Sleepy Hollow-een Adventure - 2022

Fully Guided tour with Bill Ball, host of 2 Travel Series: Journeys in India and Journeys in Africa, seen Nationally on Public Television will guide your tour from start to finish. He has guided tours on all 7 continents and over 100 countries. Join him on this new offering from Passport Travel Tours.

5 Day Tour: October 6-10, 2022


Base Tour Pricing

Double Occupancy, Per Person
  • Base Pricing is always calculated for double occupancy.
Solo Traveler
  • $480 supplemental for Solo Travelers.

Tour Highlights


Historic Landmarks


Places to See
Before You Die



National Parks

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Tour Includes

  • Roundtrip airfare from Chicago
  • First Class Hotel Accommodations
  • Daily Breakfast
  • 3 Dinners
  • Deluxe Motorcoach Transportation
  • Admissions to all listed Attractions
  • Roundtrip airport transfers in the Chicagoland area
  • Guided by Bill Ball
  • Baggage Handling
  • All Gratuities

Tour Itinerary

Day One We fly to New York state to begin our one hotel tour into the other world.  We begin where it seems most fitting at the mansion of the master of Sleepy Hollow himself, Washington Irving.  He once described his home as “all made up of gable ends and as full of angles as an old cocked hat.”  Our final stop of the day (as long as it’s not your final stop forever…)is not unexpected but the center of the night life of the area—Sleepy Hollow Cemetery where Washington Irving and Andrew Carnegie are buried.

Day Two  We step back in history today with a visit to the famed West Point Academy including the campus and museum that boasts the likes of Ulysses S. Grant, Robert E. Lee and Dwight D. Eisenhower among its illustrious graduates.  In keeping with our military and history theme, we will dive into the Revolutionary War and visit one of the places the US troops wintered, no not Valley Forge—Major General Knox Headquarters.  See the buildings and fields where America was born.  We have a special treat for this evening—a dramatic reading of the “Legend of Sleepy Hollow” by master storyteller Jonathan Kruk.  Flavored with live spooky organ music, this yearly sold out event will captivate all ages.

Day Three  We begin the day getting back to nature at the Audubon Center.  We’ll take advantage of the fall migration season to see a great range of birds in a beautiful marshland.  This afternoon we head to Hyde Park to follow the life of FDR touring his family home and Presidential Library and visiting his grave (another place of the dead—what is this Halloween?) Then, not to forget Eleanor, we’ll visit her private home Val-Kill and learn how she helped change the world.  This evening we visit the most spectacular Halloween display in the world—The Great Jack O’Lantern Blaze.  Over 4000 hand carved illuminated jack o’lanterns form scenes like the Egyptian pyramids, super-sized dinosaurs and pirates.  This is a sold out event but not for you!

Day Four  Time to take in the fullness of the fall colors by venturing up into the Catskills.  Our first stop will be the Thomas Cob National Historic Site.  He was the founder of the Hudson River School of Art and his magnificent home and studio reflects his love of the landscapes we see today.  Just an amazing bridge away is another great home and scenic wonder—Olava—home of fellow artist Fredric Church.  We’ll walk his beautiful garden and approach  the front entrance as guests before we proceed inside.  From this property, we can see the Hudson River Valley  below us—breathtaking.  Our last stop will be the amazing Kaaterskill Falls.  You can either access it by the viewing platform or join Bill as he hikes less than 1 1/2 miles round trip.  This is a sight worthy  of this magnificent 260 foot high falls.  All in all, it’s a day to enjoy the colorful landscape and quaint villages that make up the Catskills.

Day Five  Before Bill will let you go home he has one more surprise for you.  We hope you won’t lose your head over it.  We then head home with warm spooky thoughts of Halloween and the eye candy of the fall colors.  What a combination!