How place do you want to hike in Japan?

I'm Japanese and making a plan about "Hiking in Japanese old towns" in Nagano.
Then, I want to ask you 3 questions.

1.If you go on a hike in japan, How place do you want to do that?

2. Do you know following places?
・Magome-juku
・Tsumago-juku
・Narai-juku

3.If you go to Nagano to drink, how long do you want to stay? 3 days or 7 days or more?

I'm looking forward to getting answer!

Thanks

1. Assuming you mean "where" (どこ) or "what sort of place" (どのような場所) and not "how", I choose hikes based on the scenery. For example, we hiked to Motomachi on Rebun-tou for the views. It was worth it too!

2. I've heard of all of them and will be visiting Magome and Tsumago this winter, however we won't be hiking because of the snow.

3. I'd stay in Nagano city 3 days if it weren't winter. Some attractions are closed then.

1) Depends on time available. Most of the time, I only have a day or two so I go with shorter hikes. This includes something like hiking down the Kiyotaki from the Takao Temples to the Hozugawa in Kyoto, Magome to Tsumago on the Nakasendo, or short hikes in places like Kirishima or Aso National Parks (i.e. climbing Takachiho-no-mine).

If I have a few days, I can do an overnight, such as climbing Miyanoura-dake in Yakushima.

2) Yes. The walk between Magome and Tsumago was more interesting than the towns themselves. Especially Tsumago which was filled with tourists and shops containing nothing but souvenirs. Narai-juku was a bit more interesting in that it is still a town that people live along the main street. There were ticks (dani) on the trail up to the pass the last time I was there though. Also, the walk between Kiso-HIrosawa and Narai is short and easy. Hirosawa is a noted lacquerware town if you want to see some crafts.

3) Why would I want to go to Nagano just to drink? In Japan, there is no shortage of places to drink anywhere. If traveling through an area that's famous for some drink, I'll sometimes seek it out, such as at an izakaya in Niigata or Kitakata to try some local nihonshu.

(1) Kumanokodo.
(2) No, no, no.
(3) 0.

(1) Is you want to hike in Japan, what are you looking for?

I look for a simple hike that has easy transport links (2-6 hours) and is not too busy. It should also be well signed - at least in Japanese but hopefully in English.

(2) Have I heard of Tsumago, Magome and Narai?

Yes - this is along the Nakasendo trail. I have not visited Narai though.

(3) If I visit Nagano, how long will I spend there?

Are you talking about the city or prefecture? I would only spend 1/2 nights in the city (there is not too much to do) but could easily spend a week in Nagano prefecture. It's easy to complete a day trip to Yamanouchi, Togakushi Shrine or Obuse from Nagano City.