Advise on my route plan

Hi I'm planning for a trip to Japan in mid Nov. I wish to visit places like Kariuzawa, Matsumoto castle , jigokudani money Park, Tateyama Alpine route, kurobe gorge n Kawaguchi.

My plan is to travel
1) from Tokyo to kariuzawa with 2 nights stay.
2) from Kariuzawa to Nagano with 2 nights stay. Day trip to Matsumoto castle n the monkey park
3) from Nagano to Toyama with 2 nights stay. Day trip to kurobe gorge and Tateyama alpine route.
4) from Toyama to Kawaguchi. Two nights stay
5) from Kawaguchi back to Tokyo. Will be travelling to Hokkaido after one day in tokyo

Is it possible to do all the attractions with this route? And what type of rail pass will be best for it? Heard that it's better to make reservation for Kurobe gorge Railway as considered peak season cos of the autumn foliage.

Besides visiting the attractions, like to do some fruit picking if possible.

I would say a night in each is sufficient time so two nights each is surely enough time.

You have 9 days listed, and the JR Pass is good for either 7, 14, or 21 days. Suggesting which JR Pass will depend on what you are doing in Hokkaido. That said, there are several things that will not be covered with the JR Pass.

Actually, there are 11 days, if you consider the extra in Tokyo, and going the following day to Hokkaido. It is a very long distance be rail. Are you flying?

There is a JR line from Nagano to Mastumoto, so that is no problem.
There is a Bus, or, the Private rail to get to the Monkey Park:
http://www.japan-guide.com/e/e6027.html
Shiakawa-go is also by private transportation:
http://www.japan-guide.com/e/e5953.html
The Alpine route.... Well... You may be seeing a pattern here:
http://www.japan-guide.com/e/e7551.html
And the Kurobe Gorge:
http://www.japan-guide.com/e/e7575.html#/section_getThere

So... lots of the things that you are doing will cost for private transportation, and a JR Pass will not help. But, it will help for getting BETWEEN cities.

It depends on what you are doing in Hikkaido, and how much use the JR Pass is up there.

If you are willing to move things around a bit, I can suggest the Hokuriku Arch pass, and the Tokyo Wide Pass. This can be accomplished by moving Kariuzawa to the end of your journey.

Start by activating the Hokuriku Arch Pass on arrival:
http://www.japan-guide.com/e/e2361_arch.html
1) Tokyo to Nagano for 2 nights.
2) Nagano to Toyama for 2 nights.
3) Toyama to Kanazawa (rail) and then a bus to Shirakawa-go for 2 nights.
4) on the final day of the pass, go back to Kanazawa, and take the Shinkansen to Kariuzawa for 2 nights.

On the day you leave Kariuzawa, activate the Tokyo Wide Pass:
http://www.japan-guide.com/e/e2361_06.html
This is a three day pass.
Day 1: Kariuzawa to Tokyo
Day 2: transpotation around the Tokyo Area.
Day 3: Transportation from Tokyo to the Airport.

This may work for you. Good Luck with your planning.

Yes. I saw the Hokuriku Arch Pass. But I was wondering if I can get the flexible 5 days JR East Pass(Nagano,Niigata) which is much cheaper. For travelling in Tokyo, I don't mind paying for the fares instead of using JR Pass.

And I decided to move around my schedule by working anti clockwise instead and skip Tateyama alpine route
1. Lake Kawaguchiko 2 nights
2. Kurobe-Unazukionsen Station for Kurobe Gorge Railway 2 nights
3. Nagano 1 night
4. Karuizawa 2 nights
5. Back to Tokyo before heading to Hokkaido. Not planning to get any JR pass for Hokkaido

From Google, seem like I will make use of Hokuriku Shinkansen, Chuo Line Ltd Expess ( Azusua or Super Azusua) and Shonan-Shinjuku Line. Was wondering if this is covered by the Arch Pass or JR east pass. How about Shinonoi line & Fujikyuko Line to Otsuki Station, Matsumoto station n Nagano station?