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I'm trying to take lots of stuff, but I am using the D&D 5e encumbrance system, so I can't take much, and my horse can barely hold me.

I want to take a donkey as well to carry the stuff, but I don't think you can control two mounts at the same time - and if I get into combat, there's no telling what could happen to the donkey.

So my idea was to fix a grappling hook to a chain, tie the end of the chain to the donkey, and just hold the hook to control the donkey - but if I get into combat, it's going to be hard to hold onto that and fight. So if I do get into combat, then throw the grappling hook into a tree so the donkey can't run and the bad guys can't steal it. And then I just pick it back up when I'm done and continue on my way.

Would this work well?

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    \$\begingroup\$ The problem I find with this question is that it's asking about your assumed solution to a problem rather than your actual problem. If the problem you're having is something along the lines of "I want to have a pack mule tied/lead by my horse that I can quickly detach if I get into combat" you should ask about that and ask how you could achieve that instead of asking whether your solution would "work well". Questions here generally work better when they focus on the actual problem, not the assumed solution to that problem. \$\endgroup\$
    – Purple Monkey
    Sep 20, 2018 at 1:05

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You don’t need elaborate schemes for this. This has already been solved by history, where how to use horses and pack animals has been well figured out.

Just like horses are trained to take a rider, donkeys and other pack animals are trained to follow the animal in front of them. This lets one person direct an entire line of donkeys that are tied together:

A silhouette of a pack train of donkeys lead by a mounted rider

This is called a pack train.

You tie your donkey’s lead rope to your horse’s saddle horn (that’s what it’s for!), and the donkey follows. Use a quick-release knot for emergencies and you can ride into battle at a moment’s notice, and track down the donkey after. When you aren’t surprised by a fight, you tie the donkey up beforehand.

This is how real horses and donkeys were and are used together.

RPG fans tend to be fans of studying useful bits of history too, because learning how our RPG characters’ stuff was actually used in real life gives us strategic ideas and advantages.

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  • \$\begingroup\$ so the donkey will chose stay put while the battle is going on? \$\endgroup\$
    – Nathan Santee
    Sep 20, 2018 at 1:03
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    \$\begingroup\$ Maybe if it’s stubborn or the fight doesn’t come near, but sometimes not. The more of them tied together, the less likely they are to go far. If you survive the fight tracking it down after (as mentioned in the answer) isn’t hard. If you don’t survive, it doesn’t matter. Generally, the strategy is to not get ambushed. \$\endgroup\$
    – SevenSidedDie
    Sep 20, 2018 at 1:07
  • \$\begingroup\$ I don't have any tracking skills \$\endgroup\$
    – Nathan Santee
    Sep 20, 2018 at 1:12
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    \$\begingroup\$ Many pack mule and horse trains have their entire animal stock with "blinders" on. It's thos opaque plastic glasses that are put in front a flight animals eyes to prevent stressful situations. If you have ever taken a city carriage ride, you've seen the blinders. \$\endgroup\$
    – Play Patrice
    Sep 20, 2018 at 1:24
  • \$\begingroup\$ @NathanSantee suggest you read the PHB. There is no skill system in D&D 5e. Any player can try anything; they are ability checks. If you have a proficiency in, for example, Survival, you may have a better chance at tracking, but any PC can make the attempt. Look up 'Using Ability Scores.' It is in the PHB. Also, be advised that "read the book to me" questions are not on topic at this site. \$\endgroup\$
    – KorvinStarmast
    Sep 20, 2018 at 3:30

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