"If I would've gone to Canada, I'd have had to have some kind of winter gear."

would have gone <-> would have had -- same tense.

Your version would mean: If I had gone to Canada (earlier), I would (now) need to have had winter gear (back then). Which doesn't make much sense.

If I would've gone to Canada, I'd have had to have some kind of winter gear.

"Would have gone" ↔ "would have had" — same tense.

Your version would mean: If I had gone to Canada (earlier), I would (now) need to have had winter gear (back then). Which doesn't make much sense.