sequence of tenses:
- He had been a nice man until he became poor.
had been precedes became poor. Please see below.
"we have had to blaze a trail" would refer to the present:
We have had to blaze a trail to get here.
In your sentence, anything that precedes "was an old, old trail" occurred before the point in time when the trail became old. The trail had to be blazed before it could become old. It became an old trail after it was blazed. Everything is in the past.
Imagine a line with:L before some past | some past | present |future.
the old trail is past and the had had to blaze comes before it.