If the landowner is the Duke of Devonshire, and the land you want to walk on is the Derbyshire peak district, are you supposed to drive the 300 miles to ask?
As Woody Guthrie once sang; “this land is your land, this land is my land”. Which country was he from again?
Anyway, this is folly to hypothesise about because there are now well established rights of way and public footpaths (what you might call trails) criss-crossing the land, and have been for 60 years.
Woodie Guthrie was a flea-bitten hippie. I could not care less about his socialistic view of preperty rights. It doesn't comport with any laws over here, anyway. Most jurisdictions take a dim view of trespassing, and rights of way disputes require the courts. You can't just claim that you have a right of way that you've used for so-an-so number of years; you have to prove it. The landowner is permitted to rebut your claim, and in most states all he has to do is note the display of a "no trespassing" sign to win.