At 105 miles, the Taconic State Parkway is the longest in the Empire State’s sprawling system of landscaped limited-access roads. Starting at the 300-foot-tall Kensico Dam in Valhalla and ending 30 miles outside Albany, the Taconic winds through four Hudson Valley counties, from the suburbs of Westchester through the craggy woodlands of Putnam and Dutchess to the rolling farmland of Columbia. Though it would take nearly 40 years to build, initial planning for this marvel of 20th century landscape and road design began a century ago, in 1925, pushed by a pesky local landowner. His name was Franklin Delano Roosevelt.
During his childhood in Hyde Park, Roosevelt had spent many happy days traversing the woods and backroads of his native Dutchess County. Upon entering politics, Roosevelt set his mind to conserving the region’s most charming places and views from development. Stricken with polio in 1921, Roosevelt returned to public office four years later when Governor Al Smith appointed him to lead the Taconic State Park Commission, charged with building a park system in the eastern Hudson Valley. Roosevelt realized that in order for people to get to those parks, a new road would be needed to guide them there.
Roosevelt wanted the road to be as lovely as the parks. As he had chauffeurs drive him around the region, he made sketches of picnic tables and thought about which types of rock should be used to face the bridges and rest stops along the way. He even hoped to extend the parkway to Canada.

In 1931, Roosevelt, having succeeded Smith as governor, presided over a ceremony at Shrub Oak in Westchester to mark the beginning of construction. But it was only in 1949, four years after Roosevelt’s death, that his successor, Thomas Dewey, also a Dutchess resident, celebrated the opening of the first segment, 21 miles long.
Tasked with taming a forbidding terrain—taghkanic is thought to be the Mohican word for “wooded mountains”—landscape architect Gilmore Clarke, who also designed the Central Park Zoo and the Unisphere from the 1964 World’s Fair, collaborated with engineers and construction crews to create banked curves that would help minimize blind spots and highlight the magnificent views. Carefully chosen vegetation preserved the natural landscape, integrating the parkway with its gorgeous surroundings.
The Taconic winds through four Hudson Valley counties, from the suburbs of Westchester to the farms of Columbia.
By 1963, when the last stretch of road was completed, the Taconic was already a throwback—the federal Interstate Highway System of the 1950s fostered a more unsightly, utilitarian style. These days, the parkway is used less for the rambling recreational drives envisioned by Roosevelt than by commuters traveling at far higher speeds than expected by the parkway’s creators. Although improvements have made a few of the areas safer, the Taconic maintains its reputation as a treacherous roadway.
Yet also an especially scenic one. A century after its conception, the Taconic remains, as Ian Fleming wrote in Diamonds Are Forever (1956), in which his hero James Bond takes it on a road trip to Saratoga Springs, “one of the most beautifully landscaped highways in the world.”
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