Experience the legends and autumn beauty of New York’s Hudson Valley as you step into the story of Sleepy Hollow. Explore the village where the tale of the Headless Horseman began, cruise along the Hudson River surrounded by brilliant fall color, and enjoy a dramatic retelling of the famous legend by a master storyteller. Along the way, you’ll visit historic West Point, savor a tasting at America’s oldest winery, stroll charming river towns, and experience the glowing magic of the Jack O’Lantern Blaze. As night falls, you may even catch a glimpse of the Headless Horseman himself!
- Explore the Hudson Valley surrounded by brilliant fall foliage, historic lighthouses, and scenic river views
- Tour the US Military Academy at West Point (Note: REAL I.D. or valid U.S. Passport required for visit to the U.S. Military Academy)
- Experience the glowing displays of the spectacular Jack O’Lantern Blaze
- Enjoy a live retelling of The Legend of Sleepy Hollow at the home of author Washington Irving
DAY 1: WELCOME TO NEW YORK!
This evening, arrive in New York and enjoy a welcome dinner with your fellow travelers. D
DAY 2: HUDSON RIVER CRUISE, KINGSTON, FDR HOME
This morning, travel to historic Kingston and board the Rip Van Winkle II for a scenic cruise along the Hudson River. Notable sights include lighthouses, waterfront mansions, and stunning fall foliage. Enjoy free time for lunch and shopping in Kingston before visiting the home of Franklin D. Roosevelt in Hyde Park. Tonight, check into your hotel and enjoy a group dinner with your fellow travelers. B, D
DAY 3: WEST POINT, BROTHERHOOD WINERY, LEGEND RETELLING
This morning, travel to West Point for a guided tour of the U.S. Military Academy, beautifully set above the Hudson River. Continue to Brotherhood Winery, the oldest operating winery in the United States, where you’ll tour the historic cellars before enjoying lunch and a tasting. Return to Sleepy Hollow this afternoon for free time and dinner on your own. Tonight, gather under the stars at the home of Washington Irving as master storyteller Jonathan Kruk brings The Legend of Sleepy Hollow to life in a dramatic live performance. B, L
DAY 4: SLEEPY HOLLOW
Spend today immersing yourself in the history of Sleepy Hollow by exploring some of the town’s sites with a local guide. This afternoon, take a tour of Sleepy Hollow Cemetery, the final resting place of notable figures and the setting that inspired Washington Irving’s famous tale. Tonight, gather with your fellow travelers for a memorable farewell dinner at the Old ’76 House, a tavern which played a role in the American Revolution. Finish off the night with a visit to the spectacular Jack O’Lantern Blaze, where thousands of intricately carved pumpkins illuminate elaborate, glowing displays. B, D
DAY 5: ALPACA FARM, RETURN HOME
After breakfast, journey into the rolling hills of the Hudson Valley for a visit to Faraway Farm Alpacas. Enjoy an up-close experience with the gentle animals while learning about fiber production. This afternoon, return home with happy Halloween memories. B
ACCOMMODATIONS
Nights 1-4: Westchester Marriott, Tarrytown, NY
Departure Cities:
- St. Louis
- Kansas City
Depart: October 9, 2027
Return: October 13, 2027
Price per person:
- DB $2,999
- TP/QD $2,899
- SG $3,599
Price per person includes roundtrip airfare from STL, MCI. Please call for other gateway cities.
Other General Information
Tour Communications: You will receive three key communications leading up to your tour:
- Get Ready: Your email confirmation and initial tour information, sent after you register.
- Get Set: An email with additional tour details, sent approximately two months before departure.
- Go: Your final trip documents, mailed via USPS approximately three to four weeks before departure. This packet will include your daily itinerary, luggage tags, and final departure information.
Travel Protection: Travel Protection is optional but highly recommended and may be purchased until the day before departure. Sunrise Tours offers plans through battleface. Additional information will be included with your Get Ready email and can also be found HERE.
Inclusions: Unless otherwise noted, your Sunrise Tour includes:
- A professional Sunrise Tour Director
- Meals as indicated in the itinerary
- Local step-on guides, including gratuities
- International tour guide gratuities when specified for the individual tour
- Deluxe motorcoach transportation with an onboard restroom
- Admission to activities and events as indicated
- Airfare from designated airports
- Transportation to and from designated airports from our convenient local pickup points*
- Luggage handling at hotels when available
Gratuities: We believe tipping is a personal and discretionary interaction between our guests and staff. A typical gratuity for your Sunrise Tour Director and motorcoach driver is $6 to $10 per person, per day of the tour. Sunrise Shuttle drivers also appreciate gratuities for excellent service, with a suggested amount of $5 per person. Our staff will not solicit gratuities or distribute gratuity envelopes.
Refreshments: We are happy to provide refreshments on most motorcoach travel days. We also recommend bringing a refillable water bottle to help you stay hydrated throughout your tour.
Pickup Points: If fewer than four travelers request a particular pickup point, we may ask those guests to select another available pickup location. Travelers are also welcome to join a tour from a city that is not listed as a departure point. Please contact our friendly reservations team to discuss available arrangements. For departure cities not listed, airfare is typically $100 more than the published fare for domestic tours and $200 more for international tours.
TSA PreCheck and Airline Rewards Numbers: TSA PreCheck, Known Traveler Numbers, and airline rewards numbers must be provided to our reservations team at least 60 days before departure. Numbers received after this deadline may not be applied to your reservation.
Airline Seating: Preferred seating may not be available with group airfare. In some cases, seats are not assigned until travelers arrive at the airport. Your tour fare includes an economy-class seat but does not include advance seat selection. Seat upgrades may be available for an additional cost.
Motorcoach Capacity and Seating: To provide one of the most comfortable motorcoach experiences in the industry, Sunrise Tours generally limits motorcoaches to 80% capacity. This allows for a maximum of 44 passengers on a motorcoach designed to accommodate 55. Sunrise Tours reserves the right to amend this practice. Your Tour Director will rotate motorcoach seating each day of the tour. Payment of a single-occupancy fare does not guarantee two motorcoach seats, and you may be seated beside another friendly Sunrise Tours guest.
Terms and Conditions
Please refer to our policies HERE for more information on our terms and conditions.
