u/swazal

This caught my attention, thinking it was a typo.

"Good evening. Mr. Baggins! [the Gaffer] said. "Glad indeed I am to see you safe back. But I've a bone to pick with you, in a manner o' speaking, if I may make so bold. You didn't never ought to have a' sold Bag End, as I always said. That's what started all the mischief. And while you've been *trapessing* in foreign parts, chasing Black Men up mountains from what my Sam says, though what for he don't make clear, they've been and dug up Bagshot Row and ruined my taters!” (emphasis added)

The word trapessing appears to be linked to *traipse*, a slang word from the 16th century meaning something like wander aimlessly on a journey, later *trapes* to describe more unsavory characters in the 17th century and into the 18th, with Pope and Swift using it as a derogatory term. Pretty sure the Gaffer wasn’t being offensive!

There's a synophonic relationship between the term traipse and trespass, even though the words do not appear to be directly related. Trespass canonically was a transgression or act against God or church law in the 13th century. The Lord's Prayer conveys this more ancient meaning:

And forgive us our trespasses,  
as we forgive those who trespass against us.

Private property as a legal concept certainly exists in the Shire, with Bilbo’s household auction (presumed dead?) serving as one example and his will leaving Bag End to Frodo as another. Several mentions of trespassing occur in Shire action in particular because private property is both a physical and a legal construct of hobbit society.

“What’s wrong with old Maggot?” asked Pippin. “He’s a good friend to all the Brandybucks. Of course he’s a terror to trespassers, and keeps ferocious dogs — but after all, folk down here are near the border and have to be more on their guard…. Old Maggot is really a stout fellow — if you leave his mushrooms alone. Let’s get into the lane and then we shan’t be trespassing.”

“No, I caught ‘em trespassing,” said the farmer, “and nearly set my dogs on ‘em; but they’ll tell you all the story, I’ve no doubt.”

Strider had changed his mind, and he decided to leave Bree by the main road. Any attempt to set off across country at once would only make matters worse: half the inhabitants would follow them, to see what they were up to, and to prevent them from trespassing.

"What's all this?" said Frodo, feeling inclined to laugh.
"This is what it is, Mr. Baggins," said the leader of the Shirriffs, a two-feather hobbit: "You're arrested for Gate-breaking, and Tearing up of Rules, and Assaulting Gate-keepers, and Trespassing, and Sleeping in Shire-buildings without Leave, and Bribing Guards with Food."

Traipsing about would involve some aspects of trespass, so was the Gaffer’s trapessing actually his pronunciation of “trespassed” or traipsed?