Fall under the spell of Sleepy Hollow, New York! Famous as the backdrop of Washington Irving’s 1820 tale The Legend of Sleepy Hollow—featuring Ichabod Crane and the eerie Headless Horseman—this Hudson Valley town enchants today with scenic views, seasonal festivities and lively farmers markets.

Grab a bite at Horsefeathers

Start with a tasty stop at Horsefeathers in nearby Tarrytown. This charming colonial-style eatery dishes up comfort food favorites—think sandwiches, roast turkey, seafood and more—often with playful names. Don’t miss the Ichabod Cod, Englebert Pumperdink or John Paulding.

Take a spooky tour after dark

As night descends, set out on a two-hour guided lantern tour through historic Sleepy Hollow Cemetery. As you explore the 90-acre grounds, you’ll uncover local secrets while admiring intriguing symbols, haunting stories and artful monuments. It’s the perfect way to feel the legend come to life.

Life

6 Cozy & Fun Things To Do in Gatlinburg, Tennessee This Fall

Appreciate autumn’s glory in Gatlinburg! Nicknamed the “Gateway to the Smoky Mountains,” this resort city is known not only for its stunning views but also for miles of trails, sightseeing tours and a thriving town center. Ride, zipline and more fun at Anakeesta Kick off your day full of adventure at Anakeesta, an award-winning amusement […]

Visit Kykuit, the Rockefeller Estate 

The 40-room residence, also home to gardens, has housed four generations of the wealthy family. 

Have festive fun at the Great Jack O’Lantern Blaze

The annual event features seasonal displays and thousands of carved pumpkins.

Admire the sunrise over the New Croton Dam 

The 301-foot-tall dam, located in Westchester County, was completed in 1906.

Food

Great Wolf Lodge’s New Halloween Menu is Scary-Good—Here’s What to Try

Missing the carefree fun of summer now that fall has arrived? Great Wolf Lodge has you covered. With 22 locations across the U.S.—from the Pocono Mountains to Traverse City, Michigan—America’s largest indoor water park resort keeps the splashy fun going all year long. And this season, there’s an extra reason to visit: a limited-time Howl-O-Ween […]

Bonus: Celebrate the Sleepy Hollow spookiness at home!

Sip a tasty spicy cocktail inspired by the nearby Sweet Grass Grill in Tarrytown and cozy up with the iconic short story set in Sleepy Hollow 

Bloody Mary

Ingredients:

• 32 oz. vegetable juice
• 1 cup vodka
• 3 Tbs. Worcestershire sauce
• 3 Tbs. lemon juice
• 2 tsp. celery salt
• 1 tsp. black pepper

Mix all ingredients in a pitcher. Pour into ice-filled glasses rimmed with lemon juice and salt, then garnish with olives and celery sticks. Serves 8. 

Book to read: The Legend of Sleepy Hollow by Washington Irving 

In this eerie classic, schoolteacher Ichabod Crane learns the legend of a headless rider is no mere folktale when a shadowy figure stalks him through haunted woods.

This story first appeared in the October 20, 2025, print issue of Woman’s World magazine.

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