I mean, I do love Skyrim, but come on: "You must travel half way across Skyrim to kill a bear". I could cope with it being a one off quest, but as Harbinger of the Companions I should be above this stuff!

I dunno.

The Whispering Door is a strong contender in the "What? That's it?" category.

The entirety of Craglorn quest design in ESO easily wins in "Do you even know why people are playing your game?"

Blood on the Ice is a worthy successor to TES II: Daggerfall in "[censored] it and [censored] Bethesda's QA dept."

Gaenor in Tribunal might very well be the most frustrating enemy ever (the first time you face him, at least).

And who could forget Falkreath's epic Delivery quest: take this urn of ashes and walk down the street. Oh, my hero! *swoons*

You. I like you.

I'd say the worst quest in the Elder Scrolls is "No Stone Unturned" for Skyrim.

Seriously. It's a meta-quest that requires you to play something like 90% of the basic game to complete. All for a trinket that you can only see in the Theive's Guild trophy room and a increased chance to find gems in loot. Which would've been a very nice thing if you weren't at the point where you're already richer than the Emperor and have little to spend all that wealth on.

Oblivion's Nirnroot quest was better. There were more than 100 nirnroots in the game, and you could easily complete the quest without being forced into other questlines. This is not true for the Stones of Barenziah

Even more silly for my character today. Got the quest from Thadgeir when he was sitting at a table in the inn next to Runil. Easiest 250 gold ever.

Well the one where they send you to kill an escaped criminal isn't much better.
"Ok, I'll do it, but where is he last seen? How he might look?"
"Ah quit your bellyaching.. He has his GPS on ! "

It may not be particularly intricate or suspenseful, but I don't think it's anywhere near the worst. Travelling all across Skyrim to fight/kill things they've been asked to is what the Companions do.