I am a chief editor, and to accomplish some missions, I am recently visiting often to Nagano every month.
It is very cold here, compared to Tokyo, in this season, so I cannot leave without the extreme warm heat-tech. I would like to introduce the recommended zekkei (great view) spots in Nagano over two issues for this time!
I will present you the sightseeing spots of particularly "easy to tour around by trains", which is unique to the chief editor who is an inexperienced driver.
I will add information for the recommended guest house. Now, the first issue is around Matsumoto.

It takes about 2 hours and 30 minutes from Shinjuku to Matsumoto station by Chuo line "Limited express Azusa". Having souvenir shops and restaurants spotted around, with some fashionable cafes recently opened, the Matsumoto station is a recommended spot, for just going-out-of-town type trip.

Matsumoto castle is beautiful, particularly with its reflection on the glassy surface of the water. There were many people taking pictures around the moat.

You can tour inside of this castle. Paid admission, and toured with climbing up on narrow stairs. I had to take off my shoes to enter, and please be very careful because "the wooden floors were icy-like extreme cold" in the winter season..... Please block the cold by wearing thick socks by all means. You can view such landscape from the top. Let's tour with thinking far away of people lived in this castle.

About 10 minute walk from Matsumoto castle, I went to the Old Kaichi School, which is the oldest elementary school in Japan, constructed in early Meiji era.

Unfortunately, exterior walls were under construction.

You can observe the school of the past. Feel something thrilled, don't we? Please be careful also here because under foot is very cold.

Small and cute are desks and chairs. You can learn by reading some compositions written by children of a past.

Details Here: https://www.city.matsumoto.nagano.jp/sisetu/marugotohaku/gakko/

It is said that Yayoi Kusama, who is famous for sculptures of polka-dot patterns and paintings is from Matsumoto city. There were a large monument in the art museum, also were permanent exhibition. Unfortunately, when I visited, I could not see it in relation of special exhibition. Please be careful if you desire to see the works by Yayoi Kusama.

A very cute art work will welcome you.

Surprisingly, in the last exhibit room I was allowed to take pictures. It is a good service that you can post them also on SNS!

At the last, I thought to buy a Kusama dot-cola that I was expected (on the upper row), but it was not for sale...... The art museum is also walk-able distance (about 12 minutes) from Matsumoto station.
Details Here: http://matsumoto-artmuse.jp/

There are many houses of Dozou Zukuri (built like a kura, with the walls covered in mud) in such white and black colors in Nakamachi street.

It is elegant. The shops lined up are many fashionable shops.
Details Here: http://youkoso.city.matsumoto.nagano.jp/wordpress_index-p_182-htm

"Temariya", a baumkuchen shop in Nakamachi street, is recommended. It is a baumkuchen that is made of rice powder of Koshihikari (a variety of rice), a product of Azumino, and a-whole-rice powder. Sweets friendly to you body, that are made of carefully selected ingredients of Nagano, are perfect fit to souvenir.
Details Here: http://www.temariya.jp/