Once a month or so, we’ll do a Random Monster Mashup! This could take many forms – maybe see what happens when the monsters fight or team up, think about what kinds of circumstances might result in this situation, and even, if we’re feeling really creative, think about what happens if we stick these two monsters in a teleporter together and hit “SEND.”
What happens when a screaming sky-predator meets a protector of Nature’s balance? On the one hand, you have a ravager of the skies, a small dragon that doesn’t have a lair full of gold, but rather one that hunts out in the world and brings terror wherever it goes. On the other hand, you have a person who is deeply attached to the natural world, involved in its growth and decay, the ebb and flow of natural cycles.

There are a lot of ways you could relate these two. My favorite is the “I Can Change Him” Druid. Some young person of the wild, maybe out in their earliest days of learning how to commune with the natural world, becomes enchanted by a Wyvern.
A druid like that, though, would be a light snack for a Wyvern. So the druid tracks the Wyvern, observes its movements. Perhaps leaves it little treats from time to time to gain its trust, all in the hopes that this big scaly murder machine might turn out to be a big ol’ cuddle bug after all.
It… it won’t be.
That might be where your Party comes in. A Druid circle is asking someone to find and talk some sense into this young person before they get themselves eaten. The youngster refuses to listen to their elders, but perhaps a neutral party can get through to them. Does the young Druid succeed in befriending their Wyvern and fight against the Party’s intrusion? Does the party manage to save the broken-hearted youth when they find out once and for all that Wyverns Are Not Our Friends? Maybe the Wyvern is a little smarter than its kin and is angered that your players are trying to remove a potential food source. That’s all up to you and your players, but it could certainly be a fun quest to put in front of them.
That’s one way their paths might cross. Here’s another: what need would a Wyvern have for a Druid? Well, Wyverns aren’t all that smart – their Intelligence tops out at 5 – but with a Wisdom of 12, that might just be enough for it to put a few pieces together and realize that this one human who lives alone and sings to trees might be the one to help them out.
This Wyvern might be sick. Or injured. Or fleeing from something that has destroyed all the other Wyverns in its area. It has faced something that fangs and claws cannot fight, but it knows there are tasty-looking two-legs out there who can be very dangerous indeed. So it comes to a Druid – maybe even your Druid – and asks, in its own proud, aggressive way – for help. Will your Druid help it? Will your Party even let it get a word in before they try to kill it?
Either way, a Wyvern on the run would be a great way to signal to your Party that there is something bigger and badder out there that they’re going to have to deal with at some point. Whether it’s an elemental incursion, a swarming army of undead, or a very pissed-off Tarrasque is entirely up to you. But as far as foreshadowing goes, a terrified Wyvern can do the job very well.
Finally, what happens if we merge the two? What would a Wyvern Druid turn out to be like? How would that even happen?
If we’re running as true to the rules as possible, a creature should have a Wisdom score of at least 13 to be an effective Druid – this is laid out in the rules for Multiclassing, so it’s a reasonable place to start. Our Wyvern comes in at a 12, just below the threshold.

But, as the young Druid in the early example might have said, we can fix that.
Our first thought might be the Awaken spell, but the Wyvern is actually too intelligent for that one. Without that, though, there are plenty of ways for a Wyvern to get that WIS boost. Perhaps a fallen adventurer had an Ioun Stone of Insight, a pretty, floaty, shiny stone that fascinated a Wyvern who came to feast on the body. With enough attention, the Wyvern became attuned to the stone, bumped it Wisdom up to 14, and is now a candidate for Druidhood.
There are plenty of items and story hooks that could justify making your Wyvern a little wiser and a candidate for being a Druid. That’s not really the important part. The important part is what kind of Druid they would be.
We often see Druids as protectors of the natural order. Flowery tree hippies who act as guardians and protectors.
What if a Druid were a predator? What kind of magic and tactics would a Druid bent on the hunt use? How would it reshape the land to truly become an apex predator? How could this vicious creature become even more terrifying when it has the ability to wield the magics of the natural world to hunt and ensnare its prey? And certainly a Wyvern that is that good at hunting would gather companions, followers, or hangers-on hoping that this powerful creature might just give them a chance at food as well. A predator that commands storms and roots, hunting from the sky with claws and conjured thorns becomes much more than an encounter.
That’s a legend.