The advent of spooky season brings endless options for driving-distance getaways packed with U-pick orchards, twisting corn mazes, and high-tech haunts. But only Sleepy Hollow, at the gateway to New York’s Hudson Valley, has a reputation so perfectly tied to the macabre.

As the setting for Washington Irving’s “The Legend of Sleepy Hollow,” the town and its neighboring villages blend American history, small-town autumn charm, and an enduring flair for the supernatural. It’s about a two and a half hours drive from Philly — or take Amtrak to Penn Station, get to Grand Central, and hop on Metro-North’s Hudson Line.

Once you’ve arrived, the mix of colonial history, Halloween pageantry, and riverfront beauty makes it easy to fall under Sleepy Hollow’s spell.

Stay: Tarrytown House Estate

If you’re making a weekend of it, check into Tarrytown House Estate, a historic retreat on a hill above Sunnyside. The estate is home to Goosefeather, Chef Dale Talde’s acclaimed Cantonese-inspired restaurant, and combines classic mansions with modern touches — think terraces, fire pits, and lounges. It’s one of the few local hotels that’s both stylish and (relatively) affordable. During fall, the property leans into the season with festive touches like pumpkin displays and glowing jack-o’-lanterns scattered across the grounds. It’s an ideal base for exploring Sleepy Hollow’s haunted happenings — close to the action, but tucked away once the lanterns dim.

📍 49 E. Sunnyside Ln., Tarrytown, N.Y. 10591

Snack: Irvington Station

However you choose to travel, make a morning pit stop at Irvington station. Grab a matcha latte or flat white from the Australian-accented Ludy Café, and a sage-scented apple-cheddar scone from Red Barn Bakery, walking distance from one another right along the train tracks.

📍 Ludy Café, 7 N. Astor St., Irvington, N.Y. 10533

📍 Red Barn Bakery, 4 S. Astor St., Irvington, N.Y. 10533

Learn: Blue Hill at Stone Barns

Continuing north, head into the woods of Tarrytown to chef Dan Barber’s famous Blue Hill at Stone Barns for a guided Explore Tour of their elysian farm and agricultural center. Take a spin through the market, admiring the hand-thrown ceramics and exquisite preserves, and stay for lunch the cafeteria. Reservations required.

📍 630 Bedford Rd., Tarrytown, N.Y. 10591

Stroll: Sleepy Hollow Cemetery

After arriving in Sleepy Hollow proper, ease into the spookiness at Sleepy Hollow Cemetery, where the one-hour guided tour (in full daylight) leans more history than horror. Not only is the cemetery beautiful, it’s also a great context-setter for the region, providing all the background on its most famous storyteller, Washington Irving, who rests here among other notable figures.

📍 540 N. Broadway, Sleepy Hollow, N.Y. 10591

Solve: The Headless Horseman Files

At The Headless Horseman Files, collect clues from costumed townspeople to unravel what really happened to Ichabod Crane. This live theater — meets — interactive whodunit at Philipsburg Manor is part mystery, part museum experience — and yes, you can exit through the gift shop for a Horseman snow globe.

📍 381 N. Broadway, Sleepy Hollow, N.Y. 10591

Vibe: Lyndhurst After Dark

Bask in the flickering glow of candles and Gothic drama at the Lyndhurst After Dark, the spooky (but not scary) experience at the Lyndhurst Mansion. Guests walk through the riverfront estate, decked in its Halloween best, and encounter live actors in period dress, who share unnerving tales of the mansion’s history.

📅 Oct. 16—26 (recommended for kids 10+)

📍 635 S. Broadway, Tarrytown, N.Y. 10591

Dine: Goosefeather

Potstickers plumped with dry-aged beef, char siu Berkshire pork belly and blueberry cheesecake mochi waffles grace the menu at Goosefeather. The free-spirited Cantonese-ish joint comes from Dale Talde, known for his appearances on Top Chef.

📍 49 E. Sunnyside Ln., Tarrytown, N.Y. 10591