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| Art by Peter Jackson (Not that one) |
Background
Sir Ascanio di Tolceda and Sir Michal Klerke are two knights who have long been friendly rivals, with a long history of comparing their heroic exploits and seeking to one-up each other at every turn. Both of them believe in the virtues of knightly valor, and hold that glory in battle is one of the finest pursuits a knight can aim for. To that end, they are firm believers in the tradition of pas d'armes, and they and their followers have been engaged in many a duel before. This time, however, the two knights have arranged a contest far beyond anything they've pulled off yet.
The two knights and their retinues have come to a well-traveled bridge and determined that it shall be the site of a grand tournament. No knight may leave until everyone on each side has fought everyone else in a joust; only then will one be able to determine their men are the greater. All the knights are stoked with the fires of competition, and no one dares to disappoint their liege. They are determined to keep to the tournament and see it out to the end, and will not move from the bridge until it is over.
The problem is, both rivals have shown up with a great host of knights, and the tournament has already raged for several days, with no sign of slowing down. And there are plenty of travelers looking to cross the bridge, only to be held up by the dueling knights. The people are growing restless...
The Encounter
This encounter should be used while the PCs are traveling on a major route that gets a lot of traffic, such as an important trade or pilgrimage route. As they approach a bridge, they notice that the path is backed up with a considerable number of travelers and carts - and they look frustrated and listless. The side of the road is lined with vividly-colored pavillions, where men are polishing their armor and squires can be seen tending to horses. Up ahead on the bridge itself, two knights in full armor are charging at one another along the length of the bridge, lances drawn, while their associated retinues and companions cheer from the sidelines.
If the PCs speak to the travelers, they will relate that the knights have been jousting for the last three days, and this has slowed traffic over the bridge. Some of the travelers have been waiting for hours to cross, but every time one knight is unhorsed, another joust begins. They've tried speaking to the knights, but none of the travelers are of noble class, and the knights won't listen to them, feeling they have no understanding of the demands of chivalry. The travelers request the help of the PCs - maybe they stand a better chance of getting through to them, especially if there are fellow knights among them.
The knights insist that their tournament is a matter of great importance, and they are not willing to put it on hold for anyone, nor are they willing to leave the bridge and admit their cowardice. Besides, they've already set up an extensive camp and it would be a lot of work to move it. If the party tries to ask the knights to leave, they will only hear a PC out if they are themselves a knight or noble, and even then, they had best have a persuasive (or deceptive) enough argument. However, if presented with direct orders from a noble of higher rank (such as a count, duke, or king), they will defer to authority.
The PCs might have better luck if they try to meet the knights on their own terms. If asked, they will be led to Ascanio and Michal, who are serving as judges for the tournament and overseeing the bouts. The two knights will gladly allow the PCs to join the tournament, and will provide armor, lances, and horses for anyone who does not have any of their own, but expect them to be returned at the end of the tournament. The two knights will both encourage the PCs to join their respective team, attempting to win them over with grand accounts of their heroic deeds. Even though they are rivals, they respect each other as knights and will not dare to besmirch each others' honor. They just insist that they are clearly the superior knight to support.
To make things more interesting for the players, both knights are in the possession of a magical artifact that they are willing to surrender to anyone who can best them in a joust. Sir Ascanio has a lance that grants Advantage on all attack and damage rolls as long as the attack is made from atop a horse or other steed, while Sir Michal has a helmet that grants the effect of a set of eyes of the eagle when worn. You may also want to have one or both knights be in the service of noble houses or other factions in your campaign - siding with one or the other may impact a PC's standing with those factions.
You can potentially stretch this encounter out into an entire "tournament arc," with the PCs facing off against multiple opponents. Some of these opponents could be knights they have previously encountered in the campaign or have preexisting relationships with. Furthermore, the PCs might face off against knights in the tournament that could become recurring rivals later down the line. If you want an encounter that you can resolve quickly, though, you can simply have the PCs challenge one of the rival knights directly, and he will agree to withdraw from the bridge if he is bested in a joust. All competitors can be assumed to have the stats of a knight, and use warhorses as mounts.
Several people have written jousting rules for 5e, so feel free to use whatever system works best for your table here. I was going to list a set of my own, but in researching the subject, these rules are pretty close to what I would use anyway, so I'm just going to leave them here.
Alternatively, the PCs could try looking for an alternative route around the bridge. This route, however, may prove to be a deadly and treacherous one, and the travelers may want to come along too to scope it out. This could turn into an escort mission for the PCs.
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