[hithereagain]

If you start with Mathematics, you'll end up in a loop: Mathematics > Quantity > Magnitude (mathematics) > Mathematics.

Ignoring this backlink, though, it would work:

Mathematics > Quantity > Magnitude (mathematics) > Mathematical object > Abstract and concrete > Referent > Linguistics > Science > Knowledge > Fact > Verificationism > Philosophy

[amenod]

Also, starting with https://en.wikipedia.org/wiki/2003_Internationaux_de_Strasbo... (random page) you get into loop around "Languages".

But if the algorithm should ignore the already visited links then it would probably work because the pages usually describe something using the higher level concepts first. The question is how much larger the pool of "always found" pages becomes.