Sleepy Hollow Weekday Whirlwind
Date & Time
Mon, 05 Oct, 2026 at 05:00 pm to Wed, 07 Oct, 2026 at 01:00 pm
UTC-04:00Location
Knoxville, Tennessee | Knoxville, TN
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Details
Join us for a weekday whirlwind adventure to Sleepy Hollow (Tarrytown), New York, October 5-7!Your whirlwind adventure begins Monday evening, October 5th, as we travel overnight in the comfort of a deluxe motorcoach, allowing you to wake up in the heart of New York's beautiful Hudson Valley. After a morning stop to freshen up, you'll arrive in historic Sleepy Hollow, Tuesday October 6th, where you'll have the entire day to experience this iconic destination at your own pace.
Stroll through the charming streets lined with colorful autumn leaves, browse unique local shops and cafés, and immerse yourself in the village made famous by Washington Irving's The Legend of Sleepy Hollow. History enthusiasts will enjoy visiting landmarks such as Sleepy Hollow Cemetery, the final resting place of Washington Irving, as well as historic churches and centuries-old architecture that inspired one of America's most beloved ghost stories.
October is the perfect time to visit because the entire community embraces the Halloween season with festive decorations, special events, haunted attractions, seasonal food, and an atmosphere unlike anywhere else in the country. Around every corner you'll discover pumpkins, fall colors, and the unmistakable charm that has made Sleepy Hollow a bucket-list destination.
As evening falls, your adventure continues with one of the Northeast's premier Halloween attractions—the Great Jack O'Lantern Blaze at Van Cortlandt Manor. Wander through an incredible display of more than 7,000 hand-carved illuminated pumpkins, featuring breathtaking arches, sculptures, animated displays, and larger-than-life works of art. Frequently recognized as one of the top Halloween experiences in the United States, the Blaze is a spectacular event that perfectly captures the magic of the season.
Following the Blaze, you'll begin the overnight journey home, arriving back in Tennessee Wednesday afternoon with unforgettable memories, incredible photos, and a newfound appreciation for one of America's most legendary fall destinations.
Trip Highlights
🎃 Explore historic Sleepy Hollow during peak fall foliage
🍁 Experience the charm of New York's scenic Hudson Valley in October
📚 Walk in the footsteps of Washington Irving and the Legend of the Headless Horseman
✨ Admission included to the world-famous Great Jack O'Lantern Blaze
🚌Pickups in Farragut, Knoxville, Morristown, & Bristol
Whether you're a Halloween enthusiast, history buff, photographer, or simply someone who loves the beauty of autumn, this Monday–Wednesday Whirlwind Adventure offers the perfect opportunity to experience one of America's most iconic fall destinations.
Reserve your spot on thisnew adventure by calling our office Monday-Friday at 865-523-2796.
Cost is $280 per person
$50 deposit due at time of registration with remaining balance due by Friday, September 4th!
Event Location
Knoxville, Tennessee, United States
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Event Host
Travel by Olympus
