The Trickiest Side Quests from Red Dead Redemption II

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Red Dead Redemption II is absolutely full of side quests, extra stories, and Easter eggs. It’s the perfect game for procrastinators as if you’re ever a little tired of the main storyline, there are endless distractions.

If this sounds like the kind of gamer that you are then we’ve put together a real treat for you. These are some of the trickiest adventures in the game and none of them are mandatory for success. To put it bluntly, these are the most enormous wastes of time, but you’ll have good fun completing them and bragging rights once you’re done.

Red Dead Redemption II

The Gambler Quest

Kicking off with what is widely accepted as the most difficult of the challenges, The Gambler Challenge gives you a whole series of goals to complete. These start off pretty simply, asking you to win three games of Five Finger Fillet.

While this game might be downright dangerous, anyone who’s spent any time horsing around on Red Dead Redemption II knows that it’s fairly easy to win if you take things slowly. However, after this, things start to get trickier.  A lot of people struggle with doubling down and winning the hand five times in blackjack, but there’s a simple tip to help you and that’s to practice the game on its own.

Playing at an online casino can help you hone your blackjack skills, so that you can attack the gambler challenge with confidence. If you think that this method could help you in your undertaking, it’s possible to play online at What’s more, you can also practice other games there too, including poker, which will be necessary to tick off the achievement of winning five hands in a row. With the gambler challenge out of the way, the remaining challenges will all seem much easier.

Red Dead Redemption II

Finding the White Stallion

Early on in the game, you’ll likely be sticking to the main storyline fairly rigidly. However, if you do veer off course into the land of side quest procrastination then there’s one thing that you’d be well advised to do. As anyone who’s played will know, having the best horse that you can reasonably afford will seriously help you out in the game. In the beginning, you get given a horse who’s okay and you might even progress to the super sturdy black Shire horse from early on in the second chapter. However, neither your starting horse nor the black shire is going to stand you in good stead when it gets to the more complex chapters.

Unfortunately, there isn’t much better you can do horse-wise at such an early stage unless you get a little creative. There’s one horse who lives up in the mountains around Lake Isabella. You’ll need some warm clothing and a bit of stealth on your side to spot it, but once you do, it’s essential to tame it.

This horse is one of the true superior stallions of the game. Not only is it a stunning pure white Arabian, but it’s also faster and has better endurance than anything you can get until the final chapter. This might seem like a bit of procrastination, but it will speed up everything you do in the game afterward.

Red Dead Redemption

Oh, Brother Where Art Thou?

The Oh Brother quests are loved by some and hated by others, when it comes to ‘marmite’ quests, these take the title. Hopefully, you’ll be in the group that loves them, as we can’t resist this increasingly silly story. They begin with a competition between two brothers to win the affection of a lady. They’ll ask you to prove who is the manliest, bravest, and most suitable suitor for her, by getting you to complete a selection of progressively more stupid tasks. Initially, you’ll be shooting your gun through bottles on their heads, but before long you’ll be punching them in the face and gut, as each of them groans in pain.

The lengths that they’ll go to win the affection of this lady are commendable, but we can’t help but wonder if there might be better ways to go about it. Either way, they’ll keep popping up where you least expect them, which is what makes this quest so difficult.

Just as you think they’ve settled their differences, they’re back with another ridiculous request. If you’re not in the market for spoilers then stop reading here, because this next part is a big one. The final installment of the Oh Brother quest is a tragic one. The brothers will ask you to push them down a river in a whiskey barrel and Helen, the lady they’ve been fighting over will plead with them not to.

The first will survive the ride, but it doesn’t look good for the second. Along with Helen, you’ll need to gallop down the river to Cumberland Falls, where you’ll see the barrel tip over the edge. We’ll leave it to you to find out if the second brother is as lucky as the first.

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