For all native English speakers, this is how the rest of us feel about any words in English

Is that the one pronounced "Wooster"?

There was a YouTube video I watch ages ago and it explained it pretty well.

The differences depends on who settled the town. Roman, Saxon, or Viking

I have American friends who couldn't pronounce it. it was always some variant of "Glow-kester-sheer" but tbh I can't blame them, the spelling doesn't do the pronunciation justice 😂

In his comments on the Jeeves & Wooster series Stephen Fry talked a bit about English family names. Among others, he said Mainwaring is pronounced "Mannering", and Cholmondeley is "Chumley".

Glaw-stuh-shur, correct?

When I was on vacation with my father in Scotland we wanted to see the highland games in Glenisla. We needed directions or needed to know the exact date when they'd take place or so, so we went to some tourist information. That poor girl there had no idea what we wanted when we asked about glennis-law. But she soon figured out that we meant glen-ila.

The highland games were awesome, btw!