Legends of Sleepy Hollow

A Halloween Heritage Tour

3 Days  |  October

Starting At $Custom
Dive deep into the "Legend of Sleepy Hollow" with blazing pumpkins, gothic mansions, creepy cemeteries, and of course, the Headless Horseman. This two night tour also features a visit to Sunnyside, Washington Irving’s home, a graveyard tour where famous residents will speak from the grave, and keeping with the Halloween spirit a Dracula’s Revenge Lunch at the Rhinecliff Hotel.

Legends of Sleepy Hollow

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  • Tour of Washington Irving’s Sunnyside
  • Sleepy Hollow Cemetery Tour
  • Retelling of the “Legend of Sleepy Hollow”
  • The Great Jack O’Lantern Blaze
  • Guided Sleepy Hollow Tour
  • Costumed Guided Tour of the Clermont Mansion
  • Dracula’s Revenge Lunch at Rhinecliff Hotel
  • Free Time in Rhinebeck
  • Historic St. James Cemetery Tour
  • Two Nights First Class Lodging
  • Two Hotel Breakfasts
  • Two Dinners
  • All Taxes & Tips on these services
  • Luggage Handling
  • One Free with Every 16 Paid

Tour Options


Per Person Prices 

. . . Custom Pricing, please contact us for a quote

. . . . . . Tickets for the Great Jack O’Lantern Blaze and the Retelling of the “Legend of Sleepy Hollow”,
. . . . . . must be purchased by Aug 15 and are non-refundable.*

If you need motorcoach transportation, check out our travel affiliate Buster.com for the best prices.


Day 1 – Arrive in Sleepy Hollow this afternoon. First stop is a tour of Washington Irving’s Sunnyside, a restored home filled with the author’s possessions including his writing desk and books. A guide will tell you about Washington Irving’s storied past and how he came to be America’s first internationally famous author, best remembered now for The Legend of Sleepy Hollow and other short stories. His characters, from Brom Bones and Ichabod Crane to the mysterious Headless Horseman and the comic Rip Van Winkle, are icons in American culture.

Next, tour the Sleepy Hollow Cemetery, the spot identified in The Legend of Sleepy Hollow as the resting place of the headless horseman.  Washington Irving is laid to rest in the southern end of the cemetery in a plot overlooking the old church and its burying ground. Other famous individuals buried in Sleepy Hollow Cemetery include Andrew Carnegie, Walter Chrysler, William Rockefeller, and Elizabeth Arden.

Then check into your local hotel for a two night stay. Dinner is included tonight at Bistro Z at the Doubletree Hotel.

After dinner, you head to the Old Dutch Church for a retelling of the “Legend of Sleepy Hollow.” Master storyteller Jonathan Kruk offers a dramatic performance of Washington Irving’s classic tale, The Legend of Sleepy Hollow. Featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel.

This evening, you will head to the Van Cortlandt Manor for the Great Jack O’Lantern Blaze. This event features more than 4,000 individually hand-carved, illuminated Jack O’Lanterns.  Enhanced by professional lighting and steeped in spooky music and sound effects, this must-see event is a delight for all the senses!

Day 2 – This morning after breakfast, you will meet your local guide for a sightseeing tour of Sleepy Hollow Country.

Start with a visit to the Clermont Historic Site. Robert R. Livingston, Jr. was Clermont’s most notable resident. His accomplishments include: drafting the Declaration of Independence, serving as first U.S. Minister of Foreign Affairs, administering the oath of office to George Washington, negotiating the Louisiana Purchase and developing steamboat technology with Robert Fulton. You will tour the mansion with a historically costumed guide from Livingston’s past.

Next, you will enjoy Dracula’s Revenge Lunch at the Rhinecliff Hotel. Lunch is made with lots a garlic “to ward off the evil spirits”…but not so much garlic to be overwhelming.  After lunch, you will have free time in Rhinebeck and the unique specialty shoppes.

Then this afternoon, you will tour the Historic Graveyard at the St. James Cemetery in Hyde Park. Tour this historic 200-year old church graveyard, with re-enactors in period costume portraying famous “residents” who will speak from the grave.

Dinner is included tonight at a local restaurant.

Day 3 – After breakfast, depart for home.

Center map