I'm about to run the interaction with the party and meeting Ontharr Frume in Hoard of the Dragon Queen. I ran across this list and found it helpful: https://homebrewery.naturalcrit.com/share/Hk7UzfKA0e

I'm also coming up with a "card game" by rolling all six dice and being able to re-roll a couple times, or maybe "trade/bargain" with other players for a "card" that they want--but I'm trying to keep it from getting too complicated...

But I thought I'd ask the forum anyway...does anyone else have good resources for the sorts of things characters might do in a bar/competitive environment among friendlies that they have found that their players really enjoyed?

I actually wrote up some extremely simple games and characters for this exact scene. Nothing particularly complex... most resolved with a very basic skill check, but I'll go ahead and post what I wrote up:

Order of the Gauntlet

They have a hidden room in the tavern, “A Pair of Black Antlers”. The tavern is attended almost entirely by Gauntlet members… they’re known for being rowdy and boisterous, but they’re not criminal and it’s considered a safe location for most, but criminal activity is harshly punished without hesitation. Order members are known by the symbol of the order: a Gauntlet grasping a sword by the blade, representing the focus on defending others rather than violence for violence sake.

Skronk – A rare goblin Paladin. He has a chip on his shoulder to prove his place. He’s the arm wrestling champion and challenges anyone who questions him or his position as a Paladin. He has a +6 to athletics, and players must succeed on 3 contested athletics rolls to beat him. He has a Passive Perception of 12.

 

Tasar Phiyra – Classic elven ranger. He’s tall and elegant, unaware of how egotistical he sometimes sounds. He challenges the players to darts. He has a +6 to attack… he and the player take turns attacking a target with AC12… the first to miss twice loses. Passive Perception of 16

 

Dwigt Rotrugal – Human knight who loves to gamble, focused mostly on playing dice. He plays a simple game of dice… roll 3d6, highest number wins. He is testing the party’s bravery or perception more than testing their skills. Players succeed his test if they bet 25 gp, regardless if they win… or if they make an otherwise impressive bet. Dwigt cheats, with a +4 to Sleight of Hand, and if the player catches him he rewards them 5gp. Similarly, if he’s not caught, he returns the money lost when the party is allowed to speak to Ontharr.

 

Dean Wesrey – Human bartender. He organizes a drinking contest. The players must make a DC5 Con Save… then 10, then 15. If they succeed all three its considered a success.

 

Onson Sweemey – Half-Elven bandleader who plays a violin. She has a +8 to performance. A group of gauntlet members and civilians are gathered on the dance floor. If party members start dancing, she begins to play a complex song, requiring a DC15 performance check to impress him and succeed another challenge.