Tokyo to Kusatsu onsen town timetable

Hi, I have planned a trip to Kusatsu onsen town from Tokyo on 31/10/18 & will leave on 1/11/18.
We are only there for one night & would like to make the most of it.

I am interested in the Shinkansen option that I saw form a previous post (the fastest route)
> Tokyo or Ueno -(JR Shinkansen)- Takasaki -(JR Joetsu Line (until Shibukawa) + JR Agatsuma Line)- Naganoharakusatsuguchi -(JR Bus Kanto)- Kusatsu Onsen.

However, from your page https://www.japan-guide.com/e/e7403.html it states that there are three round trips. I was wondering if you knew the times for these trips?

I arrive in Tokyo in the evening of 30/10/18, would I be able to organise tickets that evening or even prior?

Kindest regards

The three round-trip per day refer to direct trains between Ueno and Naganohara-Kusatsuguchi; that's not what you plan to do.

If you are interested, however, you have two departures from Ueno on 31/10, at 10:00 and 12:12, and from Naganohara-Kusatsuguchi on 1/11 at 13:07 and 15:43. You can see Hyperdia for details.

If I'm guessing correctly, using the Shinkansen, you have to do a extra transfer.

TBH, I would skip the place and choose somewhere else, if you arrive in Tokyo in the afternoon, it will take about 3 hrs to get there, you don't have much time there.

OP arrives in Tokyo in the evening of the 30th. It would probably make more sense to take an earlier train on the 31st, even though it won't be direct.