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Life

Sleepy Hollow: Where Every Day Feels Like Halloween

Kaytie Jimenez
This article is written by a student writer from the Her Campus at Pace chapter.

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.

Kaytie Jimenez is a senior at Pace University's New York City campus. She has been a member of Her Campus Pace since the fall of 2022. Beyond her involvement with Her Campus, Kaytie distinguishes herself in the digital realm, where she curates captivating content on her Tik Tok platform, encompassing diverse themes, from the world of fashion to acting, as well as her profound affinity for the beloved television series, "The Vampire Diaries." Her influence has reached over 12,000 followers. Notably, her influence extends beyond mere entertainment, as she has engaged in collaborations with brands like Capsul Jewelry and Just4Kira Contact Lenses. These collaborations have witnessed her masterfully crafting user-generated content to zealously endorse their products. Kaytie is also an office assistant at KAVE Tax & Business Consultants LLC. Her responsibilities encompass overseeing the company's Instagram account, recording the company’s profits and expenses, and proficiently managing file archives. Within the academic sphere, Kaytie is majoring in international business management and minoring in finance. Her educational pursuits are testament to her dedication to intellectual growth and professional acumen. During her free-time, Kaytie indulges in a myriad of activities such as playing the piano, reading, journaling, and traveling. Furthermore, she enthusiastically shares her fashionable insights and travel adventures through Pinterest, showcasing her sense of style and wanderlust. Last but certainly not least, her Colombian heritage endows her with an encyclopedic knowledge on coffee and has an unwavering passion for “The Vampire Diaries.”