dutch Church and Burying Ground
The Old Dutch Church sits in a quaint area on Albany Post Road. Its 17th-century stone structure exudes an old-world charm, providing a captivating glimpse into the past. Breaking ground way back in 1685, this iconic church inspired Washington Irving’s whimsical tales. But here’s the kicker: its cemetery is the very same one where the legendary Headless Horseman is rumored to have made his ghostly appearances, so if you’re up for some spooky tales, you better be on your guard!
Washington Irving’s Sunnyside
If you’re a fan of Washington Irving’s stories, or if you simply appreciate the allure of Gothic Revival architecture, head over to Washington Irving’s Sunnyside in Irvington, located in close proximity to Sleepy Hollow. Stroll through the lush garden and wander through his home, where his writing desk and books still whisper the secrets of his creativity.
The Great Jack O’Lantern Blaze
The Great Jack O’Lantern Blaze is Sleepy Hollow’s biggest Halloween event and the best way to wrap up your trip. With over 7,000 hand-carved and illuminated pumpkins casting their warm glow around Van Cortlandt Manor’s 18th-century structures, all against the riverside landscape, you won’t want to miss it! Luckily, this event occurs throughout October and into the first few weeks of November, so you still have time to check it out.
Horseman Bagels
Horseman Bagels is a shop in Sleepy Hollow that offers a variety of delicious bagels and cream cheese spreads, including pumpkin cream cheese. Plus, they’ve got muffins, croissants, and cold-cut sandwiches.
Coffee Labs Roasters
Coffee Labs Roasters on Main Street in Tarrytown offers a selection of sustainably sourced light, medium, and dark roast coffees, each infused with notes of stewed cherry, toffee, and Brazil nut. In addition to their delectable brews, they also have a variety of pastries.
Eatarry
Located right on Tarrytown’s Main Street, Eatarry has been the go-to breakfast and brunch spot of locals and visitors alike for quite some time. Their menu features everything from pumpkin pancakes and lemon ricotta pancakes to brioche French toast, sandwiches, and even afternoon tea.