Throughout the 18th century, Tarrytown remained a key link in New York City’s supply chain — farming, milling and shipping grain downstream to the growing metropolis.  Sloops carried wheat, barley and corn to the city and returned carrying goods for sale to farmers and their households. Tarrytown seemed destined to become an important stop for travelers. Beginning with the opening of a 154-mile post road connecting New York City to Albany in 1703, stage coaches would regularly “refuel” — with fresh horsepower and refreshments — in the village. The trip took roughly three days, with a stagecoach fare costing $8 — the equivalent of $515 in today’s dollars.

Although Irving made a living as a writer — with Europe acknowledging him as America’s first world-class literary talent — he was engaged during his lifetime in numerous other pursuits as well. He lived in Europe for 17 years, residing in London; Paris; Dresden; and Madrid. While he was abroad, he tried unsuccessfully to repair the financial damage his family’s trading company suffered during the War of 1812. Later, he worked for the American Minister to Spain and for the American delegation in London. In 1835, three years after his return to New York, destiny guided him once again to Tarrytown, where he purchased a ramshackle colonial cottage on 10 acres along the shore of the Hudson for $1,800 (more than $51,000 in today’s dollars). He called his home Sunnyside. In all the years Irving had spent travelling, he had never had a home of his own; now he did, and he worked tirelessly to transform it from a two-room stone farmhouse built in the 1690s to an “elegant little snuggery,” as he called it, surrounded by a park-like landscape of his own design. 

Though he wrote everything from travel pieces to biographies, Washington Irving’s best-known and best-loved tales remain “Rip Van Winkle” and “The Legend of Sleepy Hollow.” His influence also remains alive to a remarkable degree in everyday language and culture. He is credited, for instance, as first to use the term “Gotham” to describe New York City. He also dreamed up the vaguely Dutch-sounding word “knickerbocker” to reference someone or something from Manhattan (its shortened version of “Knicks” is the colloquial name of New York’s professional basketball team). Irving’s popular history of Christopher Columbus, written in 1828, is the source of the long-lasting — but mistaken — notion that medieval Europeans believed the Earth was flat.

Commerce and industry took over in the 20th century, tying the village to its neighbor, and it was renamed North Tarrytown in 1883. But before that, the village was called Beekmantown, and not Sleepy Hollow. In the 1980s, the idea of officially changing the name to Sleepy Hollow arose from a desire to connect with its past. But it wasn’t until 1996, the same year the General Motors plant closed, that the village voted to rebrand itself under the name of Sleepy Hollow.

In the last half of the 19th century, Washington Irving’s legends gave way to real-life titans — Jay Gould, Madam C.J. Walker, and John D. Rockefeller — who used oil, steel, railroads, and banking to transform America. They made vast amounts of money, which they spent lavishly on elaborate showpiece estates up and down the river, from the hills above Troy to the Hudson shore in the Bronx. Mark Twain and his friend Charles Dudley Warner co-authored a novel in 1873 called “The Gilded Age” to describe the greed, waste and excess of the day. The title struck a nerve and has remained in the American lexicon, along with another new term, “millionaire.” In fact, there were so many grand estates in the Tarrytown area that it came to be known as a “millionaires’ colony.”

Many of the stately homes built along the Hudson were architectural masterpieces, made of locally quarried stone and built by the Irish, Italian, German and other immigrants who flocked to the United States during the 19th century. In addition to providing employment opportunities during their construction, once they were completed these great homes hired residents from the community to serve as members of the household staff. Lyndhurst, Kykuit (pronounced Ky-kit) and many other Hudson River homes and historic sites still stand today and are open to the public.

One of the grandest of the Hudson River estates, the massive Gothic Revival mansion called Lyndhurst, dates to 1838. It served first as home to William Paulding, a former mayor of New York City, followed by George Merritt, a successful merchant who bought the place in 1864 and doubled its size. In 1880, the notorious railroad magnate Jay Gould — some called him a “Robber Baron” — purchased the property. The great oil tycoon John D. Rockefeller, founder of the Standard Oil Company and the richest man of his time, built a 40-room country estate for himself in 1893 on a high point of land just north of Lyndhurst in the village of Sleepy Hollow. The 2,300-acre Rockefeller estate is called Kykuit, which in Dutch means “lookout.” 

The opening of the bridge in 1955, and its connecting roadway, the Cross Westchester Expressway (I-287) just five years later, linked Rockland and Westchester with Connecticut. The openings paved the way for a new corporate mecca alongside Westchester Avenue, parallel to I-287, which is known today as the Platinum Mile. New jobs stimulated population growth and housing demand on both sides of the river for workers benefiting from new access to the job market via the Tappan Zee Bridge.

In order to build this span over the railroad tracks without interrupting service, engineers cantilevered more than 2,000 tons of structural steel using a specially-designed track system.