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Sailing Through History

  • nigeledelshain
  • Dec 10, 2025
  • 4 min read

HERE IN SOUTH FLORIDA, we are well-acquainted with the yearly influx of snowbirds, those winter-weary residents from the Northeast, Canada, and other cold environs who journey here to enjoy the sunshine and sand. For South Floridians who seek a change of seasons, however, we must journey in the other direction—which is exactly what my wife Pam and I did on a recent trip to upstate New York, where we boarded the American Cruise Lines ship American Glory for a nine-day Fall Foliage Cruise, taking us from New York City to Albany along the Hudson River.


And while the hotter than normal weather and drought affected the normal dazzling array of yellows, oranges, and reds, the cruise itself had a lot of fascinating history to offer, from Gilded Age mansions and pivotal Revolutionary War sites to the birthplace of one of America’s most iconic spooky stories and the 315-mile river itself—named for English navigator Henry Hudson who explored it in 1609.


If that sounds like your idea of a good time, sit back, imagine you are in a lounger enjoying your favorite drink on American Glory’s sundeck with us, and settle in for a leisurely, peaceful, and eye-opening ride up the mighty Hudson.


Sleepy Hollow. Our first stop is the picturesque town in which author Washington Irving set his famous 1820 story, “The Legend of Sleepy Hollow.” Here you’ll find the Old Dutch Church, where the fictional Ichabod Crane was choirmaster as well as a reconstruction of the Headless Horseman Bridge. Nearby, alongside a large oak overlooking the Hudson River Valley, is the final resting place of Irving himself. Some locals say the cemetery is haunted. We didn’t stick around to find out.


West Point. Established by Thomas Jefferson in 1802, West Point is the nation’s oldest military academy. On this crisp autumn day, cadets jogged by as we visited Trophy Point, the spot overlooking the Hudson where artillery captured from America’s wars is on display, as well as links from the massive iron chain Revolutionary War forces deployed in 1778 to thwart British efforts to gain strategic control of the river. The museum and visitor center are exceptional, and you won’t want to miss the imposing Gothic Revival Cadet Chapel, either, which houses the world’s largest pipe organ—comprised of over 23,000 pipes for those who are counting.


Kingston. In 1825, the construction of the Erie Canal linked Lake Erie, the Hudson, and the Atlantic Ocean and provided a vital synergy of commerce and industry. The Hudson River Maritime Museum here in Kingston, the one-time capital of New York, houses more than one million artifacts showcasing that history of the Hudson River. More than a museum, the center also offers schools for wooden boat building and sailing as well as tours to the Rondout Lighthouse, the last of three working lighthouses on Rondout Creek. Dating from 1837, the current structure was opened in 1915 and is only accessible by boat. When lighthouse keeper George Murdock drowned in 1856, his widow, Catherine, took over as keeper for the next 50 years. Just up the street from the museum is the Half Moon Rondout Café; don’t leave without trying their apple cider donuts.


The Catskills. During the Gilded Age, business titans such as the Vanderbilts, Rockefellers, and Jay Gould built lavish estates on the Hudson, including this longtime favorite playground for New Yorkers. American landscape painters of the famous 19th century Hudson River School, led by Thomas Cole and his student Frederic Church, sought to capture this natural beauty on canvas. In the Catskills you can visit Church’s own Olana, a majestic Persian architecture-inspired estate—it is, in fact, named after an ancient Persian house—set on 250 acres overlooking the Hudson River valley and Catskill Mountains. Later, on a drive in which fall foliage was more bountiful, we discovered the nearly mile-long Rip Van Winkle Bridge, which connects Hudson and Catskill, includes a pedestrian walkway, and, yes, is named after another Washington Irving story.


Hyde Park. Alas, a government shutdown nixed tours of the Franklin D. Roosevelt National Historic Site, birthplace of the thirty-second president, and Vanderbilt Mansion. Seeking to make lemonade from lemons, however, we visited nearby Rhinebeck, a charming colonial town spotted with numerous shops, art galleries and bookstores that is also home to The Beekman Arms & Delamater Inn, in operation since 1766. (Famous past guests include both George Washington and Alexander Hamilton.) Pro tip: Don’t pass up the cupcakes at Samuel’s Sweet Shop, co-owned by actor Paul Rudd and his wife, or the fudge at Krause’s Chocolates, which Pam insists is to die for.


Troy. Our cruise concludes In Troy, nicknamed “Collar City” during the Gilded Age because it produced more than 90% of men’s detachment starched collars. It is also the birthplace of “Uncle Sam,” the national icon modeled on Troy businessman Samuel Wilson. The area is steeped in fascinating history—if you have time, take a side trip to the Burden Iron Works Museum—and served as a stand-in for 1880s New York in the HBO series, The Gilded Age. (During filming, some streets had to be covered in dirt and A/C units removed from windows.)


It’s a fitting end to another adventure for Pam and I. Perhaps we’ll see you on the next one?


BY GERRY BARKER

 
 
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