Place

Oyster Bay, New York

Octagon Hotel
The Octagon Hotel in Downtown Oyster Bay

NPS/Sagamore Hill Collection Archives

Quick Facts
Location:
Oyster Bay, NY
Significance:
Location of Sagamore Hill
Since its settlement in 1653, Oyster Bay has had a rich history as a colonial settlement, ship building center, and as a hub for spy activity during the Revolutionary War while under British control. In the 1800’s, Oyster Bay was a popular summer destination for wealthy New York City families. In 1902, the area was brought to national attention when the 26th U.S. President Theodore Roosevelt, created the first “Summer White House,” having moved the executive office and staff from Washington, D.C. to Oyster Bay for the summers of 1902-08.

Roosevelts have lived in Oyster Bay since the 1860’s. As a child, Theodore Roosevelt's father rented a house in the area named Tranquility, where the family spent their summers. In 1885, TR built his home, Sagamore Hill, two and a half miles east of the village center, which he and his family frequented for goods, services, transportation and business. Today, Oyster Bay boasts sites and buildings in the village connected to Theodore Roosevelt, as well as memorials erected in tribute to Oyster Bay’s most beloved and famous resident. We encourage you to take a trip back in time and stroll the historic village to learn more about Theodore Roosevelt’s Oyster Bay. 

Oyster Bay Long Island Railroad Station


Foot of Audrey Avenue

The historic railroad station was built by the Long Island Railroad in 1889 and actively served the town until 1999. As New York City Police Commissioner between 1895 and 1897, Roosevelt regularly commuted from Oyster Bay into the city. Later, President Roosevelt would often travel to and from Washington D.C., by rail using this very train station. The station has been designated a Town of Oyster Bay Landmark and is on the National Register of Historic Places.

Derby Hall Bandstand


Shore & Audrey Avenue

Located in a small triangle between Oyster Bay Town Hall and the U.S. Post Office, it is here that Roosevelt often addressed the people of Oyster Bay, most notably during Independence Day celebrations. Time and weather took their toll on the original structure: it fell into disrepair and was razed. As a memorial to TR's daughter, Ethel Roosevelt Derby, her godson, retired Congressman Leonard Hall, raised funds for its reconstruction and it was dedicated in 1981. Since Hall died during its construction, the name was changed to honor both Mrs. Derby and Congressman Hall. It is flanked by three Civil War-era cannons, one of which was presented by the Navy to the town and unveiled by Theodore Roosevelt years eariler in 1903.

Oyster Bay Bank


20 Audrey Avenue

Built in 1891, this 3 ½ story building was the first bank built to serve the hamlet. The second floor of the building served as Roosevelt's Oyster Bay office while Governor of New York. In the summer of 1902, it served the same function for his White House staff. Between the 1890’s and 1924, the third floor was used as the Matinecock Lodge (#806) by the local chapter of the Masons. In January 1901, TR was inducted as a member of the lodge and attended meetings here throughout his life. In 1924, the lodge moved to the former Townsend Inn at 14 West Main Street. Roosevelt’s son, Theodore Roosevelt Jr., was active with the Masons at this location after his father’s death. Unfortunately, the historic Townsend Inn building burned in 2003. A similar style building was reconstructed on the site and it continues to serve as a Masonic Lodge.

The Moore Building


1 East Main Street

Built in 1891 by grocer James Moore, this building is one of the most prominent commercial buildings in the village. In 1902, it was expanded and the Queen Anne turret was added. In the summer of 1903, President Roosevelt's secretary William Loeb, noted its modern fixtures and its prominence at the commercial crossroads of Oyster Bay, and chose to rent office space here, moving from the Oyster Bay Bank Building. The offices were the base of operations for the “Summer White House” while TR was in town. Sagamore Hill connected to the Moore Building by telegraph and phone service. The building was also known as the “gate” because those interested in visiting the president needed to obtain permission through Secret Service agents who operated from there. The Moore Building is listed on the National Register of Historic Places and is a Town of Oyster Bay Landmark.

Christ Church


61 East Main Street

Roosevelt was brought up in the Dutch Reformed Church, but after marrying his second wife, Edith Kermit Carow, an Episcopalian, he and his family attended this church regularly throughout their lives and the Roosevelt family pew is preserved inside. When originally built in 1878, it was a wood building. In 1925, the structure was encased in stone.

Only a few miles from Sagamore Hill, Roosevelt once said, “The walk back from Church is almost as pleasant as the sermon itself.” He sometimes rowed Edith from the family beach around the tip of Cove Neck to attend this church. When Theodore Roosevelt died on January 6, 1919, his funeral was held at Christ Church with the procession heading east on East Main Street to Youngs Cemetery one mile from the church.

The First Presbyterian Church


60 East Main Street

As a youth, Roosevelt attended this church with his family when his father rented a summer home in Oyster Bay. Theodore Roosevelt’s father was an Elder at the Presbyterian Church at the time of his death in 1878. The carpenter Gothic-style church was built in 1873 and is listed on the National Register of Historic Places.

Snouder’s Drug Stores


108 South Street

Built in 1855 and expanded in 1890, this building had housed Snouder’s Drug Store since 1884. For many years, Snouder’s had the only telephone and switchboard in the village (beginning in 1887). Mr. Snouder would send staff members out on bicycles to deliver messages to the village households, including Sagamore Hill. In 1902, after becoming President, TR reluctantly allowed a telephone to be installed in the Roosevelt Home; the number was “OB 67.” The Roosevelt children often rode their ponies into Oyster Bay to visit the soda fountain at Snouder’s and get ice cream. This building is a Town of Oyster Bay Landmark.

Octagon Hotel


67 West Main Street

Built in 1854 as part of a mid-century movement to construct eight-sided structures that were said to be more conducive to healthy living because of increased light, ventilation and enhanced space, it was the only known “octagon” hotel at the time of its construction. The building was a popular gathering place for the upper class in Oyster Bay into the early 20th century. Over the years, Theodore Roosevelt was one of the hotel’s esteemed guests, visiting for business, political and social events. During his presidential years, visitors to the Summer White House often stayed here. The building served as a hotel until 1922. In subsequent years, its primary use was as a car dealership and automotive repair shop. In 2009, a private developer plans to rehabilitate the building as a mixed use development.

Sagamore Hill National Historic Site

Last updated: May 11, 2023