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Tarrytown, Sleepy Hollow, Irvington - TravelStorys

Tarrytown, Sleepy Hollow, Irvington

Location Trip Time Travel Type
New York 3 hours

Discover All Tarrytown, Sleepy Hollow, and Irvington Have to Offer

Tour Excerpts

About this Tour

As you walk through three Cuomo Bridge terminus towns on the East side of the Hudson, enjoy learning about their exciting pasts and vibrant presents.

This tour will help you explore the historic downtowns and nearby surrounding areas of Westchester, New York, made up of Tarrytown, Sleepy Hollow, and Irvington. Each village has its own charm.

Tarrytown is a perfect destination for a day trip from New York City. Just 25 miles from the hustle and bustle of the city, Tarrytown is a place where you can step back and experience "Main Street" America.

With its rich history of art, culture, and culinary delights, Tarrytown has attracted a long and impressive list of prominent residents over the years, including Washington Irving, Jay Gould, and Kathryn Davis.

The village of Sleepy Hollow provides a picturesque escape from the hustle and bustle of modern-day life. Visiting Sleepy Hollow makes you feel like you've stepped back in time to a simpler era.

The village is most famous for its role in Washington Irving's iconic story: The Legend of Sleepy Hollow. Although the famous story is set here, this village used to be known as North Tarrytown. In 1996 residents voted to change the name of their town to honor the community's cultural history.

Today Sleepy Hollow attracts many tourists, especially during October when local businesses and townspeople transform the village into a Halloween paradise, complete with hundreds of intricately carved jack o'lanterns, elaborate decorations, and impressive light displays.

No matter what time of year you're visiting, you'll find plenty to do here. We hope you enjoy this walking tour of Sleepy Hollow. Take your time to wander and enjoy the sites, and don't forget to be alert for the sounds of hoofbeats of the Headless Horseman because you just never know when he might show up!

As you explore the Village of Irvington, you will soon discover why it is such a great place to live, work, play, eat fast or dine elegantly. You'll also find you can easily visit with the friendly residents and business owners who will chat with you if you look lost or curious. It's such a special place that Irvington's Historic Main Street District has earned the distinguished honor of being listed on both the National and New York State Registers of Historic Places.

It has also been tagged "Hipsturbia" by the New York Times to reference the trendy residents and visitors who enjoy Irvington's charms.

We hope you enjoy this walking tour of Tarrytown, Sleepy Hollow, and Irvington. Take your time to wander and enjoy the sites, and don't forget to chat with some of the friendly locals when you stop for a bite to eat or gaze at the river views.

Tour Sponsors


This tour is presented by Historic Hudson River Towns (HHRT) with funding from New York State.

Find More Tours Near You


If you are interested in more audio tours in the region, check out the walking and biking tour of Edward Hopper’s Nyack, Walk or Bike the Gov. Mario M. Cuomo Bridge, and the driving tour of all 16 Historic Hudson River Towns.

To find more tours wherever your travels may take you visit TravelStorys.com. Every place has a story.