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Author John Cheever is shown in 1958.

Literary Travel: Evoking John Cheever in Westchester and the Hudson River Valley

March 25, 2009
by Sarah Amandolare
The death of writer John Updike has led some to recall John Cheever, another prolific American author. The suburbs of New York City, particularly Westchester County, are the settings for Cheever’s short stories. Although the Westchester of Cheever has faded some, the small towns strung along the Hudson River still carry a literary allure.

Cheever and Updike

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According to The New York Times, Updike described Cheever as writing “with the quill from the wing of an angel.” Cheever, however, harbored a hidden competitiveness with his more commercially successful counterpart, which was ultimately revealed in his journals. Cheever’s 1978 collection of short stories was a best seller, which is rare for a book of short stories, and “went on to win both the National Book Critics Circle Award and the Pulitzer Prize.”

Cheever Country in the Hudson River Valley

Cheever lived in Ossining, a historic village in Westchester County filled with old homes, tree-lined walking paths and views of the Hudson River. According to Chris Epting, who discussed his childhood friendship with Cheever in an article for Literary Traveler, “wherever you are in the village, know that he was probably right nearby at some point.” Cheever lived with his family in a home near Teatown Lake, where he used to spend time with Epting.

But the so-called “Cheever country” is not what it used to be, according to Malcolm Jones of Newsweek, who lives “not five miles from Ossining.” In particular, the commuters hopping daily trains into Manhattan have changed drastically over the past two decades, becoming less homogenous and more of a “plural, motley community that subscribes to no single orthodox code of belief or behavior,” writes Jones. Cheever’s most story-worthy subject matter, “the anxieties that gave his stories a lot of their pop,” were left behind a generation ago, according to Jones.

Furthermore, Ossining has not fully embraced Cheever, according to Updike, who, before his death, reviewed Blake Bailey’s lengthy biography “Cheever: A Life,” for an early March 2009 issue of The New Yorker. Updike wrote, “In Ossining, New York, where he lived for decades as the town’s most prominent citizen, a move to name a short street after him was turned down at a town meeting, and only the main reading room of the public library honors his memory.”

Hudson Valley by Train, Car and Boat

The best way to experience the Hudson Valley is to drive or take a train ride along the river, making various sightseeing stops along the way. From New York City, board the Metro-North Hudson Line, which makes stops in Ossining and many other quaint Hudson River towns, including Tarrytown and Cold Spring. Cold Spring features great kayaking, hiking at Breakneck Ridge, antiques shopping and comfortably classy dining.

On adventure travel site GORP, Claire Pamplin has advice for driving in the Hudson Valley. “Visibility is best in winter, when the trees are bare,” she explains. “However, when the trees leaf out and wildflowers bloom in spring, you will experience the valley’s most uplifting time.” Pamplin also discusses driving “along the west side of the river in New Jersey,” and shares favorite attractions further north along the river in upstate New York, including Franklin D. Roosevelt’s home and the sprawling grounds of the Vanderbilt Mansion in Hyde Park.

Boating enthusiasts also flock to the Hudson Valley. The New York State Department of Environmental Conservation lists Hudson River estuary public fishing and boating access maps, including Stony Point, which has boat launches in Westchester and Rockland Counties.

Historic Hudson Valley

The Hudson River Valley has Dutch settler roots, according to Historic Hudson River Towns of Westchester. Enticed by “Henry Hudson's explorations up the Hudson River,” settlers arrived and found work in the 1800s and early 1900s on the canals and railroads that linked the Hudson Valley with the rest of the state. Among the area’s famous residents were the Rockefellers and Washington Irving, author of “The Legend of Sleepy Hollow.”

To experience a guided tour of the Hudson River Valley National Heritage Area, take a train ride with New York By Rail and I Love New York; the team’s “Windows on History: Exploring the Hudson River Valley National Heritage Area” features “narratives, historic depictions, and photos taken from the perspective of passengers on the train” to explain the landscape passing by outside the train windows.
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