I researched the information about the dates in Annie Warbucks myself, using the dates indicated in the Playbill as my first clues and then using what is said in the script. I published my findings in our newsletter, Annie People, in the January 1996 issue, #76.
Note: Back in 1934, New York's weather readings were taken at Battery Park. They were also taken at Central Park, but the Battery ones were the official ones. Around 1961 the city decided to use the Central Park readings as the official ones. That is why if you look it up today, the record low for New York is 15 below, because that's what it was at Central Park the same day the Battery showed 14 below. But the Warbucks Mansion was closer to Central Park than the Battery anyway.
Here is my article that I did in early 1996:
THE COLD RAIN IN ANNIE WARBUCKS
Trying to speculate on the "exact" dates, as far as I could determine, of the chronology of events in Annie Warbucks proved to be an interesting task, and by the time I had finished, I'd discovered something rather interesting about the Warbucks Mansion at 987 Fifth Avenue in New York.
Obviously, the first scene of AW begins on Monday, December 25, 1933, since it is Christmas Day. The date of the next scene is unable to be determined from there, so instead I worked on Act II first. The script says that the scene with Annie at the Pattersons' was on a Monday in early April 1934. Let us assume that it is the first Monday in the month, April 2. In Tennessee it very likely would be warm enough in early April for C.G. to be barefoot outside. The next day, April 3, was the White House scene, and the party on the Staten Island Ferry was the following Saturday, or April 7. The script states the party was on a "balmy" Saturday evening. According to New York weather statistics at Battery Park (back then the readings were taken there; now they are taken at Central Park and the airports), the high temperature for April 7 was 49 degrees; that up front doesn't sound too balmy, but when we realize that 1933-1934 was overall the coldest winter in New York City history with rare below zero readings occurring several times, we can suppose that 49 must have felt "balmy" to New Yorkers. (If they had held the party two days later on April 9, it would have been 68 degrees!) The show concludes on Wednesday, April 11, 1934 with the wedding at the Waldorf (a nice 53 that day).
Let us now work backward from the first scene in the second act, April 2. The script states that this is 6 weeks after the previous scene, which took place on a Thursday. Counting back 6 weeks from April 2 and then back to the previous Thursday, we find that the scene where Oliver Warbucks is meeting Commissioner Doyle at her office to sign the papers is Thursday, February 15. Since this scene was "the following Thursday," the most logical date on which the previous scene could have happened was Friday, February 9. This was when Drake and the Servants sing "That's The Kind Of Woman" and Warbucks sings "A Younger Man." Before the songs are sung, Commissioner Doyle is at the Mansion suggesting some more women for Warbucks to go out with, and as she is leaving, she reminds Warbucks that there are "34 days" left before the deadline for his marriage is up. It is here we run into a slight problem with the dates: That would make February 9 the 26th day since the 60 days began, making it so that the 60 days did not officially begin until Monday, January 15. In order to make the stated April date at the beginning of Act II fit, we have to assume that the Commissioner took three weeks after Christmas to draw up the necessary papers (which Warbucks did not sign until February 15 anyway). Of course, the 60th day, whenever it was, turned out to be irrelevant, since the whole thing was put on hold while Annie was missing, and she wasn't reunited with "Daddy" Warbucks until Tuesday, April 13.
The Orphanage scene, which happened "a month" before February 9, took place on or about January 9. Since it took place on a "chilly, wintry day," the 9th would be possible, since the low temperature that day was 36 degrees, and as any New Yorker knows, with the wind whipping around the buildings, it could feel a lot colder than 36. January 10 had a low of 32 and January 11 had one of 29, making them also possible dates for this scene. Of course, since Warbucks was about to take Mrs. Whittleby to lunch, the temperature might have been a little higher by that time in the day but still plenty wintry.
Incidentally, Annie's first week at the Mansion was interesting, weatherwise. 1933 had a rather warm Christmas that year, topping out at 54 degrees. Five days later, on December 30, a very sudden and severe cold wave dropped New Yorkers down to 6 below zero, one of the (20th) century's coldest readings. But then the next day, December 31, it was back up to 42 degrees.
The most interesting scene though, as relates to the chronology of Annie Warbucks, was the day at the Mansion when Commissioner Doyle was talking about additional eligible women for Warbucks to date. Mrs. Kelly arrived, bringing some more files up from the office, and the Commissioner told her to take a bus back or walk, but Warbucks took pity on her and gave her a dollar for a taxi. From Mrs. Kelly's point of view, it was very generous of Warbucks to make that offer, because, as we have deduced above, this scene took place on the 9th of February. There was no way Warbucks was going to allow the Commissioner to make a human being walk through New York or stand at a bus stop on that particular day! For, you see, this was no ordinary day.
It happened that Friday, February 9, 1934 was the coldest day ever recorded in New York City, with the temperature getting down to an astonishing 14 degrees below zero at 7:15 that morning at Battery Park! No day since then has even begun to approach that incredible record low in New York which very likely will never be broken. Even during the day of February 9 the mercury climbed up to only 8 above, which means in the morning when this scene was taking place, the temperature was very likely still way below the zero mark.
But wait! Warbucks told Mrs. Kelly he was going to give her a dollar because it was "pouring" rain. Rain? On the coldest day of all-time?? Hmmm.... To record a low temperature record of such magnitude, there couldn't have been a cloud within miles of New York. But who knows? Maybe it was raining ONLY around good o1' 987 Fifth Avenue but nowhere else in the city! The script does say the scene took place on a "rainy winter's morning in February." In any event, next time you watch that scene in Annie Warbucks, be happy for Annie and Sandy and "Daddy" and everyone else who was inside, because outside it must have been a very cold rain....