Doesn't that depend a bit on the engine driving the chainring.
As well as the cassette in the rear.
And the hills you're climbing.

Perhaps also whether you are able to take a rest break when needed. I've encountered hills that went along fine most of the way up, then got steap near the peak. But, stopping once or twice, and one can make it up... then off for the rest of the ride.

Stuff like raingear depends on where you're travelling. Here on the west coast, I wouldn't anticipate significant rain for another month or so. Perhaps bring the thinnest, lightest raingear needed. Even in the midwest, rain storms often hit with a bang, then are over in a few minutes.