Massachusetts Route 295
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Map of Columbia County in eastern New York with NY 295 highlighted in solid red and of western Massachusetts with MA 295 highlighted in dotted red
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| Maintained by NYSDOT and MassDOT | ||||||||||
| Length: | 14.568 mi (23.445 km) 12.88 mi (20.73 km) in New York 1.668 mi (2.684 km) in Massachusetts |
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| Existed: | c. 1931 – present | |||||||||
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| West end: |
 NY 66 in Chatham, NY
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| East end: |
 Route 41 in Richmond, MA
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| Counties: | Columbia (NY), Berkshire (MA) | |||||||||
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New York State Route 295 (NY 295) is a 12.88-mile (20.73 km) state highway in Columbia County, New York, in the United States. It begins at an intersection with NY 66 in the village of Chatham and heads generally easterly to the Massachusetts border in the town of Canaan, where the road becomes Massachusetts Route 295 for another 1.668 miles (2.684 km) to a junction with Route 41 in Richmond, Massachusetts. Route 295 is the highest numbered Massachusetts state highway.
At its western terminus, NY 295 begins at NY 66 in the village of Chatham, initially known as Railroad Avenue. As the road changes names to Spring Street, the Stony Kill approaches from the west and roughly parallels NY 295 for much of its duration. Within the hamlet, NY 295 intersects several local roads and a pair of train tracks. The highway proceeds towards the northwest as it passes to the east of a pond, and subsequently intersects the Taconic State Parkway. Upon crossing the state parkway, NY 295 takes a more easterly direction; however, it turns towards the northwest when it reaches New Concord Road. The road intersects the Berkshire Connector of the New York State Thruway, or Interstate 90 (I-90), and enters the hamlet of East Chatham.
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