General

Food

famous for soba, known as shinshu soba. The volcanic soil and extreme variance in temperatures within Nagano's highlands make it the ideal place for growing buckwheat in Japan.
famous for apples, try apple bread.
known for mushrooms
Oyaki - buckwheat dumplings street food stuffed with all kinds of stuff like collard greens, pumpkin, meat, sesame paste, azuki (similar to gyuman).

Gateway to the Japan alps.
Fantastic ryokan-like accomodation I stayed at.
Matsumoto Castle - A rare original castle (most others are modern reconstructions). An amazing lesson in old castle and weapon engineering.
- A great time to visit is in the spring when the grounds of the castle are powdered a soft pink with the bloom of thousands of cherry blossoms.
- Seeing the castle with the surrounding lake moat and the alps in the back was a lasting memory.
Ukiyo-e museum
Art museum - mostly houses works by Yayoi Kusama.
A vibrant cycling culture, Tour de Utsukushigahara cycling race.
Yamaya Candy Shop - currently run by the 13th generation family head Ota Yoshihi - learn to make their traditional rice candy.
Asama Onsen town ~20mins drive. Stay at the onsen book hotel Matsumoto Jujo where all rooms have their own private open air hotspring and beautiful reading rooms 📚
Utsukushigahara - another onsen town.