The Dowager’s Diary: Week One Hundred and Seventy-One

June 1-8, 1918

“Temperature went over one hundred degrees.  To Red Cross Canteen in morning to meet Dorothy who was volunteering at the soldier’s debarkation canteen at Penn Station. Then onto Sea Bright, New Jersey to see about purchasing the Romaine Cottage near Black Point in nearby Rumson for Dorothy and her sons.Then she and I back to New York City then onto the Sleepy Hollow Club for dinner and Comedy Club performance in beautiful open-air theater.Home to 35 East 30th Street in the wee hours.”

Tea on the Lawn at Sleepy Hollow, 1914

Those two Roosevelt gals were quite the gad-abouts.  In a little more than twenty-four hours they went from New York City down to the Jersey Shore and back to New York City before finally flitting up to the Hudson Valley to have dinner and see a show at the Sleepy Hollow Country Club. Traveling by “motor” as Kate Roosevelt referred to her Buick touring car, mother and daughter didn’t let the soaring temperature stop them. In those days the only air conditioning in cars came from rolling down the windows or folding down the canvas top.

Sleepy Hollow Clubhouse, 1912

By the time they arrived at their destination, it was sunset.The cool breezes along the Hudson River and strolling through a beautiful clubhouse and made for a lovely evening. The Sleepy Hollow Country Club was founded in 1911. Its clubhouse, known as Woodlea, a one hundred and forty room mansion, was once-owned by Colonel Elliott Fitch Shepard and his wife, Margaret Louisa Vanderbilt Shepard. It was one of the largest privately-owned houses in the United States.

Elliott Shepard

Woodlea was designed in 1892 by the architectural firm of McKim, Mead and White. It cost two million dollars to build (fifty-five million dollars in 2018). The mansion was designed in an Italian Renaissance Revival style with dabs of Beaux-Arts details. With a view of the Hudson River, it was the perfect place to entertain and unwind on a sultry summer night.

Margaret Vanderbilt Shepard

By the time Kate and her daughter, Dorothy arrived there on June 1, 1918, the clubhouse and grounds had passed through several hands and gone through many phases of reconstruction.

Sleepy Hollow Golf Course

Sleepy Hollow’s clubhouse began as a private residence named Woodlea. The mansion retained the name its first owner, J. Butler Wright gave it.  It dates to around 1806 and was originally a Victorian style home made of painted brick with porches and a high tower. Various farms made up the property. In the early 1890s, Colonel Elliott Fitch Shepard purchased the house and its surrounding five hundred acres. He soon began renovations and improvements to the home and grounds. To do so, he had a dock constructed nearby so that construction materials could be shipped to the property.  Shepard died in 1893, leaving his widow, Margaret to oversee completion of Woodlea. In 1896, Maria Louisa Kissam, Margaret’s mother and widow of William Henry Vanderbilt died in the house. With only bad memories and high maintenance, Margaret sold the estate in 1906 to New York businessman, Archibald S. White for one million dollars. He bought it as a present for his wife Olive Celest Moore White. In 1910, the couple sold the estate to Frank Vanderlip and William Rockefeller at a loss. Mrs. Narcissa Vanderlip thought the home too big to live in so the partners assembled a board of directors that included future Titanic victim, John Jacob Astor; the railroad tycoon, Averell Harriman; Cornelius Vanderbilt III and Harrison A. William to form a country club. The Sleepy Hollow Country Club was incorporated in 1911 with six hundred original members. Initiation and yearly dues came to two hundred dollars, offering members the opportunity to play on a golf course professionally designed by the Scotsman, Charles B. Macdonald and Seth Raynor and enjoy an outdoor garden theater surrounded by sculptured cedar trees and a sixteenth-century Italian portal planned by the sons of Frederick Law Olmsted.

Outdoor garden and theater at Sleepy Hollow, 1906

From the diary entry dated, June 1, 1918, it sounded like Kate Roosevelt and her daughter, Dorothy Roosevelt Geer, had a delightful evening admiring the grounds and grand house that encompassed the Sleepy Hollow Country Club and were most certainly impressed by the names associated with its history. Averill Harriman, one of the founders was a family friend. He and his daughter, Mary Harriman and the Roosevelts had been friends for years; the apartment building that Kate Roosevelt lived in was designed by Stanford White’s architectural firm, McKim, Mead and White, and Central Park where she often went for carriage rides was designed by Frederick Law Olmsted.

Sharon Hazard’s Dowager’s Diary appears on Thursday.

On WAT-CAST, listen to Sharon talk about the series.

Photo One:
Club Members arriving at Sleepy Hollow
1914
Suburban Life

Photo Two:
Tea on the Lawn at Sleepy Hollow, 1914
The Suburbanite

Photo Three:
Sleepy Hollow Clubhouse, 1912
Monolith of the Work of McKim, Mead and White

Photo Four:
Elliott Shepard
Notable Americans 1893

Photo Five:
Margaret Vanderbilt Shepard
San Antonio Museum of Art

Photo Six:
Sleepy Hollow Golf Course
The Chesterfieldian, public domain

Photo Seven:
Outdoor garden and theater at Sleepy Hollow, 1906
Notable American Homes