New York State Route199 (NY199) is a
state highway
A state highway, state road, or state route (and the equivalent provincial highway, provincial road, or provincial route) is usually a road that is either ''numbered'' or ''maintained'' by a sub-national state or province. A road numbered by a ...
located in the
Hudson Valley
The Hudson Valley (also known as the Hudson River Valley) comprises the valley of the Hudson River and its adjacent communities in the U.S. state of New York. The region stretches from the Capital District including Albany and Troy south to ...
of the U.S. state of
New York. Its western end is in
Ulster County
Ulster County is a county in the U.S. state of New York. It is situated along the Hudson River. As of the 2020 census, the population was 181,851. The county seat is Kingston. The county is named after the Irish province of Ulster.
History
...
, where it begins as the continuation of the short
U.S. Route 209 expressway east of its interchange with
U.S. Route 9W
U.S. Route 9W (US 9W) is a north–south U.S. Highway in the states of New Jersey and New York. It begins in Fort Lee, New Jersey, as Fletcher Avenue crosses the US 1–9, US 46, and the Interstate 95 (I-95) approache ...
; after crossing the
Kingston–Rhinecliff Bridge over the
Hudson River
The Hudson River is a river that flows from north to south primarily through eastern New York. It originates in the Adirondack Mountains of Upstate New York and flows southward through the Hudson Valley to the New York Harbor between N ...
the rest of the highway crosses northern
Dutchess County. As it does it passes through downtown
Red Hook and
Pine Plains, reaching its eastern end at
U.S. Route 44
U.S. Route 44 (US 44) is an east–west United States Numbered Highway that runs for through four states in the Northeastern United States. The western terminus is at US 209 and New York State Route 55 (NY 55) in Kerhonkson, ...
and
State Route 22 southwest of
Millerton in the upper Harlem Valley.
The portion of Route 199 east of its junction with the Taconic State Parkway was originally part of the
Ulster and Delaware Turnpike
Ulster (; ga, Ulaidh or ''Cúige Uladh'' ; sco, label= Ulster Scots, Ulstèr or ''Ulster'') is one of the four traditional Irish provinces. It is made up of nine counties: six of these constitute Northern Ireland (a part of the United King ...
, a toll road linking
Bainbridge to
Salisbury, Connecticut
Salisbury () is a town situated in Litchfield County, Connecticut, United States. The town is the northwesternmost in the state of Connecticut; the Massachusetts-New York-Connecticut tri-state marker is located at the northwest corner of the town ...
. This segment of the turnpike was incorporated into New York State Route41, a new route connecting
Barrytown to Millerton, in the mid-1920s. NY41 was renumbered to 199 as part of the
1930 renumbering of state highways in New York.
When the Kingston–Rhinecliff Bridge opened in 1957, NY199 was realigned to continue across the bridge to the town of Ulster. The former routing of the highway between Barrytown and
NY 9G along Barrytown Road remained state maintained until 1980, when ownership and maintenance of the highway was transferred to
Dutchess County. It is now designated as County Route82 (CR82).
Route description
Route 9W to Red Hook
The western terminus of Route 199 is the northern terminus of
U.S. Route 209 in
Ulster County
Ulster County is a county in the U.S. state of New York. It is situated along the Hudson River. As of the 2020 census, the population was 181,851. The county seat is Kingston. The county is named after the Irish province of Ulster.
History
...
. When the expressway section of the latter road reaches the
cloverleaf interchange
A cloverleaf interchange is a two-level interchange in which all turns are handled by slip roads. To go left (in right-hand traffic; reverse directions in left-driving regions), vehicles first continue as one road passes over or under the ...
with
US 9W
U.S. Route 9W (US 9W) is a north–south U.S. Highway in the states of New Jersey and New York. It begins in Fort Lee, New Jersey, as Fletcher Avenue crosses the US 1–9, US 46, and the Interstate 95 (I-95) approac ...
, in the town of
Ulster
Ulster (; ga, Ulaidh or ''Cúige Uladh'' ; sco, label= Ulster Scots, Ulstèr or ''Ulster'') is one of the four traditional Irish provinces. It is made up of nine counties: six of these constitute Northern Ireland (a part of the United King ...
, between
Kingston and
Lake Katrine, it assumes the 199 designation as it continues eastward through woodlands. Veering slightly northward, it has another interchange with
State Route 32 after a mile (1.6km), with the eastbound lanes reaching the toll gantry for the
Kingston–Rhinecliff Bridge further on.
West of the toll gantry, the expressway ends as the road narrows to two lanes to cross the bridge, on an east-southeast heading. On the east bank, now in the
Dutchess County town of
Rhinebeck, it remains two lanes as it traverses wooded areas, part of the
Hudson River Historic District
The Hudson River Historic District, also known as Hudson River Heritage Historic District, is the largest Federally designated district on the mainland of the contiguous United States.The Nantucket Historic District includes all of the island of ...
, a
National Historic Landmark
A National Historic Landmark (NHL) is a building, district, object, site, or structure that is officially recognized by the United States government for its outstanding historical significance. Only some 2,500 (~3%) of over 90,000 places listed ...
. The road returns to a due-east course shortly after the crossing; it has its first traffic light at the intersection with River Road (also
County Route 103).
At past that intersection, the highway reaches another traffic light at
State Route 9G. It joins that highway northbound, immediately entering the town of
Red Hook, for a two-mile (3.2km) stretch through woodlands, first heading northwest then due north.
The two lanes widen to four on either side of the
Rokeby Road intersection.
The 9G concurrency ends a mile to the north, where the roadway reaches another traffic light after a bend northeast. Here NY 199 turns east, going over a slight rise and then trending slightly southward towards the
village
A village is a clustered human settlement or community, larger than a hamlet but smaller than a town (although the word is often used to describe both hamlets and smaller towns), with a population typically ranging from a few hundred to ...
of
Red Hook. At the village line, a mile east of NY 9G, it passes Red Hook High School, the historic
Maizefield
Maizefield, often locally called Maizeland, is a historic house on West Market Street (New York State Route 199) in the village of Red Hook, New York, United States. It is a large plain brick building, in the Federal style, with clear English Ge ...
estate, and the middle school, becoming West Market Street. At the center of town, another traffic light marks the intersection with
U.S. Route 9
U.S. Route 9 (US 9) is a north–south United States highway in the states of Delaware, New Jersey, and New York in the Northeastern United States. It is one of only two U.S. Highways with a ferry connection (the Cape May–Lewes Ferry, between ...
.
Red Hook to Pine Plains
NY 199 becomes East Market Street and leaves the village approximately a half-mile (800m) to the east, curving gently through a mix of fields and
woodlot A woodlot is a parcel of a woodland or forest capable of small-scale production of forest products (such as wood fuel, sap for maple syrup, sawlogs, and pulpwood) as well as recreational uses like bird watching, bushwalking, and wildflower appr ...
s in the surrounding landscape. A mile (1.6km) past the village, the road makes the first of four crossings of the
Saw Kill. After crossing the
Lakes Kill
A lake is an area filled with water, localized in a basin, surrounded by land, and distinct from any river or other outlet that serves to feed or drain the lake. Lakes lie on land and are not part of the ocean, although, like the much larger ...
a thousand feet (300m) further on, the road starts a long turn southeastward past the former
Sky Park Airport and Red Hook Golf Club.
The Saw Kill crosses again just north of the end of this section, at the small hamlet of
Rock City, where the towns of Red Hook, Rhinebeck and
Milan
Milan ( , , Lombard: ; it, Milano ) is a city in northern Italy, capital of Lombardy, and the second-most populous city proper in Italy after Rome. The city proper has a population of about 1.4 million, while its metropolitan city h ...
meet.
State Route 308 has its eastern terminus here, and a signal over the third crossing of the Saw Kill regulates traffic as NY 199 makes the abrupt turn eastward again. A sculpture of an oversized fork marks this "fork in the road". The road and the Saw Kill parallel each other for another mile of rural landscape before the stream makes its final and uppermost crossing just past the Milan Hill Road (
County Route 54) intersection on the north side.
Past this point the highway bends southeast again, crossing
Little Wappingers Creek, as the landscape becomes hillier and more wooded. A mile and a half further it resumes heading east,
past Milan's town hall, to its interchange with the
Taconic State Parkway
The Taconic State Parkway (often called the Taconic or the TSP and known administratively as New York State Route 987G or NY 987G) is a parkway between Kensico Dam and Chatham, the longest in the U.S. state of New York. It follows ...
,
climbing slightly.
East of the Taconic NY 199 crosses the small hamlet of
Lafayetteville, turning to the north as it descends for a mile through a narrow, wooded valley to Wilbur Pond and Lafayetteville Multiple Use Area.
For the next two miles NY 199 continues to descend, turning northeast and entering the town of
Pine Plains midway. After crossing
Ham Brook, the highway turns north northeast for three-quarters of a mile (1.1km), bending back to the southeast around the side of an unnamed hill.
The road returns to an east southeast heading as it descends another mile and the hills abruptly give way to more level ground on the outskirts of central
Pine Plains,
where NY 199 passes Stissing Mountain High School and becomes West Church Street, still trending south.
Pine Plains to Harlem Valley
At the junction with Main Street in the center of town, the first traffic light since Rock City also marks where
State Route 82 comes in from the south. It forms NY 199's other concurrency when it joins the highway heading eastbound. The joined roads continue together east southeast back into the countryside for the next mile and a half. Just past Pine Plains' town hall, at Hammertown, NY 82 turns north, towards the
Columbia County hamlet of
Ancram, ending the concurrency.
From this intersection NY 199 turns northeast again briefly, then east, into a landscape of rolling hills, farms and woodlots. Three miles (5 km) of long curves in a generally eastward direction, climbing slightly, it reaches another small hamlet, Pulvers Corners, at an intersection with County Route 59.
East of there, the road drops briefly into a swampy area, then climbs again as it turns southeast. At the
North East town line, it reaches 1,000 feet (305m) above sea level, the highest elevation along its route.
NY 199 continues southeast down a narrow valley for its last to its eastern terminus, at
U.S. Route 44
U.S. Route 44 (US 44) is an east–west United States Numbered Highway that runs for through four states in the Northeastern United States. The western terminus is at US 209 and New York State Route 55 (NY 55) in Kerhonkson, ...
and
State Route 22 southwest of
Millerton.
History
Origins and designation
On April 2, 1802, the
New York State Legislature
The New York State Legislature consists of the two houses that act as the state legislature of the U.S. state of New York: The New York State Senate and the New York State Assembly. The Constitution of New York does not designate an official ...
created a turnpike corporation for the purpose of building a road—the
Ulster and Delaware Turnpike
Ulster (; ga, Ulaidh or ''Cúige Uladh'' ; sco, label= Ulster Scots, Ulstèr or ''Ulster'') is one of the four traditional Irish provinces. It is made up of nine counties: six of these constitute Northern Ireland (a part of the United King ...
—from the
Susquehanna River
The Susquehanna River (; Lenape: Siskëwahane) is a major river located in the Mid-Atlantic region of the United States, overlapping between the lower Northeast and the Upland South. At long, it is the longest river on the East Coast of the ...
in the vicinity of the town of Jericho (now
Bainbridge) to the
Connecticut
Connecticut () is the southernmost state in the New England region of the Northeastern United States. It is bordered by Rhode Island to the east, Massachusetts to the north, New York to the west, and Long Island Sound to the south. Its cap ...
state line at
Salisbury
Salisbury ( ) is a cathedral city in Wiltshire, England with a population of 41,820, at the confluence of the rivers Avon, Nadder and Bourne. The city is approximately from Southampton and from Bath.
Salisbury is in the southeast of Wil ...
. The portion of the Ulster and Delaware Turnpike east of the
Hudson River
The Hudson River is a river that flows from north to south primarily through eastern New York. It originates in the Adirondack Mountains of Upstate New York and flows southward through the Hudson Valley to the New York Harbor between N ...
was also commonly known as the "Ulster and Salisbury Turnpike" or just the "Salisbury Turnpike". The turnpike crossed the
Hudson River
The Hudson River is a river that flows from north to south primarily through eastern New York. It originates in the Adirondack Mountains of Upstate New York and flows southward through the Hudson Valley to the New York Harbor between N ...
from
Kingston to
Rhinecliff by way of the Kingston–Rhinecliff Ferry and used modern Rhinecliff Road and West Market Street to reach the
village of Rhinebeck. East of Rhinebeck, the turnpike passed through the
hamlet
''The Tragedy of Hamlet, Prince of Denmark'', often shortened to ''Hamlet'' (), is a tragedy written by William Shakespeare sometime between 1599 and 1601. It is Shakespeare's longest play, with 29,551 words. Set in Denmark, the play depicts ...
s of
Eighmyville,
Milan
Milan ( , , Lombard: ; it, Milano ) is a city in northern Italy, capital of Lombardy, and the second-most populous city proper in Italy after Rome. The city proper has a population of about 1.4 million, while its metropolitan city h ...
, Lafayetteville, and
Pine Plains and the village of
Millerton on its way to the Connecticut border. The turnpike corporation operated through the late 19th century.
In the mid-1920s, the portion of the Ulster and Delaware Turnpike from Lafayetteville to modern
NY 22
New York State Route 22 (NY 22) is a north–south state highway that parallels the eastern border of the U.S. state of New York, from the outskirts of New York City to the hamlet of Mooers (CDP), New York, Mooers in Clinton County, ...
in
North East was designated as part of NY 41, a new route extending from
Barrytown, a riverside hamlet north of Rhinecliff, to North East by way of
Red Hook, Lafayetteville, and Pine Plains. The designation lasted for only half a decade as NY 41 was renumbered to NY 199 as part of the
1930 renumbering of state highways in New York.
Kingston–Rhinecliff Bridge
Initial plans for the
Kingston–Rhinecliff Bridge, a structure that replaced the ferry between the two locations, called for the bridge to span the Hudson River between downtown Kingston (at Kingston Point) and the village of
Rhinebeck along a corridor similar to that of then-
NY 308. Due to political and economic factors, the bridge site was moved upstream (northward). The partially completed bridge opened to traffic on February 2, 1957, as a realignment and extension of NY 199. The route left its original alignment east of Barrytown and followed
NY 9G southward to the eastern bridge approach in the
town of Rhinebeck. From there, NY 199 crossed the new bridge and ended at a junction with
NY 32 just west of the Hudson River, then the western endpoint of the Kingston bridge approach. An extension of NY 199 west to
US 9W
U.S. Route 9W (US 9W) is a north–south U.S. Highway in the states of New Jersey and New York. It begins in Fort Lee, New Jersey, as Fletcher Avenue crosses the US 1–9, US 46, and the Interstate 95 (I-95) approac ...
was completed in the late 1950s; in 1964 the completion of the Catskill Expressway portion of U.S. Route 209 allowed more direct access from Route 199 and the bridge to the
New York State Thruway
{{Infobox road
, state = NY
, type = NYST
, alternate_name = Governor Thomas E. Dewey Thruway
, maint = NYSTA
, map = {{maplink, frame=yes, plain=yes, frame-align=center, frame-width=290, type=line, stroke-width=2, type2=line, from2=New Yor ...
.
The original routing of NY 199 from the Hudson River at Barrytown to NY 9G remained state-maintained as a
reference route for just over two decades. On April 1, 1980, ownership and maintenance of the highway, named Barrytown Road, was transferred from the state of
New York to
Dutchess County as part of a highway maintenance swap between the two levels of government.
Barrytown Road is now designated as CR 82.
Major intersections
See also
*
List of county routes in Dutchess County, New York
*
New York State Bicycle Route 199
References
External links
{{NYSR external links, type=N, nyroutes=yes, termini=yes, route=199, alps=yes, unyrds=us209-ny199
Kingston–Rhinecliff Bridge @ NYCROADS.comUnbuilt Catskill Expressway @ NYCROADS.com
199
Transportation in Ulster County, New York
Transportation in Dutchess County, New York
Limited-access roads in New York (state)