Historic Hudson and Sleepy Hollow

Who is ready for Sleepy Hollow cemetery exploring, a lantern tour, and a visit to Sleepy Hollow Lighthouse? This spooky tour is for you! Witness an army of glowing Jack O'Lanterns, learn about history at The Historical Society and Museum, visit old castles & mansions, and so much more!

5 Days /4 Nights

Group size

Estimated Tour Pricing Inclusions: 4 nights’ accommodation; 3 breakfasts; 3 lunches; 2 dinners; admissions, entrance, and guide fees as stated in the itinerary, including taxes, and gratuity. Except gratuity for guide fees is not included on adult tours unless otherwise requested.
  • Philipsburg Manor
  • Sleepy Hollow Cemetery
  • Sleepy Hollow Lighthouse
  • Rockefeller Estate
  • The Great Jack O’Lantern Blaze
  • The Historical Society and Museum
  • West Point Military Academy
  • Vanderbilt Mansion
  • The Culinary Institute of American-Hyde Park
  • Home of Franklin D. Roosevelt
  • Historic Huguenot St.
  • Perkins Memorial Dr.

Sample Itinerary:
Day 1 - Philipsburg Manor & Sleepy Hollow Cemetery
  • Depart for New York, arrive, and enjoy lunch included. Explore this local eatery with farm-to-fork New American fare & biodynamic wine, plus a gourmet shop.
  • Depart for Philipsburg Manor for a tour. Experience 'The Unsilent Picture'. Across busy Broadway from the Old Dutch Church is Philipsburg Manor Restoration, an interpretive historic site that reflects life during the 17th century.
  • Stop at the Sleepy Hollow Lighthouse.
  • Enjoy dinner included this evening at a local favorite.
  • Arrive to Sleepy Hollow Cemetery and depart on a Lantern Tour. Soak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including William Rockefeller, Andrew Carnegie, John Dustin Archbold and others resting in peace in the north end.
  • Check-in to your hotel for the evening. (Meals: L, D)
Day 2 - Rockefeller Estate & The Great Jack O’Lantern Blaze
  • Enjoy breakfast at the hotel before checking out.
  • Depart for the Lyndhurst Welcome Center, a majestic estate on the banks of the magnificent Hudson River where every visitor can experience firsthand an American icon of architecture and landscape. Whether you are a first-time visitor or returning guest there is always something new to discover.
  • Visit Kykuit – The Rockefeller Estate. A majestic paradise with sweeping river views. Kykuit was home to four generations of the Rockefeller family, beginning with the philanthropist John D. Rockefeller, founder of Standard Oil. His business acumen made him, in his day, the richest man in America. Now a historic site of the National Trust for Historic Preservation, this extraordinary landmark has been continuously and meticulously maintained for more than 100 years.
  • Enjoy free time and lunch on own in downtown Tarrytown. Later, arrive at The Historical Society and Museum that collects, preserves, and celebrates the history of Tarrytown and Sleepy Hollow. The Historical Society has been the keeper of the collective memories of the villages of Sleepy Hollow and Tarrytown since 1889.
  • Arrive to The Great Jack O’Lantern Blaze where you witness an army of more than 7,000 glowing, intricately carved pumpkins shining along the riverside near Van Cortlandt Manor. Ogling pretty gourds isn’t the only draw. There are also "stargazing" opportunities inside the Pumpkin Planetarium, flying ghosts and a special appearance by Sleepy Hollow’s Headless Horseman.
  • Enjoy dinner included this evening at a local favorite Italian Restaurant this evening. Return to the hotel. (Meals: B, D)
Day 3 - West Point, Vanderbilt Mansion, & The Culinary Institute
  • Enjoy a leisurely breakfast at the hotel this morning before checking out.
  • Depart for West Point Military Academy and check in at the Visitors Center. Take a Guided Tour of the academy in a combined bus and walking tour which tells the story of West Point, its role in the Revolution, its famous history along with stories about graduates who shaped our nation The tour will bring the Long Gray Line to the present as you learn of the cadet experience and West Point’s continuing role in training the leaders of tomorrow. This tour goes around the post with stops at the Main Cadet Chapel, West Point Cemetery, Old Cadet Chapel, and Trophy Point overlooking the Hudson River and the Plain.
  • Enjoy lunch included overlooking the Hudson River.
  • After lunch, arrive at the Vanderbilt Mansion and check-in for your tour at the Pavilion Visitor Center. Historically known as Hyde Park, Vanderbilt Mansion National Historic Site is one of the region's oldest Hudson River Estates. For nearly two centuries, this place has been home to socially prominent New Yorkers. A superb example of its type, Hyde Park represents the domestic ideal of the elite class in the late nineteenth-century America. It provides a glimpse of estate life, the social stratification of the period, and the world of the American millionaire during the era historians refer to as the Gilded Age.
  • Next, arrive at the Culinary Institute of America-Hyde Park and enjoy free time to explore the breathtaking campus.
  • Enjoy a private four course dinner included at one of the Culinary Institute of America’s famous restaurants. Check-in to your local hotel for the evening.  (Meals: B, L, D)

Day 4 - Walkway Over The Hudson River & FDR Home
  • Enjoy breakfast at the hotel.
  • Stroll over the Hudson River on the Walkway Over the Hudson Guided Tour. The Walkway over the Hudson is a linear walkway spanning the Hudson River. At 212 feet tall and 1.28 miles long, it is the longest, elevated pedestrian bridge in the world. Take in breathtaking, unobstructed 360-degree views of the Hudson River and the surrounding scenic valley as your guide tells stories about the past, present, and future of the Walkway.
  • Visit the FDR Presidential Library. The Franklin D. Roosevelt Presidential Library and Museum is America's first presidential library and the only one used by a sitting president. It was conceived and built under President Roosevelt's direction and opened to the public in 1941.
  • Enjoy lunch on own while visiting.
  • Take a guided tour of the Home of Franklin D. Roosevelt. The Home of Franklin D. Roosevelt National Historic Site contains "Springwood", the lifelong home of America's only 4-term President.
  • Depart for the Old Rhinebeck Aerodrome for a WWI Air Show, Fall Festival, and Pumpkin Bombing event! The Old Rhinebeck Aerodrome is a true “living” museum of antique aviation located in the historic town of Rhinebeck, New York. The museum presents one of the largest collections of early airplanes in the world, many of which regularly take to the air for thrilling demonstrations during weekend airshows. The Aerodrome features airplanes, automobiles, motorcycles, early engines, and memorabilia from 1900-1935. In addition to the airshows, there are four museum buildings displaying aircraft from the Pioneer Era, World War I, and the Lindbergh/Barnstorming era. Enjoy farewell dinner included. 
  • Depart and return to your hotel for the evening. (Meals: B, D)
Day 5 - Historic Huguenot St. & Perkins Memorial Dr.
  • Prior to checking out, enjoy a leisurely breakfast in the main dining hall with panoramic views of the Catskill Mountains. Take your pick and delight in several Chef Action Stations.
  • Visit Historic Huguenot Street. Take a guided tour featuring the Replica Esopus Munsee Wigwam, the 1717 Reconstructed French Church, and the Abraham House.
  • Arrive at Brotherhood, America's Oldest Winery. Experience the enigmatic atmosphere of Brotherhood Winery by taking a leisurely stroll through their vast network of underground cellars. Excavated by hand in the late 19th Century, the dimly lit cellars house over 200 oak barrels and feature a crested vault containing some of the oldest vintages in America.
  • Enjoy a farewell lunch included. The restaurant offers a casual, rustic atmosphere and an eclectic menu of modern takes on American classic dishes that burst with flavor.
  • Drive to the top of Bear Mountain via the Perkins Memorial Drive for 360-degree views of the Hudson River Valley. Depart for home. (Meals: B, L)

Base rate does not include motor coach transportation, airfare, airport transfers, driver gratuity, guide gratuity, (student groups exempt) or any upgrades or add-ons unlisted from itinerary as stated. Pricing may vary based on day of arrival or other conditions. Personalized itineraries with custom pricing and/or additional transportation can be created and added based on client needs and upon client’s request. MARS will customize quotes or personalize itineraries for FREE.

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