Walking Tours

This is a sample of a few places and
buildings in the Pine Hill Historic
District which might be of interest to
you. The first three stops represent
Pine Hill’s beginning days in the early
1800s, few traces of which remain.
The second three stops are notable
examples of Pine Hill’s interesting
architecture.

Part 1
Early and Vanished Pine Hill

Stop 1
Old Turnpike Road/Ulster and
Delaware Turnpike
Early to mid-1800s and before
Old Turnpike Road is a vestige of a
colonial-era road that led from
Kingston up through the Esopus
Valley over Highmount into what was
to become Delaware County. The old
road was illustrated on a 1773 map
by surveyor William Cockburn. In
1802, a project to pave it was
launched, which finally saw
completion in 1850. Heavy hemlock
planks were used. Alf Evers wrote in
his book,The Catskills, “In its heyday
during the 1850s and 1860s, the
smooth plank road was one of the
wonders of its part of the Catskills.
During the 1890s, W. Abram
Hoffman, Kingston editor, recalled
that at one time it had not been
unusual to see fifty teams following
closely behind each other on the
plank road. Seven tanneries in
Shandaken and five across the Pine
Hill in Delaware County used
the road.”

Stop 2
307 Main Street
Pine Hill Tavern/Glen Hall/
Colonial Inn
Oldest part, c. around 1810
The Colonial Inn location is thought to
be the site of Pine Hill’s first clearing
and settlement, made by Aaron Adams
shortly after 1800. He operated a
sawmill and “Pine Tavern” there.
Between 1800 and 1810, Adams built a
hotel on the site and continued to
reside there, until about 1816 when he
moved away. There are conflicting
accounts about this early building.
Some believe it is subsumed within the
present Colonial Inn. The larger portion
of the Inn went up in 1874 and was
called Glen Hall.

Stop 3
Pine Hill Road, Old Route 28
Methodist Cemetery
Dates from mid-1800s
The oldest headstones in this cemetery
include that of Mary Smith, b. January
24,1788; d. December 3, 1866, and
“Alice, daughter of Nathan and
Catharine Peet,” who died January
20, 1849.

Part 2
Pine Hill Architecture

Stop 4
26 Academy Street
Shandaken Historical Museum/
School House No. 10
c. 1924, Colonial Revival and
Craftsman styles
The former school, which houses the
Shandaken Historical Museum, exhibits

the eclectic Colonial Revival and
Craftsman architectural styles that
came into vogue at the beginning of
the 20th century.

Stop 5
22 Elm Street
Morton Memorial Library
c. 1903, Colonial Revival style
One manifestation of Pine Hill’s
prosperity at the turn of the 20th
century is the Morton Memorial Library.
It was constructed in 1903 and stands
out as a preeminent building due to its
masonry construction, in contrast to all
the wood-frame buildings that make up
the majority of the hamlet. The rusticated
stone of its walls, slate roof, and
columned entrance contribute to make
it the finest building in Pine Hill.The
building was initially funded by a
donation from Dr. Henry Samuel
Morton, Sr., the first president of the
Stevens Institute in Hoboken, in memory
of his late wife Clara. Dr. Morton died
in 1902, and his children completed the
project. The Mortons were long-time
summer residents with a grand cottage
west of the hamlet. The library building
was listed on the National Register of
Historic Places on February 21, 1997.

Stop 6
270-272 Main Street
Elbert Smith Drugstore
c. 1900, Colonial Revival style
This building has kept its appearance as
a former druggists’ store, originating
with William and Elbert Smith. A ruby-colored
stained glass above the entrance reads Smith Bros. Druggists.  The drugstore building dates
from around 1900. Note the massive scroll
sawn brackets of the porch.