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Looking down South Street with Snouder’s on the left and the Moore’s building down the block
2. Fleet’s Hall
On this corner used to stand Fleet’s Hall built by Samuel Van Wyck around 1897
It was used for civic and social meetings, dinners, dances, concerts and Oyster Bay’s first movies
Following Van Wyck’s death in 1911 the building was torn down and a hardware store built
The hardware store burned down in 2005 and this new one was built in its place
3. Moore’s Building c.1891 and 1901
Original built as a single story grocery store by James Moore in 1891 the building burned in 1901.
Moore was able to save the original external red brick work and added two more floors to the building
The upper floors were offices and meeting rooms which were used by President Roosevelt’s staff in 1903
There were telegraph and telephone lines that connected directly to Washington DC and Sagamore Hill
Atlantic Steamer Fire Co. No. 1 c.1895
The original two bay Fire House can be seen to the left of the building
One of the earliest fire trucks was a Silsby Steamer
4. Oyster Bay Bank 1891
This was the first Bank in Oyster Bay and opened in 1891
Originally the building was raised up with a wide stairway leading to the front door
In the basement was a pool hall and a tobacco shop and on the second floor were offices
The Masons rented the top floor where they had their Matinecock Lodge
When Theodore Roosevelt became Mayor of NYC he rented the office on the second floor
It was during his time at this building that he joined the Oyster Bay Mason’s Matinecock Lodge
A few years later when Roosevelt became President he had his staff moved to the Moore’s building
5. Derby-Hall Bandstand
Built in 1981 this is a replica of the original Bandstand that was removed in 1930.
Theodore Roosevelt during his time as President used to give speeches from here
This Civil War cannon came from the USS R. R. Cuyler which helped blockade Florida during the war
It was unveiled and dedicated by President Roosevelt in 1903
6. US Post Office 1936
Designed by NYC architect William Bottomley the building is meant to be a mirror image of Town Hall
Artistes were hired to paint the interior along with a set of murals telling the history of Oyster Bay
Italian sculptor Leo Lentelli created terracotta panels and a bust of President Roosevelt
7. Oyster Bay Railroad Station 1889
First built in 1889 the station was expanded in 1901
8. Theodore Roosevelt Memorial Park
Theodore Roosevelt had said that he wished these cattle fields could be made in to a
place for the citizens of Oyster Bay to gather for fresh air, especially the less fortunate ones.
Following his death in 1919 plans for the park began and it was dedicated in May of 1929
11. Captain Kidd In Oyster Bay
In June 1699 Captain Kid wishing to avoid his muteness crew in New York City anchored off Oyster Bay
He sent a secret letter to his wife in the city letting her know of his location but it was found out.
He quickly fled the area but was captured a month later in Boston being sent back to England in chains
12. Wightman Memorial Baptist Church 1908
This is the oldest Baptist congregation in New York State and was founded in 1700
Like many other churches on Long Island it was occupied by British soldiers during the war.
In 1806 a new church was constructed to house the steadily growing congregation
By 1908 the second building was moved back and the current lager church erected in its place.
Second Baptist Church 1806
This is the second church which was built in 1806 and moved back when the new one was erected in 1908
Baptist Church Cemetery c.1720
This is the Baptist Church cemetery and was created on land donated by William Wright in 1720
The oldest headstone still legible is that of Martha Cooper who departed this life in 1749
13. Octagon Hotel 1851
First called Nassau House it was built by Luther Jackson in 1851 for political and social meetings
It was purchased in 1887 by Phillip and Mary Lavelle who renamed it the Octagon Hotel
It was the first building to have electric lights and its own direct phone line to NYC
When Roosevelt was Governor his secretary had an office here before moving to the Bank space
Charles Davenport was the last owner and sold it after ten years do to declining business
The building then housed various auto dealerships until recently being restored
14. The Printery 1889
16. Raynham Hall Museum 1738
17. Seely/Wright House 1830
18. Ludlam Building a.1848
19. Snouders Drug Store b.1884
20. Hood A.M.E. Zion Church 1856
The congregation was formed in 1848 and a wood frame church was built in 1856
By 1937 enough money had been raised to brick face the building and add electric lights
This is the oldest church group in Oyster Bay still using their original building
21. Earle-Wightman House c.1720
Originally a small one room house built c.1720 it was moved here around 1897
The building is named after two Baptist ministers that lived here at one point
In 1966 the house was donated to the town for use by the Oyster Bay Historical Society
22. St. Paul’s Methodist Church c.1891
The first Methodist group formed in 1812 and met at the Academy until they built a church in 1858
When the congregation moved in to this church around 1891 they sold the 1858 church to the Blacksmith
The bell tower over the door had been much higher but was hit by lightening in the 1920s and lowered
24. Oyster Bay Public Library 1901
This brick library was built in 1901 on the site of the original Peoples Library & Reading Room
Theodore Roosevelt laid the corner stone when construction began in 1899
The house on the right was built in 1890 and moved here and attached to the Library in 1975
25. Stoddard House 1893
This house was built by G. B. Stoddard in 1893.
For many years it held the Townsend Society of America and the Underhill Society of America
26. Oyster Bay High School 1929
This school was built in 1929 to replace the first High School built in 1901 a few blocks west
Some of the new modern features included a PA system and central vacuums
In 2000 the school got a new updated library and gymnasium
27. The McCoun House c.1842
Mrs. McCoun received two acres of land from her father to build a summer hom on
The main center house is original to 1842 and the front porches were added in 1921
At some point it took on the name Hillside and may have been used as an inn or tavern?
28. Wilson House c.1750
This house was built in the 1750s and still sits on its original foundation.
The house is named after Harry Wilson who was a barrel maker and lived here for many years
There is a legend that George Washington stood on the front porch and spoke to a group of children
29. First Presbyterian Church of Oyster Bay 1872
The First Presbyterian congregation was formed in 1842 and occupied various buildings at first
In 1872 Pasture Benjamin L. Swan was able to get land and then helped to build this church
It was designed by the architect J. Cleveland Cady who would go on to create amongst other things
The Metropolitan Opera House and The Museum of Natural History
Theodore Roosevelt attended this church with his parents and his father’s funeral was held here
30. Christ Church of Oyster Bay c.1870s
Other churches occupied this spot over the years until this one was constructed in the 1870s
Originally a wood structure the building was enlarged and encased in stone in 1925
President Roosevelt and his family attended church here and it is also where his funeral was held
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