Southampton Trails Preservation Society
SOUTHAMPTON TRAILS PRESERVATION SOCIETY
We Are A 501(C)(3) Not For Profit

P.O. Box 1171
Bridgehampton, NY 11932

info@southamptontrails.org
Walking Tour of Sag Harbor

Generously Contributed by Ken Kindler
On Sunday, Tony Garro, of Southampton Trails Preservation Society lead a “hike/walking tour” of Sag Harbor.  This is one
of Tony’s favorite “hikes” and he leads it with some regularity.  On this walk, you get to see historic Sag Harbor.  There are
many lovely hikes to take in the woods with STPS as well. Check www.hike-li.org for ongoing listings.

I parked on Long Wharf, where I met Tony who was very graciously providing me with a private walking tour this day. We
walked back towards the Wind Mill and headed east along Bay Street.  The Wind Mill that sits at the foot of the Wharf serves
as an information center for visitors.  The Wharf was the center of economic activity in Sag Harbor in 1770 when the first
section of the 1000-foot Wharf was built.

During WWI and WWII many war materials were manufactured in Sag Harbor. The Bliss Torpedo Co. manufactured
torpedoes for the US Navy here.  Now a whole complex of stores and businesses occupy this building.  The Bliss Torpedo
Testing Station Corner Stone, dated 1891-1925, can still be seen at this complex.  Grumman Corp. later occupied this space
where it built parts for jets and components of the Lunar Excursion Module (LEM).
Tony normally begins his tour by the Wind Mill.  To get the Wind Mill, turn left onto Bay Street.  Public Restrooms (in a grey
building right after the long brick building) are visible as soon as you make a left turn off of Long Wharf.  

Bay Street is actually man-made land; it stands now where the Bay used to be. Marine Park is located between Bay Street
and the water.  Between1800 – 1860 what is now Bay Street was filled with whaling ships.  Tony pointed out a number of
homes across from the harbor that were B and B’s; no not Bed and Breakfasts, but rather “bars and brothels.”

While we were walking, I was amazed at the lovely and varied chorus of bird song that seemed to come from every
direction.  Although we were walking in “town”, Sag Harbor has the feel of a lovely walk in nature.

As we walked, we passed a plaque on Bay Street at the site of the first recorded settlement of Sag Harbor.  At that time, it
was named “Wegwagonock” meaning “at the foot of the hill.”  Dirt from Turkey Hill was pulled down to fill in the Bay Street
area. It was also used as ballast on the many whaling ships that sailed in and out of this busy port.

Many of the historical landmarks in Sag Harbor are private residences and may only be viewed from outside.  The first
residence we passed that was of historical interest was the
Captain John Phillips house (located on 67 Bay Street).  This was the home of the Phillips family from 1867 – 1947.  The
Captain was a renowned Sag Harbor schooner captain who ran sailing ships through the German blockades during WWI.

Tony and I then walked right onto the little used road, Dering Road, where there are a couple of “half houses”.  They are
three “bays” wide (the width of a window or a door) and have two windows and one door facing the street.  The builders of
these houses planned on buying the adjacent property and expanding the front of their homes to a normal width.  The
value of the adjacent land increased to the point where it was no longer affordable, so instead they built towards the back,
forming long narrow structures.

We continued south on Dering Road and turned right onto Rysam Street.  We were able to see the back of what was once
the Conkling farmhouse built around 1740, now incorporated into the Rysam-Sleight house.  The Conklings were patriots
during the Revolutionary War and the sons were privateer captains.

Between the buildings, Tony pointed out the back of the watchcase factory built in 1881 by Joseph Fahys at the corner of
Washington and Division Streets.  This building was bought by the Bulova Watch Company in 1937.

Heading south on Rysam Lane we passed Love Lane off to our right, so called since it was once a popular trysting place
for young lovers.

On the left (east) side of Rysam Street, as we approached Union Street, we found a plaque that reads “On this Spot Stood
an American Fort 1812.”   During the War of 1812, Turkey Hill was much higher than it is now and provided a commanding
view of the Harbor.  During the war, the fort’s cannons repulsed a British landing party.  Sag Harbor at the time was a
thriving seaport and the British coveted it.

We continued south on Rysam and found Rysam State Cemetery.  It is wedged between two houses; you would miss it
unless it was pointed out to you.

We then turned right onto High Street, traveled down High Street and made a right onto Hampton Street (CR 114).  On
Union Street, near Division Street we paused in front of the “1693 House” which was originally built in Sagaponack and
later moved to Sag Harbor.

Tony and I headed back north on Hampton Street and turned right on Union Street.  There we saw Saint Andrews Church
and several more “half houses”.  

As we turned right onto Church Street, Tony pointed in the direction of several nearby churches; the Methodist Church,
the Catholic Church, the Episcopal Church and the Whaler’s Church.  Near the corner of Union and Madison Streets by the
Whaler’s Church stands “The Old Burying Ground.”  The Cemetery is open to the public.  You can enter the Cemetery
through a break in the hedge along the walk to the church. During the hurricane of 1938 the186 foot church steeple was
blown over and landed in the cemetery.

On Union Street, next to the Whaler’s Church we paused by a memorial stone commemorating a heroic military operation
during the Revolutionary War.  During the early part of the war, things were going badly for the Americans.  There was a
British garrison and fort here that a small band of colonist troops overwhelmed in a daring raid.  This, Tony said, was a
boost in morale when the Americans really needed it.

We crossed over Sage Street and soon came to the David Hand House; has been moved four times. A major occupation in
this town seems to be the moving of houses.  It is amazing how many houses no longer are situated where they were
originally built.  Some have been moved as many as five times.   David Hand had many thrilling escapades. He was a
patriot who was captured and escaped from the British three times.  James Fennimore Cooper modeled his character,
Natty Bumppo in The Leather Stocking Tales after Captain Hand.

We traveled back down Church Street to turn right on Sage Street. We turned left on Madison, then turned right on Union.  
Here we rested on the steps of the house once owned by Captain Hulbert.  He was captain of the Sag Harbor militia, a
squadron of Minute Men.  It is believed by some historians that the 13 stars and stripes of their flag was used as a model in
designing the first American flag.

We then turned right onto Main Street and passed a Civil War Memorial and the Admiral Oscar Stanton House. Our tour was
done…look for more hikes (usually wooded ones) given by the Southampton Trails Preservation Society.