I decided to check Elwyn's diary to see what the weather was like in other years. I checked 19 years from 1917 to 1975. The two most common types of weather were "generally bright and sunny. Clear still frosty evng. Typical colorful tingy autumn weather" (1959) or "a rough day, strong south westerly winds, mostly cloudy, rain squally evng" (1934).
It was not uncommon to have the first killing frost, the first flurries, or the first snowfall on the mountains. "Rained hard during night & rained this forenoon. Snow squalls on mountains. Tops of mountains white – colder" (1920). Occasionally it was really warm. In 1946, it was "brisk southerly winds. Partly cloudy Starlight evng. Real summery weather - Katydids chirping." In 1938, it was "continued warm shirt sleeve weather. New York City temperature 10 above normal." In 1936, that week was record-breaking cold: it was "coldest Oct 27 New York City ever recorded."
Sometimes something else jumps out, nothing to do with weather. It seemed to be a day he often went to the movies. On October 29, 1951, he "saw a most interesting patriotic film in color and musical feature Wait Till The Clouds Roll By." In 1947, he "went to Phoenicia evng - Interesting picture program feature film Treasure Island in cinecolor." And on October 29, 1940, "the nations first peace time national draft lottery opened at noon in Washington. First number drawn was 158, 2nd 192, 3rd 8239, 4th 6620."