This winter (2015-16) the first day to have a high of 32° or colder wasn't until Jan. 5, which is about three weeks behind schedule. It was the tenth winter of the past 100 years to have the first such day occur in January (and the previous winter's first freezing high was on Dec. 31). At the other end of the spectrum, the earliest date for the first 32° high temperature occurred in 1942 on Nov. 14. The last time New York City had a high this cold in November was just two winters ago, on Nov. 24, 2013. The chart below lists the ten winters that had their first 32° high in January:
It should be noted that a late start to the winter doesn't necessarily translate into a continued mild season. Although the winters of 1919, 1975, 1998, 2008, 2012 and 2016 were very mild (2016 and 2012 were the second and third mildest, and 1998 was fifth), four of the winters on the chart above had periods of frigid temperatures and snow:
Winter of 1987 - Two days after the winter's first high of 32° or colder (on 1/20), a snowstorm dumped 8.1" of snow, which was then followed by five days with highs below freezing. In the four weeks following the first high of 32°, temperatures were 2.5 degrees below average, and 14.4" of snow fell.
Winter of 1985 - In the four weeks that followed the first 32° high (on 1/9), temperatures were five degrees below average. A major Arctic outbreak produced one of New York's coldest days in recent memory, with a high/low of +9°/-2° on Jan. 21. And in the 3-week period between Jan. 17 and Feb. 6, there were three snowfalls between four and six inches.
Winter of 1972 - A few days after the first high of 32° (on 1/6) there was a streak of five days in which temperatures were 16 degrees above average. Then an Arctic outbreak moved in mid-January that dropped the temperature to +5° on Jan. 16. February was cold and snowy, with eighteen inches of snowfall. Between Feb. 5 and 23 temperatures were four degrees below average and, similar to the winter of 1985, there were three snowfalls between four and six inches.
Winter of 1924 - Although January had average temperatures, there were four mornings with lows in the single digits (two lows of 5°, and two of 7°). February was cold (five degrees below average) and 8.5" of snow fell on April 1.