I wish I had access to my parents old pictures right now, but they're 900 miles away. @CrealCritter, like stated by NHH, I think the old loggers poles looked just like that, used in upper Michigan and Wisconsin. My mom's grandfather was a logger, and my dad's uncle's ran the logging camps. We've got tons of great old pictures, I just don't have them here.
No idea....my first guess would be a board road like the oil field workers use to be able to drive across fields without getting bogged down in the mud - but somehow I don't think it's a mud-related issue there.