• John J. O'Hara

How to Make Keeping Watch Fun in Dungeons & Dragons

Keeping watch is one of those adventuring routines that is rarely explored to its full potential. The Dungeon Master (we call them Quest Masters) informs the players that night is falling or that they’ve completed their eight hours of travel, and the players set up camp. Then the Quest Master (QM) asks, “Who’s taking first watch?” and they roll for random encounters. The party might be attacked in the darkness, they might be startled by a false alarm, or they might experience an uneventful, restful night.


Because of the routine, mundane nature of long rests and watches, some groups prefer to gloss over travel entirely and focus on encounters rather than exploration. But if you’ve ever read Fritz Leiber’s Fafhrd and the Gray Mouser stories, you know that all of the fun character moments take place in the lulls between the action.

Before Night Falls

Are you expecting to spend the night in the wilderness? Before leaving town to venture into the forest, ask the locals about the creatures that are active at night. Of course, the information you get from NPCs might not always be accurate! Then, rather than making a generic passive Perception check, you can actively listen (and look, if you can see in the dark) for these particular threats. You could also ask if your Wisdom (Nature) skill could help you distinguish between harmless and dangerous creatures.

Hirelings aren’t as crucial to a party’s success as they were thirty years ago. However, if there aren’t any PCs with Darkvision, it might be a good idea to hire a couple of NPCs with that ability to help with watch duties. Elves are a particularly good choice since they only need 4 hours of rest per day (though there is some confusion surrounding this rule).


If you can’t afford hirelings or don’t want them around for some reason, a couple of guard dogs are a useful alternative if you have someone in the party with the Wisdom (Animal Handling) skill. Of course, those hirelings (and guard animals) might be more reliable if they feel like they are part of the adventuring party. Before their shift starts, bring them over to the campfire and spend some time with them while you eat, drink, chat, and use your tool proficiencies.

Keeping Watch

If you have a large party, keep watch at least in pairs, focusing on opposite ends of the camp. In a party of four, however, you’ll only be able to keep watch one at a time if everyone is to get their 8 hours of rest since characters can only keep watch for a maximum of two hours during an 8-hour long rest period.

Sometimes, though, only one or two party members will need the full 8-hour rest: the wizard may need to recover spells, but everyone else needs only a short rest. In that case, the characters who do not need the long rest are not shackled to the “two hours watch” rule.

There are no penalties in 5e for sleeping in armor, so don’t bother getting undressed when your watch is over. Enjoy your steel pajamas secure in the knowledge that you’ll be ready to defend yourself should a problem arise during the night.

Playing Your Character

The open-ended nature of downtime affords some freedom concerning role-playing. When it’s your turn to keep watch, that’s a great time to bring your character’s quirks and flaws to life so they’re not just words on a character sheet. For example:

  • A rogue shares a dark secret with another PC while the others are sleeping

  • A cleric is roused from sleep to take watch but was in the middle of a prophetic dream and feels compelled to tell someone about it

  • A high-Intelligence, low-Wisdom wizard elects to read a book by candlelight rather than keep an eye out for enemies

  • A bard decides to practice drum rudiments during a particularly dull watch, potentially attracting an unwelcome audience

It’s always fun to let your character building talents shine in moments like this, but for the more extrinsically-motivated players, there’s still the possibility of inspiration points for good role-playing. When I’m running the game, I love it when a player role-plays their character’s flaws even if it leads to tactically-disadvantageous results.

You can also showcase your character’s personality and abilities while keeping watch in more productive ways. Your wizard sends their bat familiar out on patrol, watching over the camp through the bat’s eyes (or ears). The party’s Beast Master ranger, not to be outdone in the magical pet department, paces the perimeter with a wolf companion. The results might be the same with or without a familiar or animal companion’s help, or it might lead your Quest Master to come up with some interesting complications when the creature spots a potential threat.

These are just a few ideas for injecting some fun into this otherwise routine activity. What will you do in your next game to make keeping watch more than a tedious necessity?

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