The Autumn season is best known in Japan for Koyo, which essentially means "trees changing colour". Most areas in Japan during the months of October, November, and December transform themselves from hot humid places into dry beautiful picturesque landscapes.
Last year I went to two areas that I highly recommend: Myoko Kogen in Niigata, and Shiga Kogen in Nagano.Getting there by car is the easiest way to take advantage of the beautiful mountains, as there aren't really any trains and buses are limited at best.
From Tokyo: Take the Kan-etsu Expressway towards Niigata, followed by the Joshin-etsu Expressway which leads towards Nagano. The Myokokogen Exit is the one you are looking for.
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The other area is called Shiga-Kogen, which lies on the border between Nagano and Gunma Prefectures. Its a really nice long drive in the mountains if you want to make your way slowly back to Tokyo. Here is my recommended route:
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From the Shinshu-Nakano IC, you can make your way up into the mountains and drive on the highest road in Japan on 292. Following this, you can make your way down the mountain into Gunma and eventually the Takasaki IC which will take you back to Tokyo directly.
Here's an example of what's waiting for you:

Happy Travels!
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