Map of the Mid-Hudson Valley with NY 199 highlighted in red | ||||
| Route information | ||||
| Maintained byNYSDOT andNYSBA | ||||
| Length | 30.91 mi[1] (49.74 km) | |||
| Existed | 1930[2]–present | |||
| Major junctions | ||||
| West end | ||||
| Major intersections |
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| East end | ||||
| Location | ||||
| Country | United States | |||
| State | New York | |||
| Counties | Ulster,Dutchess | |||
| Highway system | ||||
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New York State Route 199 (NY 199) is a 30.91-mile-long (49.74 km)state highway located in theHudson Valley of the U.S. state ofNew York. Its western end is inUlster County, where it begins as the continuation of the shortU.S. Route 209 freeway east of its interchange withU.S. Route 9W; after crossing theKingston–Rhinecliff Bridge over theHudson River the rest of the highway crosses northernDutchess County. As it does it passes through downtownRed Hook andPine Plains, reaching its eastern end atU.S. Route 44 andState Route 22 southwest ofMillerton 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, a toll road linkingBainbridge toSalisbury, Connecticut. This segment of the turnpike was incorporated intoNew York State Route 41, a new route connectingBarrytown to Millerton, in the mid-1920s. NY 41 was renumbered to 199 as part of the1930 renumbering of state highways in New York.
When the Kingston–Rhinecliff Bridge opened in 1957, NY 199 was realigned to continue across the bridge to the town of Ulster. The former routing of the highway between Barrytown andNY 9G along Barrytown Road remained state maintained until 1980, when ownership and maintenance of the highway was transferred toDutchess County. It is now designated asCounty Route 82 (CR 82).

The western terminus of Route 199 is the northern terminus ofU.S. Route 209 inUlster County. When the four-lanefreeway section of the latter road reaches thecloverleaf interchange withUS 9W, in the town ofUlster, betweenKingston andLake Katrine, it assumes the 199 designation as it continues eastward through woodlands. Veering slightly northward, it has another interchange withState Route 32 after a mile (1.6 km), with the eastbound lanes reaching the toll gantry for theKingston–Rhinecliff Bridge 0.4 miles (640 m) further on.[3]
West of the toll gantry, the highway becomes atwo-lane freeway before crossing the 1.5-mile (2.4 km) bridge, on an east-southeast heading. On the east bank, now in theDutchess County town ofRhinebeck, it remains two lanes as it traverses wooded areas, part of theHudson River Historic District, aNational Historic Landmark. The road returns to a due-east course shortly after the crossing; it becomes atwo-laneexpressway and has its first traffic light at the intersection with River Road (alsoCounty Route 103).[4]
At 0.6 miles (0.97 km) past that intersection, the highway reaches another traffic light atState Route 9G. It joins that highway northbound, immediately entering the town ofRed Hook, for a two-mile (3.2 km) stretch through woodlands, first heading northwest then due north.[4] The two lanes widen to four on either side of theRokeby Road intersection.[5]

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 thevillage ofRed Hook. At the village line, a mile east of NY 9G, it passes Red Hook High School, the historicMaizefield estate, and the middle school, becoming West Market Street. At the center of town, another traffic light marks the intersection withU.S. Route 9.[6]
NY 199 becomes East Market Street and leaves the village approximately a half-mile (800 m) to the east, curving gently through a mix of fields andwoodlots in the surrounding landscape. A mile (1.6 km) past the village, the road makes the first of four crossings of theSaw Kill. After crossing theLakes Kill a thousand feet (300 m) further on, the road starts a long turn southeastward past the formerSky Park Airport and Red Hook Golf Club.[7]
The Saw Kill crosses again just north of the end of this section, at the small hamlet ofRock City, where the towns of Red Hook, Rhinebeck andMilan 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.[8]
Past this point the highway bends southeast again, crossingLittle Wappingers Creek, as the landscape becomes hillier and more wooded. A mile and a half further it resumes heading east,[9] past Milan's town hall, to its interchange with theTaconic State Parkway,[10] climbing slightly.[9] East of the Taconic NY 199 crosses the small hamlet ofLafayetteville, turning to the north as it descends for a mile through a narrow, wooded valley to Wilbur Pond and Lafayetteville Multiple Use Area.[11]
For the next two miles NY 199 continues to descend, turning northeast and entering the town ofPine Plains midway. After crossingHam Brook, the highway turns north northeast for three-quarters of a mile (1.1 km), bending back to the southeast around the side of an unnamed hill.[12] 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 centralPine Plains,[13] where NY 199 passes Stissing Mountain High School and becomes West Church Street, still trending south.[14]

At the junction with Main Street in the center of town, the first traffic light since Rock City also marks whereState 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 theColumbia County hamlet ofAncram, ending the concurrency.[15]
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.[16] East of there, the road drops briefly into a swampy area, then climbs again as it turns southeast. At theNorth East town line, it reaches 1,000 feet (305 m) above sea level, the highest elevation along its route.[17] NY 199 continues southeast down a narrow valley for its last 2.3 miles (3.7 km) to its eastern terminus, atU.S. Route 44 andState Route 22 1.5 miles (2.4 km) southwest ofMillerton.[18]
On April 2, 1802, theNew York State Legislature created a turnpike corporation for the purpose of building a road—theUlster and Delaware Turnpike—from theSusquehanna River in the vicinity of the town of Jericho (nowBainbridge) to theConnecticut state line atSalisbury.[19] The portion of the Ulster and Delaware Turnpike east of theHudson River was also commonly known as the "Ulster and Salisbury Turnpike" or just the "Salisbury Turnpike". The turnpike crossed theHudson River fromKingston toRhinecliff by way of the Kingston–Rhinecliff Ferry and used modern Rhinecliff Road and West Market Street to reach thevillage of Rhinebeck. East of Rhinebeck, the turnpike passed through thehamlets ofEighmyville,Milan, Lafayetteville, andPine Plains and the village ofMillerton on its way to the Connecticut border.[20] The turnpike corporation operated through the late 19th century.[citation needed]
In the mid-1920s, the portion of the Ulster and Delaware Turnpike from Lafayetteville to modernNY 22 inNorth East was designated as part of NY 41, a new route extending fromBarrytown, a riverside hamlet 6 miles (10 km) north of Rhinecliff, to North East by way ofRed Hook, Lafayetteville, and Pine Plains.[21][22] The designation lasted for only half a decade as NY 41 was renumbered to NY 199 as part of the1930 renumbering of state highways in New York.[2]
Initial plans for theKingston–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 ofRhinebeck along a corridor similar to that of then-NY 308. Due to political and economic factors, the bridge site was moved 3 miles (5 km) upstream (northward).[23] The partially completed bridge opened to traffic on February 2, 1957,[24] as a realignment and extension of NY 199. The route left its original alignment east of Barrytown and followedNY 9G southward to the eastern bridge approach in thetown of Rhinebeck. From there, NY 199 crossed the new bridge and ended at a junction withNY 32 just west of the Hudson River, then the western endpoint of the Kingston bridge approach. An extension of NY 199 west toUS 9W was completed in the late 1950s;[25][26] 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 theNew York State Thruway.[27]
The original routing of NY 199 from the Hudson River at Barrytown to NY 9G remained state-maintained as areference route for just over two decades. On April 1, 1980, ownership and maintenance of the highway, named Barrytown Road, was transferred from the state ofNew York toDutchess County as part of a highway maintenance swap between the two levels of government.[28] Barrytown Road is now designated as CR 82.[29]
| County | Location | mi[1] | km | Destinations | Notes |
|---|---|---|---|---|---|
| Ulster | Ulster | 0.00 | 0.00 | Continuation south | |
| Cloverleaf interchange | |||||
| 0.98 | 1.58 | Parclo interchange; last eastbound exit before toll | |||
| Hudson River | 1.37– 3.00 | 2.20– 4.83 | Kingston–Rhinecliff Bridge (eastbound toll) | ||
| Dutchess | Town of Rhinebeck | 4.44 | 7.15 | Eastern end of limited-access section | |
| Western end of NY 9G concurrency | |||||
| Town of Red Hook | 6.39 | 10.28 | Eastern end of NY 9G concurrency | ||
| Village of Red Hook | 8.15 | 13.12 | |||
| Milan | 11.91 | 19.17 | Eastern terminus of NY 308;hamlet ofRock City | ||
| 15.63 | 25.15 | Parclo interchange; exit 67 on Taconic State Parkway; hamlet ofLafayetteville | |||
| Town of Pine Plains | 22.58 | 36.34 | Western end of NY 82 concurrency; hamlet ofPine Plains | ||
| 24.01 | 38.64 | Eastern end of NY 82 concurrency | |||
| North East | 30.91 | 49.74 | Eastern terminus | ||
1.000 mi = 1.609 km; 1.000 km = 0.621 mi
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