New York State Route 311

Part of modern-day NY 311 from the NY 292 intersection to the route's ending terminus was once part of the Philipstown Turnpike. Initially, the county's proximity to the Hudson River supplied cheap means of transporting goods to Albany and New York City, though in the winter months, the river froze over.[9] To resolve the issue, in 1815, the Philipstown Turnpike Company was organized to improve upon a toll road from Cold Spring to the Connecticut border.[10] On April 15, 1815, "an act to incorporate the Philipstown turnpike company in the county of Putnam" was passed.[11] East of the Connecticut border, the turnpike continued as the New Milford and Sherman Turnpike.[12] On the turnpike, wagons transported manufactures inland, and carried produce from the eastern part of the county.[9] Before the advent of the railroad, the road was a business center for much of the county.[13] One of the intentions of the turnpike was to "greatly promote the public good, as well contribute to their individual interest". However, the turnpike proved unprofitable[9] and was eventually abandoned.[12]

Looking east on NY 311 in Patterson

In November 1901, the Putnam County's Board of Supervisors hired an engineer to create plans for a new road that would run from the Westchester–Putnam County border into Dutchess County. By early the next year, a group of engineers led by H. W. Degaff surveyed the region, with the goal of constructing a 16-foot (4.9 m) wide road. In October 1902, the Board of Supervisors was informed that the engineers planned to build the new road along a path similar to an existing road. Surveys were completed in 1907, resulting in the elimination of a dangerous railroad crossing via a trestle. Actual construction began on the Patterson portion of the state road in April 1909, beginning from the Patterson Baptist Church near the modern-day intersection of NY 311 and NY 164. The working crew was composed of Italian immigrants, some of whom were given temporary residence within the Putnam Cigar Factory. By June, construction had reached the Village of Patterson, completing the project.[14]

The portion of modern NY 311 from NY 292 in West Patterson and NY 22 in Patterson was designated in the mid-1920s as part of NY 39, an east–west route extending from Poughkeepsie to Patterson via East Fishkill and West Pawling.[15][16] In the 1930 renumbering of state highways in New York, the segment of NY 39 east of West Patterson was renumbered to NY 311 while the portion of 1920s NY 39 from East Fishkill to West Patterson became part of NY 52. NY 52 also continued south from West Patterson through what is now Lake Carmel to Carmel, where it continued east on an overlap with U.S. Route 6 (US 6).[2][17]

In March 1936, a "great and unusual ice flood" caused local water levels to rise.[12] The bridge carrying the highway over the Great Swamp received cracks in its foundation due to the pressure of the water and melting ice, and was lifted off its foundation and swept into the swamp.[14] NY 52 was realigned c. 1937 to follow its current alignment between Stormville and Lake Carmel. The former routing of NY 52 from West Patterson to Lake Carmel became part of an extended NY 311.[18][19]

The NY 311 Harlem Line railroad crossing

In June 1960, the Presbyterian Men's Club produced a film called Our Town, part of which was filmed on the Main Street portion of NY 311 at Boot Hill, a replica western frontier town. Children were asked to participate in the filming by dressing in western or American Indian apparel; girls dressed as frontier women. The film debuted at the Patterson Town Hall on September 24, 1960.[20]

By 1966, Putnam County's men began drafting into the armed forces to fight in the Vietnam War. In November of that year, Local Board No. 14 announced that 21 local men would be drafted into the military, the highest total to be called since the Korean War. Of the 21, two were residents of Patterson.[20] To honor the Patterson veterans who lost their lives, a plaque commemorating the Vietnam War was added to the War Memorial by the American Legion at the intersection of NY 311 and Maple Avenue.[21]

The Patterson Post Office underwent several re-locations throughout the years. After the Lloyd Lumber Company moved to a larger building along NY 311, the post office occupied the smaller structure; both were situated on the east side of the New York Central tracks. Residents complained that the new location was inadequate, claiming that parking was insufficient at nearby companies, and that walking along a busy road to reach the post office was dangerous. After a bidding process to determine the future location, the office was again moved to a former car service station along Front Street.[22]