Port Jefferson

Roe House
118 West Broadway
Built in 1682, the John Roe House is saltbox in design and stood at the edge of the saltmarsh. John Roe, a shoemaker and the first resident of Drowned Meadow, lived in the house. It was moved in 1896 to a location near the railroad tracks where it served as a bar for the trainmen after working hours. The house was moved to its present site in 1982 and now serves as a community information center, maintained by the Greater Port Jefferson Chamber of Commerce.
Marina and Ferry Dock
The Mather Shipyard and docks were located here. The Mather family built some 54 vessels, including the Martha E. Wallace (half-hull is in the Mather Museum) which was the largest sailing vessel built in Port Jefferson. The original Nonowantuc and Park City, two of the earliest ferries to run between Port Jefferson and Bridgeport, were also built by Mather. The ferry line has been in continuous operation since 1883, and one of the founders was P.T. Barnum.
Thomas Jefferson Statue
The village was named after Thomas Jefferson at the urging of shipbuilder Elisha Bayles, an ardent Jeffersonian Democrat. Jefferson helped the village acquire funds for dredging of the harbor channel. The statue, dedicated on July 4, 1994, was sculpted by Domenico Facci.
The Sailor
Waterfront Park, Danfords
This statue was once part of a triumverate of a sailor, soldier and marine on a New England public building. It was dedicated in 1984, "In recognition of the shipbuilders who from the late 1700s launched over 400 vessels to answer the call of country, commerce, whaling and pleasure." The dedication line on the statue is from John Masefield's poem Sea Fever.
Danfords — Bayles Dock
25 East Broadway
The inn was built in 1986 and incorporated some existing structures. The west end, built in 1870, has been a blacksmith shop, boxing emporium, social club, ice cream parlor, paint store and lastly, a gift ship owned by Mary Bayles. The 1938 hurricane blew out the back of the shop but strangely left the crockery on the shelves. The dock is Bayles Dock.
Potter Doorway
End of Bayles Dock
Note the architectural detail of the Palladian door surround on the southeast corner of Danfords. The doorway was saved from the Potter Mansion in Smithtown before the mansion was demolished.
Hill Climb Plaque
Danfords driveway exit and East Broadway
Many automobile hill climbing contests were held going up East Broadway from 1910 to 1925. Two of the cars that raced, the Only (1910) and the F.R.P. (1916) were built in Port Jefferson. Henry Ford's entry raced in the 1910 and 1911 races and placed 16th and 17th. In 1925, the F.R.P. defeated the Pike's Peak Hill Climb winner, proclaiming the F.R.P. the best car in the country.
Bayles Chandlery
101 East Broadway
The Chandlery carried a full stock of ship's stores and supplies. It was part of the Bayles Shipyard. This building, one of the last two standing 19th century structures on the waterfront, was built in1897 to replace the original chandlery that burned in the waterfront fire of that year. It is recognized as worthy of preservation for its "quality, uniqueness and history as one of the best remaing examples of its architectural period."
Bayles Shipyard Site
North of Chandlery
Three generations of the Bayles family built over 140 wooden ships between 1830 and 1917 in this now open area. Cargo vessels, whale ships and fine luxury yachts were built here. Bayles Dock and the Chandlery were part of the shipyard.
Bell — Hulse House
102 East Broadway
Capt. Thomas Bell, the original owner built three sloops and a gunboat for the U.S. Navy between 1802 and 1817. Lewis Hulse, the second owner, built seven ships and was one of the first merchants in the village. The Colonial style (circa 1802), with later additions, has a transom with side lights around the doorway. The pediment on the wrap around porch with dentil molding faces the harbor. Note the turned wood spindles on the porch balustrade with hanging pendants.
"Bucket of Blood"
116 East Main Street
Like every seaport village, Port Jefferson had its gin mills, and this now quiet store was the site of the local "watering hole" during the shipbuilding days. The real name was the "Holbrau." It became Greg Grammas' Sweet Shop and Ice Cream Parlor during World War I then an antique store.
G.W. Brewster House
109 East Main Street
George Washington Brewster, born in 1822, was the captain of the James M. Holmes, a trading vessel. He built this shingled house (circa 1853). He died on a seafaring voyage in 1878 and is buried in Santos, Brazil. Many Port Jefferson seamen died during long voyages and were buried at sea of in foreign lands.
Cookie Hill
111 East Main Street
This beautiful wrought iron gate leads to the Elisha Bayles house. The original center section is said to date from near 1800. James Madison Bayles (son of Elisha) was born here in 1815. He became the leading shipbuilder of the Bayles shipbuilding family, which owned the house until 1950. According to family legend, a Bayles wife baked and sold cookies to make a living while awaiting the return of her seafaring husband, hence the name "Cookie Hill."
Selah Hulse House
126 East Main Street
First recorded in a 1765 deed, this house stood on the edge of Drowned Meadow. The owner could go out of his back door on the lower level, board his boat and enter the bay. This house was plundered during the Revolutionary War. A set of French maritime naval maps from the 1700s was found in the attic during a recent renovation. The only missing chart was that of the Long Island waters.
The Heesch Building
128 East Main Street
Built in 1897, this building housed offices in 1910. By 1917 an oven was installed , and it became a bakery and candy factory operated by the West family. Mrs. Heesch ran an antique shop there for many years, and Oscar Heesch served as a policeman in Belle Terre.
First School Site
119 East Main Street
The original schoolhouse (circa 1820) stood here. It was a seven by nine foot structure located on the northeast corner of Thompson Street and East Main Street. The building no longer exists.
Good Times Book Store
150 East Main Street
Built in 1848, this building was originally a butcher shop. It became Saxton's Shoe Store and then a book store. The Italianate brick building has a Greek Revival broken pediment on the roof line.
Library
100 Thompson Street
The library was established in 1909 with a small collection on the upper floor of a store located on the corner of East Main Street and East Broadway. It moved several times before settling at Thompson Street (1924) in the building designed by Mike Stillman. It is Colonial Revival in style with three columns on each side of the Federal doorway. Additions were made in 1942, in 1967 and again in 1997. It serves the community well with 111,000 volume, 12,000 audio visual materials and 6,000 non-book items.
Millinery Shop
156 East Main Street
This late 19th century Italianate building has beautiful ornamental double bracketry under the eaves. It was once a millinery shop.
1812 House
205 East Main Street
The south wing (circa 1812) is the original house structure built by Beriah Petty for shipbuilder Thomas Bayles, brother of Elisha Bayles of "Cookie Hill." It is a sister house to the Cookie Hill house. The beautiful doorway is Georgian Colonial in detail.
The Knitting Cove
206 East Main Street
The arched door with bead and reel molding in one of the prettiest doorways in Port Jefferson. The south part of the building was added in 1910 as a telephone office.
W.L. Jones House
220 East Main Street
Capt. William L. Jones was an early shipbuilder who initiated businesses on East Main Street by filling in part of the tidal Drowned Meadow (circa 1836). The two-storied Adam style brick house with 6 over 6 shuttered windows and decorative moldings under the eaves was the O.B. Davis Funeral Home for more than 50 years.
Temperance Hall
311 East Main Street
This building was the site of several fraternal organizations over the years and was the center for the local temperance movement during Prohibition (1919-1933).
Baptist Church
East Main Street and Prospect Street
The church was built by the Congregationalists in 1855 who sold it to the Baptists in 1861. The steeple was a landmark for captains who were looking for the Customs House located in front of the church when Port Jefferson was a Port of Entry from August 31, 1852 to the late 1880s.
Site of the Customs House
A small, wood-frame customs house stood in front of the Baptist Church , separated from the church by a narrow wagon road. As much as 30,000 tons of goods passed through customs annually with a peak enrollment of 239 ships in 1875. The Customs House was moved to Myrtle Avenue where it is now a private residence.
R.H. Wilson House
104 Prospect Street
Reuben H. Wilson, sailmaker, built this (circa 1840) home which was raised in the late 1800s for a first story addition. Wilson made sails for the America, the vessel that won the first America's Cup in 1843. His bird's wing shaped sail revolutionized sail making for all time. His sail loft was on East Broadway next to the Mather Ship Yard.
Edward Tooker Home
105 Prospect Street
Edward, the son of Hamilton Tooker, built this High Victorian Italianate (circa 1854). It is an eye-pleasing house with a low pitched roof. It has widely overhanging eaves featuring elaborate decorative double brackets, arched paired windows in the peak and double arched doors. The shuttered windows are a common New England feature of this style.
Hamilton Tooker Home
108 Prospect Street
Hamiliton Tooker was a boatman, a merchant, and a nurseryman in the 1850s to 1870s. This Federal style house (circa 1854) features unique swan bracketry under the eaves.
Capt. C.E. Tooker Home
114 Prospect Street
(circa 1852) Capt. Charles E. Tooker, along with P.T. Barnum and others, was a founder of the Bridgeport - Port Jefferson Steamboat Company in 1883. Tooker was a captain on the first ferries.
Billy Brown Residence
116 Prospect Street
Built by Joshua Kinner, this house (circa 1850) was bought by Billy Brown in 1869. Billy Brown ran a horse drawn stage service to the train station and to Patchogue and hauled machinery for the shipyards in his horse drawn freight wagon. Billy Brown was well known around the village.
J.R. Mather Home
115 Prospect Street
John Richard Mather built this house after Prospect Street (formerly named North Street) was laid out in 1840. The Mather Ship Yard built some 54 vessels. Mather's son, John Titus Mather, left money for John T. Mather Memorial Hospital, built in 1929. The house is presently a museum run by the Historical Society of Greater Port Jefferson.