Sagamore Hill National Park Service 

U.S. Department of the Interior 

Sagamore Hill 

National Historic Site 

Old Orchard
 

“It had always been the family plan for Ted to inherit Sagamore 

Hill...By 1937 we had been married twenty seven years and were 

tired of living here and there in rented houses.” 

—Eleanor Alexander Roosevelt L to R: TR III, TR Jr., William McMillan, Grace Roosevelt McMillan,

William McMillan, Jr., Eleanor A. Roosevelt, Cornelius, Quentin II 

Old Orchard Theodore Roosevelt, Jr. (Ted) and his wife Eleanor 

Alexander Roosevelt built the house they called “Old 

Orchard” in 1937-1938 on four acres of land purchased from Ted’s mother in the Sagamore Hill apple 

orchard. The Georgian style home was designed 

by their son-in-law, Baltimore architect William G. 

McMillan, Jr. to Ted and Eleanor Roosevelt’s satisfaction. The Old Orchard compound also included 

a multi-bay garage for the family’s automobiles; a 

cottage for the site foreman and a cold storage all 

located within close proximity to the home. 

The house was built of brick and intended to be 

painted white, but left exposed because they found 

the color to be “so good” wrote Eleanor A. Roosevelt. Instead the doors, shutters and trim of Old 

Orchard were painted an off –white. The exterior 

brick would eventually be covered in English ivy, 

which remained until the National Park Service 

acquisition in 1962. 

Main Floor 

View of the entrance hall 

The elegant home was filled with mementos of 

world travel, including Chinese furniture collected 

by Eleanor in the 1920s as well as reminders of Ted’s 

service in the infantry during World War I. The large 

eighteenth-century front door was found in the back 

yard of a parish in Dublin by Ted and Eleanor. 

The entrance hall to the home was lined with family 

portraits dating back four generations, and some of 

Ted’s flags, including those from his governorships 

and of other prominent positions he held. Ted shared 

his father’s love of reading, and Eleanor stated that 

“books...have overflowed into every room in the 

house, both upstairs and down.” 

Eleanor referred to the inside of the home as her 

province and wanted color everywhere. Some rooms 

had a color theme—the drawing room, “happily 

combined every shade of red from deep crimson to 

pale rose”—while others were filled with items from 

a trip to China, gifts from family and friends and 

other family treasures. 

View of the drawing room 

Second Floor The upstairs was home to the family’s bedrooms— 

one for Ted and Eleanor and one each for their sons 

Quentin and Cornelius (their daughter Grace and 

son Theodore III had moved out years earlier)—as 

well as one for their maid and two spare rooms. As 

was typical in some English country houses at the 

time, the Roosevelts decided to name some of the 

bedrooms in their home, with names as exotic as 

“Chengtu,” after Quentin’s interest in China or as 

American as “Vermont,” after the state where some 

of the furniture in Ted and Eleanor’s room was 

purchased. 
 

Theodore Roosevelt Jr. & 

Eleanor Butler Alexander 

Eleanor Butler Alexander was born in New York’s 

Upper East Side to Henry Addison and Grace Green 

Alexander in 1888. Although a native New Yorker, 

Eleanor spent the first years of her life on the move, 

living in California and Paris, France for a period of 

six years. She returned to the United States in 1900. 

Eleanor and Ted had several encounters at social 

functions since Eleanor was acquainted with Ted’s 

younger sister Ethel. The two were married in New 

York City at Fifth Avenue Presbyterian Church on 

June 20, 1910. Together Theodore and Eleanor Roosevelt had four children: Grace, Theodore III, Cornelius and Quentin II (named for Ted’s baby brother 

who was killed during the First World War). Eleanor A. Roosevelt and Theodore Roosevelt, Jr. 

The Great War	 During the First World War, Theodore Roosevelt, Jr. 

developed a reputation as a successful soldier and 

leader. Lt. Colonel Roosevelt participated in the Allied offensive at the Somme in 1918. He received the 

Distinguished Service Cross and the French Croix 

De Guerre for his valor. Eleanor, determined to be 

close to her husband, headed to France to work with 

the Young Men’s Christian Association (YMCA). 

At the YMCA, Eleanor taught French to offi cers of 

the American Expeditionary Force, redesigned the 

ladies YMCA uniform to be more practical, and in 

the Paris Office, she assigned newly arrived women 

to leave areas. After the war General Pershing issued 

Eleanor a citation for her work. As the war wound 

down, Ted and other like-minded American soldiers formed the American Legion to carry forward 

the camaraderie and spirit of the doughboys into 

civilian life. 

Interwar Period	 After the war Ted launched his public career in 1919 

as a member of the New York State Assembly in the 

2nd Assembly District of Nassau County. His career included the positions of Assistant Secretary of 

the Navy, Governor of Puerto Rico and Governor 

General of the Philippines. He wrote books about 

his experiences in the Great War, his expedition to 

China, and his family life. 

Eleanor was never far behind: she even found her 

way to Asia during both of his expeditions. Later, 

Ted worked as a publisher for Doubleday and as 

chairman of the board of the American Express 

Company. Eleanor held the post of the president of 

the Girl Scout Council of Greater New York from 

1937-1942. 

The Second World War & 

Afterward 

In the emerging crisis of World War II Ted held the 

position that the United States should stay neutral. 

However, leading up to the attack on Pearl Harbor, 

Ted regained his old command of the 1st Division's 

26th Infantry Regiment, and later was promoted to 

brigadier general and deputy commander of the 1st 

Division. He fought throughout the North African 

campaign and participated in the invasion of Sicily. Eleanor, once again determined to be close to 

her husband, took a position with the American Red 

Cross in England. 

A seasoned combat veteran, General Roosevelt 

played a critical role in the D-Day invasion. Due to 

an unexpected current and the confusion of battle 

on Utah Beach, the first troops landed nearly a mile 

away from the planned landing zone. By making the 

spot decision “We’ll start the war from here” and improvising the orders for all successive landing waves, 

Roosevelt made order from chaos. Five weeks later, 

on July 11, 1944, Ted Jr. died of heart failure during 

the Allied drive across France. He was awarded the 

Congressional Medal of Honor posthumously. 

Eleanor was quite active during the remaining years 

of her life. Following Ted’s death, she continued 

her involvement with the Women’s Auxiliary Corps 

(WAC). Eleanor succeeded in getting a newly formed 

WAC company of medical technicians named in 

honor of her late husband. After returning to the 

United States, she worked with women’s veteran 

groups and continued to be involved with the Girl 

Scouts. One of Eleanor’s final accomplishments was 

the completion of her memoir in 1959, Day Before 

Yesterday, which was used as a source for the production of this brochure. Eleanor lived at Old Orchard until her death in May 1960. 

Eleanor A. Roosevelt with pet monkey outside of Old Orchard 

Theodore Roosevelt 

Museum at Old Orchard 

The Theodore Roosevelt Association purchased the 

home and donated it to the National Park Service 

in 1962. First opened to the public as a museum in 

1966, the museum features three exhibit areas and a 

video theater on the fi rst floor. The exhibits can be 

divided into three themes. The first room focuses on 

Theodore Roosevelt’s early life, beginning with his 

childhood and through his time as Governor of New 

York. The second room is devoted to his presidency, 

with special attention to his foreign policy and conservation efforts. The third room explores his postpresidential years, including his African safari and 

his 1912 campaign as a third party candidate. 

About Sagamore Hill Sagamore Hill National Historic Site is a unit of 

the National Park Service. The site was established 

by Congress in 1962 to preserve and interpret the 

structures, landscape, collections and other cultural 

resources associated with Theodore Roosevelt’s 

home in Oyster Bay, New York, to ensure that future 

generations understand and appreciate the life and 

legacy of Theodore Roosevelt, his family and the 

significant events associated with him. The 83 acre 

site also protects significant natural areas including 

woodlands, pastures marshlands and a beach. 

For More Information: 

Sagamore Hill NHS 

20 Sagamore Hill RD 

Oyster Bay, NY 11771 

Ph. 516-922-4788 

www.nps.gov/sahi