CELEBRATE “THE LEGEND OF SLEEPY HOLLOW” BICENTENNIAL | Sleepy Hollow Book Club

The “Legend of Sleepy Hollow” by Washington Irving is celebrating its bicentennial; first published 200 years ago in Irving’s collection of 34 essays and short stories entitled “The Sketch Book of Geoffrey Crayon.”

Jump to Part 1: Get to know the Author
Jump to Part 2: The setting of Sleepy Hollow, New York
Jump to Part 3: Favorite quotes and connections

The Sleepy Hollow Book Club was thrilled to celebrate with our members all October long with special guests, giveaways, plus these 5 ways that you can participate from wherever you are!

If case you’re not familiar with “The Legend of Sleepy Hollow” it’s one of America’s first famous ghost stories. It is set in 1790 and follows schoolmaster Ichabod Crane as he begins teaching in the little Dutch village of Sleepy Hollow in the Hudson Valley of New York and finds himself haunted by the Headless Horseman. Information has kindly been provided by Char Weigel, Trustee, The Historical Society Serving Sleepy Hollow and Tarrytown

PART 1: Let’s start by getting to know the author with 5 fun facts about Washington Irving

-Irving was born in New York City on April 3, 1783. He started his professional life as a lawyer, but he was destined to be a writer. While studying for the law, he wrote funny pieces about the New York City theater scene for the Morning Chronicle under the pseudonym “Jonathan Oldstyle.” With his brother William and good friend James Kirke Paulding, he created the satirical periodical Salmagundi, writing witty, and often naughty, pieces on New York politics and culture under the name of “Launcelot Longstaff.”

-Many of our common phrases and cultural icons came from Irving. He created New York City’s nickname “Gotham.” He wrote under the pseudonym “Diedrich Knickerbocker” which eventually gave the NY Knicks their name. He popularized the phrase “the almighty dollar.” And, of course, he brought the concept of Santa Claus to America by writing about St. Nickolas who brought presents to children in a wagon and then disappeared as he rode away over the treetops.

-Irving was such a convincing writer that many people still quote his fiction as fact. In The Legend of Sleepy Hollow, he makes a convincing argument that Tarry Town was named by a group of housewives whose husbands tended to “linger about the village tavern on market days.” In fact, Tarrytown is more likely derived from “tarwe,” the Dutch word for wheat, which was one of the main crops in the area brought to the nearby Upper Mill of the Philipse family.

-Irving was proud of being named after George Washington. He often told the story of when he was a small boy and out on the streets of New York City with Lizzie, one of the women who worked in the Irving household. Lizzie saw George Washington and introduced young Washington to the President who laid his hand on the head of the six year old Irving and gave him his blessing.

-Washington Irving died November 28, 1859 and his grave is in the Sleepy Hollow Cemetery, looking out over the Old Dutch Church and surrounding Burying Ground of which he wrote. Although Irving never married or had children, he is surrounded by many family members in a large family plot. It is one of the most popular spots for tourists visiting Sleepy Hollow today.

“Little minds are tamed and subdued by misfortune; but great minds rise above them.“

-Washington Irving

SLEEPY HOLLOW BOOK CLUB | Discussion Questions (Part 1) | If you’re not a member yet, sign up to get newsletters from It’s a Charming Life.)

• Washington Irving was known as the “father of the American short story” yet so few seem to know his impact on New York and the United States’ holidays. Did you already know who was the author of “The Legend of Sleepy Hollow” and “Rip Van Winkle”?
• What is your personal favorite film adaptation of the Legend and have you read the short story before?
• Why do you think it is still widely read today (especially around Halloween)?

PART 2: The Setting of Sleepy Hollow and Tarrytown, New York

Many people don’t realize that Sleepy Hollow is a real place you can visit. In fact, North Tarrytown changed it’s name in 1990s to increase tourism. We often get asked for recommendations for what to see and do in the Hollow and you can find our favorite local haunts in our Sleepy Hollow Travel Guide.

We asked our friends at the Sleepy Hollow Historical Society how Washington Irving was influenced by this secluded glen and how Sleepy Hollow became famous because of him writing the Legend.

-Washington Irving wrote two amazing Hudson River valley tales that drew on the Dutch influence on early America. “Rip Van Winkle” was set in the Catskills while “The Legend of Sleepy Hollow” was set right here. When he arrived in the Tarrytown area for a stay at age 15, he found a warm reception from the locals because of his connection to the Paulding family (his older brother William had married Julia Paulding), an influential family whose heroism and sacrifice in the War earned them wide-spread respect. He listened to the people he met, pulling through their love of gatherings, feast and folklore into “The Legend.”

-Only 15 years had passed since the end of the Revolutionary War and the creation of a new country. Irving was able to hear first-hand from men and women who had lived through the war, and heard them talk on a personal level about those who were not so fortunate. In addition, Irving forged a lifelong friend and writing partner in James Kirke Paulding during that summer of 1798. 

-Perhaps less known is that Irving returned to the Hudson River valley around 1810 after a great tragedy in his life. While still grieving the death of his fiancé, Matilda Hoffman, Irving sailed up the Hudson and spent time at the home of a friend in Kinderhook. While much of “The Legend” is lively and fun, there are some descriptive scenes that evoke a slowness… a sleepiness… that may have stemmed from that trip edged with melancholy. 

-We also know something about the area’s influence on Irving based on the fact that he decided to buy his first and only home right here, in Tarrytown. He could have lived anywhere, but found joy and fulfillment in transforming Wolfert’s Roost into his beloved Sunnyside. While he never married, Irving was surrounded by family and friends throughout his life. He is buried with many of his family in Sleepy Hollow Cemetery, a cemetery that he helped found, overlooking the Old Dutch Church of which he wrote.

SLEEPY HOLLOW BOOK CLUB | Discussion Questions (Part 2) | If you’re not a member yet, sign up for It’s a Charming Life’s newsletter.

• Do you see how Washington Irving was influenced by old Dutch folklore to create one of America’s greatest ghost stories?
• A big theme of the short story is superstitions: Do you believe Sleepy Hollow was/is truly haunted? Is that why it’s become a Halloween tourist destination?
• The Headless Horseman says so much for speaking so little. Who is your favorite character and why?

PART 3: Personal Connections, favorite quotes, and characters

Here is what reading “The Legend of Sleepy Hollow” for the Bicentennial did to us.

Jonas: Everytime I read it I cannot decide whether I am “Team Brom” or “Team Ichabod”. It is interesting how many different layers that are revealed to you in such a short story as it is for every year as you read it. The Headless Horseman is an immortal character, much because his face does not reveal his true look.

“His appetite for the marvelous, and his powers of digesting it, were equally extraordinary”

Lindsay: Having read the Legend almost every October for the last several years, something tends to stick out to me differently every time. For the Bicentennial Celebration I feel I admired more the longevity of Irving’s writing and how he brings all the characters to life in a short story. It amazes me that a Headless character can speak such volumes and still be a Halloween icon 200 years later. My favorite quote is:

“If ever I should wish for a retreat, whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.”

SLEEPY HOLLOW BOOK CLUB | Discussion Questions (Part 3) | If you’re not a member yet, sign up for It’s a Charming Life’s newsletter.

• What is your favorite quote from the Legend?
• Who is your favorite character and why?
• What do you think happened to Ichabod Crane?

Thank you so much for joining us in reading and celebrating the Bicentennial of “The Legend of Sleepy Hollow”, it was such a pleasure!
Bye For Now,
Lindsay & Jonas