Googling around in regards to 5E D&D rules I found a thread where a Dungeon Master was actually complaining that since in 5E players can by RAW jump their strength in feet that meant all 10-foot pits were now not a challenge to the party. Somebody else chimed in and cleverly said ‘well, in a world where you can easily jump 10 feet all pits would be 20 feet long.’
I’m sitting there in my underwear thinking why the hell does anybody think that a ten-foot pit is an interesting or exciting challenge for a party?
What group of players after a game go, ‘Holy shit Dave when we came to that ten-foot pit in the tunnel we were stoked, then when Jim rolled a 9 and fell in we all shit our collective pants as he took 1d6 damage. Then we had to watch him roll 3 more times to try to climb out. That was intense.’
I fondly remember playing in a game where the GM took railroading to the point that all he really let us do was literally wander in one direction through a tunnel fighting mob after mob of orcs. It was 4e. They were dark times. We said after the fourth or fifth orc fight that this was getting a little stale so the DM brewed up a surprise for us. We fought some more orcs and then came to a ten-foot pit in the tunnel! That lead to…more tunnel…Yes we thought as we collectively orgasmed, now are we in for some exciting adventure.
I was so frustrated by this point that I jumped down the pit. The GM said that was stupid as it was like at least 100 foot. I said it didn’t matter I had feather fall. He had no idea what to do bless him. I asked what was down the tunnel or where I could go. No clue. Entirely frozen. All he could do was complain to the other table about how stupid I’d been. I left after that and never came back and I can still picture my wizard wandering through those tunnels trying desperately to find something interesting.
The issue is the decision is often utterly binary, you either jump over the pit or you fall and lose some hit points and climb out again. There’s no decisions to be made beyond whether to jump over it which if it blocks your way you don’t have much choice about. Unless you want to be the adventuring party who return to the King saying ‘Sorry, the Kobold’s have probably eaten your daughter now, there was nothing we could do they had a ten-foot pit.’ Hence why being able to circumvent most pits automatically in 5E makes sense. It’s pretty much a trivial task that shouldn’t interrupt the flow of the game to overcome unless it is actually designed to be more engaging than that.
So how do we make pits interesting and engaging?
Pit them in a combat.
If you make the pits part of a combat then they provide an interesting obstacle for the players to circumvent or kick hapless orcs into, whilst they clash swords. If the tunnel combat above had actually included the pit as part of the constant fights with orcs then it would have been far more interesting, we could have lured them towards the pit, or crossed the pit and picked them off with ranged weapons as they tried to cross it and so on.
Pit interesting things in the pits.
Placing a secret door which leads towards another part of the dungeon, or simply a storage room for the Kobold’s treasure, at the bottom of the pit will encourage players to interact with pits beyond just rolling dice at them and moving on. Placing elements into your game that encourage exploration and diversify environments is always a good plan as it empowers players to approach things in interesting ways. In my above example, it would have meant that my feather falling wizard would have actually been able to find something interesting when he jumped down.
Ten-foot poles love ten-foot pits.
Part of the problem with pits is that is they get reduced more often than not to an Athletics roll. Back in the day before a homogenised list of skills existed you used to have to actually think about your environment and how to interact with it. Items such as ten-foot poles in your inventory could be used to circumvent things like ten-foot pits. You could use it to pole vault over the pit for example, or simply place it over the pit and quickly run across it, or to fish out the hapless characters who find themselves stuck down the pit. So encouraging player ingenuity in overcoming obstacles is one way to make them more interesting challenges than just rolling an athletics check would create.
All this advice applies pretty much to any trap you want to throw at the players I just find pits to be rather a ubiquitous example. Hopefully, that gives a little inspiration on how to jazz up the humble ten-foot pit.