Tavern Puzzles get their name from their history of being available in Taverns to entertain and challenge their customers. In order to withstand lots if heavy use, they were made of forged iron by local blacksmiths. Also, they are much larger and heavier than conventional wire puzzles. Therefore, they can often be offered as smaller wire puzzles.
The Conestoga Playmate puzzle has been around for a long time and goes by various names and made by various companies and even by local puzzle makers.
Where the name Conestoga comes from, I don’t know; but an older name for it is the Gingerbread Man Puzzle. That name is obvious from the man shape at the top of the puzzle.
As to difficulty, it has to be rated as fairly easy, particularly for anyone who is familiar with the Horseshoe puzzle. It would be a good choice as a starter puzzle, but would provide very little challenge to an experienced puzzle solver. It would be a great choice to bring out to challenge a group of people as an ice breaker or table topic.
You can purchase this puzzle and get the solution at Puzzle Master.