Tokyo to Nagano walking as much as possible?

I plan to travel from Tokyo to Nagano district in November this year and have decided to hike as much of it as possible. I know its a fair distance so would like to combine walking trails/pilgrimage routes with public transport.

Does anyone know the feasibility of this idea and have any tips about what areas are best to hike and how popular this is. Im young and fit so ability is no problem its more accommodation, correct routes to take and where is the safest or most beautiful to take on foot. I have heard the Japanese are very accommodating to visitors and pilgrims along many of the ancient walking routes out of Tokyo so anyone with information or links to help out would be appreciated. Just starting to plan so at the moment anything I hear will be of help!

Cheers

Ross

Perhaps this as a guide.

http://www.japanpackage.com.au/package34.htm

Tokyo to about mid-Saitama on your way to Nagano is not going to be pleasant. You'll be walking on concrete sidewalks to cityscape smelling the nice smell of exhaust the entire way. I'm sure there are smaller roads that will get you off the main areas, but that seems like a waste of time. Take public transportation to a point outside Tokyo to begin your walk if you're wanting nature.

Not recommend any seasons by walk all.
BC some roads and tunnels not for walker/biker(cyclist) no escape space enough very dangerous.
Some part(tunnels and over pass of montain area) by hitchhiking easier,safe and faster.

This is drive recorder vids of "National route 20[国道20号]"
from mid Tokyo Nihonbashi[日本橋] to Shiojiri[塩尻] in Nagano PF[長野県].
(not Nagano city[長野市])
https://www.youtube.com/playlist?list=PL8G2-9LZ-ouHIBssknWMbsi1yb0UtiP...
http://en.wikipedia.org/wiki/Japan_National_Route_20
This is Sasago tunnel about 3000m long by regular car and bus.
http://youtu.be/KkjaNh9DvTM
http://youtu.be/Sq2UI_82Hcg

I definitely recommend walking! I'm not sure where in Nagano you want to go, but to get to Lake Suwa, for example, you could follow either the old Nakasendo through Kumagaya and Takasaki and over the Torii Pass to Karuizawa and then on to Saku and Lake Suwa, or the old Koshu Kaido through Hachioji, Otsuki and Kofu to Lake Suwa. Both routes involve lots of walking alongside roads, but no tunnels. Instead you go over passes (Usui Pass and Wada Pass on the Nakasendo, Kobotoke Pass and Sasago Pass on the Koshu Kaido).

I have walked both of these routes, though in the reverse order (towards Tokyo). You can read about my experiences here:

Nakasendo:
http://thewalkingfool.blogspot.co.nz/search/label/The%20Nakasendo%20di...

Koshu Kaido:
http://thewalkingfool.blogspot.co.nz/search/label/The%20Koshu%20Kaido%...

PS As you will see from my diaries, I walked the stretch of the Nakasendo between Lake Suwa and Tokyo in early to mid November. It was pretty cold around Karuizawa at night, but there was no snow on the roads anywhere. Later in November might be a different story.