1 day itinerary for Sleepy Hallow

Itinerary

A day trip to Sleepy Hollow in early October sounds like a fantastic idea, especially with the Halloween spirit in the air! Here’s a fun and family-friendly itinerary that emphasizes nature, history, and a bit of spooky charm. Let’s get started!

Morning: Departure from NYC

8:00 AM - Catch the Train

• Start your day bright and early! Head to Grand Central Terminal and catch the Metro-North Hudson Line train to Tarrytown. The ride takes about 40 minutes, and the views along the Hudson River are simply stunning, especially with the fall foliage starting to show.

9:00 AM - Arrive in Tarrytown

• Once you arrive, it’s just a short walk or a quick taxi ride to Sleepy Hollow.

Late Morning: Explore the Great Outdoors

9:30 AM - Visit the Sleepy Hollow Cemetery

• Begin your adventure at the historic Sleepy Hollow Cemetery. This is where Washington Irving, the author of "The Legend of Sleepy Hollow," is buried. The cemetery is beautiful and serene, with lovely paths to stroll along. Keep an eye out for the famous Headless Horseman statue!

10:30 AM - Walk to the Old Dutch Church

• Just a short walk from the cemetery, you’ll find the Old Dutch Church, which dates back to 1685. It’s a picturesque spot with a rich history. Take some time to explore the grounds and snap some family photos!

Lunch: A Taste of Local Flavor

11:30 AM - Lunch at a Local Café

• Head to a nearby café or restaurant for a cozy lunch. The Horseman’s Hollow is a great option, offering delicious sandwiches and seasonal dishes. Enjoy the fall flavors!

Afternoon: Nature and History Combined

12:30 PM - Kykuit, the Rockefeller Estate

• After lunch, take a short drive or taxi to Kykuit, the stunning estate of the Rockefeller family. The gardens are beautiful, and the views of the Hudson River are breathtaking. The estate also has a fascinating history, and guided tours are available. Be sure to check if you need to book in advance!

2:30 PM - Philipsburg Manor

• Next, head to Philipsburg Manor, a historic site that offers a glimpse into 18th-century life. The grounds are lovely for a stroll, and they often have family-friendly activities, especially around Halloween. You might even catch a spooky story or two!

Late Afternoon: Embrace the Halloween Spirit

4:00 PM - Sleepy Hollow’s Halloween Attractions

• As the day winds down, check out some of the Halloween-themed attractions. The Horseman’s Hollow is a haunted experience that opens in October, and it’s perfect for families looking for a little thrill. If your kids are younger, you might want to stick to the more family-friendly options like the Legend of Sleepy Hollow walking tour, which is both educational and fun!

Evening: Wrap Up the ## Day

5:30 PM - Dinner in Sleepy Hollow

• After a day filled with adventure, enjoy dinner at a local restaurant. The Blue Hill at Stone Barns is a bit upscale but offers a unique farm-to-table experience. If you’re looking for something more casual, The Tarrytown Lighthouse has great views and a relaxed atmosphere.

7:00 PM - Head Back to NYC

• After dinner, take a leisurely stroll along the Hudson River waterfront if time allows. Then, catch the train back to NYC. The evening ride will give you a chance to reflect on your day filled with history, nature, and a touch of Halloween magic!

Tips for Your Trip:

• Dress in layers! October can be chilly, especially in the evening.
• Bring a camera to capture the beautiful fall scenery and family moments.
• Check the schedules for any special Halloween events or tours in advance.

I hope you have a spooktacular day in Sleepy Hollow! Enjoy the history, the nature, and the Halloween vibes! 🎃🍂