Last fall was about as ideal as it gets, IMO. September torch and the first half of October was a torch through 10/12... including days of +19, +22, and +17 departures.
But then the switch was flipped as 16 of the last 19 days of last October were below normal (to much below normal) with several days of snow in the air (and even accumulations down here in the valley). That continued with record mountain snows in November (deepest Mansfield depth ever recorded in November) and steady snow cover beginning November 12th in the valley.
But to your point, going torch until mid-October is great for outdoor recreation, but then rip the band aid off and go straight to snow temps the second half of October. We went from highs around 80F on October 10th, to highs in the 30s on the 18th. One week is all it took to go from summer to snow last year.