Last November, my friends and I planned a 'do-it-yourself' hike in Nakasonde. It was fairly easy from Nagiso to Tsumago and then to Magome where we stayed. There were well marked trail signs in English every kilometer or so. Note that the locals do not speak English and the signs helped us a lot to get around.
However, from Magome to Nakatsugawa it was totally different. The trail signs were all in Japanese. We were lucky that one of our hiking buddies could read Hanzi (Chinese) which is basically Kanji (Japanese) and could make out the characters to Nakatsugawa.
Despite though this lost in translation situation where we ended up knocking on someone's home for help (the Japanese are truly helpful and kind), the hike was absolutely beautiful and worth doing. The trail offered several attractions - waterfalls, gorges, temples, farmlands but the best was the beautiful scenery with the changing of leaves. We were surrounded by red, orange, gold, pink leaves - an explosion of colors.
Note that I agree with Bakatori to check the train schedule of your next stop. There's not much to do in Nakatsugawa. I'm glad that we made it on time to catch our train to Kyoto where there's more to see and do. Also, to book your accommodations at least 3-4 months in advance.
If I am going to hike Nakasendo again, I'd stay for 4-5 days and hike all the way to Kyoto.
Sharing my Nakasendo experience: http://www.rosancruz.com/2013/11/nakasendo-hike-from-tsumago-to-magome.html
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