Day Trip to Sleepy Hollow

Headless Horseman Statue in Sleepy Hollow, NY during Fall

The town’s spooky name comes from the classic short story “The Legend of Sleepy Hollow by Washington Irving” a tale of a headless soldier turned ghostly rider after being struck by a cannonball during the Revolutionary War. Since Washington Irving and The Legend of Sleepy Hollow are so important, the town changed its name to North Tarrytown Sleepy Hollow in 1996.

This town reminds me of a smaller Salem, MA- same spooky energy. Perfect for a fall day out of the city!

Just about an hour by train from Manhattan, Tarrytown, NY / Sleepy Hollow, NY is a perfect escape for a day. Whether you’re chasing autumnal vibes, ghost-story chills, or just want a relaxing walk, good food, and historic sites. Below is a full guide, from coffee stops to cemetery strolls, designed to help you make the most of a day without a car.

GETTING AROUND

Getting from NYC to Sleepy Hollow

Getting to Sleepy Hollow is incredibly easy and budget-friendly.

  • Take the Metro-North Hudson Line from Grand Central Terminal

  • Get off at Tarrytown Station

  • Ride time: about 45–55 minutes

  • Cost: typically $15–$20 round trip

Once you arrive in Tarrytown, almost everything is walkable, including shops, restaurants, historic mansions, and even the cemetery with a scenic stroll.

Grand Central in New York, NY

THINGS TO DO

Morning: Coffee & Shopping in Tarrytown

Coffee Labs

Address: 7 Main St, Tarrytown, NY 10591

I had an iced latte with maple syrup and oat milk. It was the perfect fall drink to sip on while walking around. It does get a little crowded inside but the line moves quickly. The service is very good and if you have any questions about the menu the staff is friendly.

Next, stroll down Main Road and Beekman Ave for cute shops and restaurants. My favorite ship was The Swan’s House- a home decor store with unique vintage and new items.

Tarrytown Main Street shops in autumn

Lunch at Horsefeathers, Tarrytown

Lunch at Horsefeathers

Address: 94 N Broadway Tarrytown, NY 10591

Worth the ambience alone, it's definitely a welcomed throwback to an old pub, and you can feel that it's been there forever, in a good way. Large menu, and lots of pumpkin beers! Prices range from $10-25 depending what you get.

It’s a great place to sit down, take a break from walking, and enjoy a proper meal before heading into the historic sites.

Afternoon: Historic Sites — Philipsburg Manor & Sleepy Hollow Cemetery

While heading toward Sleepy Hollow Cemetery, walk along New Broadway Street. The locals really know how to decorate for Halloween. They are all so festive and creative.

Sleepy Hollow Cemetery

Address: 540 North Broadway, Sleepy Hollow, NY

The cemetery is about 90 acres where Washington Irving and the Rockefellers are buried in the cemetery. It is also home to Historic mausoleum, beautiful rolling hills, massive stone monuments and famous guided ghost tours in fall

The cemetery is peaceful, scenic, and surprisingly beautiful, even if you’re not visiting during Halloween season. If you time it right, joining a guided tour is absolutely worth it.

Evening: Headless Horseman Statue & Sunset Along the Hudson

Philipsburg Manor

Address: 381 North Broadway, Sleepy Hollow, NY

In 1750, the manor was a working farm that relied on the labor of 23 slaves, making the Philipses one of the largest slaveholding families in the northern colonies. With a tour, you can learn how the enslaved community maintained family networks, shared their heritage and the work they were forced to do. Tickets are $15.

Headless Horseman Sculpture

Address: 362 North Broadway, Sleepy Hollow, NY

Spend a few minutes taking a photo of the Headless Horseman Sculpture. It’s a depiction of the moment in Irving’s book when the headless horseman throws the pumpkin at Ichabod Crane. It’s on Route 9 right across from the Philipsburg Manor.

Best Time to Visit Sleepy Hollow

  • Best Overall: Late September – October (peak fall foliage + Halloween events)

  • Quietest Months: April, May, early June

  • Cold but Cozy: December for holiday charm

Fall is by far the most popular time to visit — expect crowds in October, but also the most festive experiences.

What to Wear & Bring

  • Comfortable walking shoes

  • Light jacket (even in fall afternoons)

  • Camera or phone for photos

  • Crossbody bag or backpack

  • Portable phone charger

Is Sleepy Hollow Worth a Day Trip from NYC?

Absolutely. A day trip to Sleepy Hollow from NYC is:

  • Easy to reach

  • Affordable

  • Walkable

  • Packed with history and charm

  • Perfect for fall travelers

  • Unique compared to typical NYC day trips

Whether you’re into spooky lore, colonial history, cozy cafés, or scenic river views — this destination checks every box.

Enjoy your day in Sleepy Hollow!

Jenna Willard