Gambling and Festival Games

My players are headed for a huge festival, and I want to make it an immersive experience for them, so instead of just narrating the festivities I developed these mechanics for games of luck and skill. Hope you enjoy and find useful.

Gambling Games

Three Dragon Ante

  • Players ante in (set ante or rising bids)

  • All players roll a d12; reveal to DM but otherwise keep secret

  • Round of betting & contested Insight vs Deception checks (DM narrates the gamblers’ “tells” for successful Insight checks, but shouldn’t reveal the actual hand; e.g., “He’s trying hard to keep a straight face, but his firmly suppressed smile tells you he might be sitting on a good hand.”)

  • All players roll another d12 as above

  • Round of betting & contested Insight vs Deception checks

  • All players rolls a final d12 as above

  • Final Round of betting & contested Insight vs Deception checks

  • Winner takes the pot

  • Three 1s is the best hand (called Three Dragons), followed by three 12s, three 11s, three 10s, etc.

  • A pair of 12s is the best pair hand, down to a pair of 1s

  • If no pairs or threeways, highest sum wins

Three Headed Hydra

  • Numbers Bet (pays 1:1, 2:1, or 10:1): the player picks a number between 1 and 6; increasing payout for the number of dice that show that number

  • Over (pays 1:1, does not pay on a jackpot): the sum of the dice will be over 10

  • Under (pays 1:1, does not pay on a jackpot): the sum of the dice will be under 11

  • Jackpot (pays 30:1): all dice show the same number (do not need to specify number)

  • Three Headed Hydra (pays 100:1): pick a number between 1 and 6; all dice show the specified number


  • Two players play as a team against the house; minimum bet is 5gp per player (10gp total buy-in)

  • The house rolls 1d20; the result is the Highwayman

  • Player 1 rolls 1d20

  • If player 1 rolls below the Highwayman, player 2 must roll above the Highwayman; if player 1 rolls above the Highwayman, player 2 must roll below the Highwayman; if both players roll the same number as the Highwayman, this is called robbing the Highwayman and has the largest payout

  • If the house rolls 1 or 20, the only possible win is robbing the Highwayman

  • Regular wins pay 2:1; robbing the Highwayman pays 200:1


The payout from most of these games comes from the winner being paid half the total bets placed by spectators of the contest, called the purse. Feel free to adjust to fit your own setting and scenario.

Catch the Greased Pig

  • 1cp per try

  • Contestant begins inside a 25×25 pigsty with a greased pig

  • Contestant must capture (grapple) the pig and hold it for five seconds

  • Contestant has 30 seconds (5 rounds) to catch the pig. Holding it for five seconds can go into the sixth round.

  • Combat initiative for contestant and pig

  • The pig will always move up to its full speed on it turn, then ready movement to move away if the contestant comes within 10 feet

  • Pig has advantage on grapple checks

  • Winners get a free gallon of ale

Arm Wrestling

  • Buy-in is 5sp.

  • Contestants begin with a number of points equal to their strength modifier

  • Contestants make a contested Strength (Athletics) check. The loser loses one point. Repeat until one contestant loses a contested check while having zero points

  • The first contestant to lose a contested check when they have zero points loses the arm wrestling contest.

  • Winner gets the buy-in plus 1d10 gp (half the purse)

Tug of War

  • Entry fee of 10gp per team

  • Teams of X contestants, where X is the number of players who want to compete together

  • Teams begin 15 feet from the mud pit in the center.

  • Each team makes group Strength (Athletics) checks; sum the results into one score for each team

  • The team with the lower total score gets moved 5 feet toward the middle

  • Repeat until one team is pulled into the mud pit

  • Winning team gets buy-in plus 2d10gp (half the purse)

Archery Contest

  • 10gp to enter, minimum 3 contestants

  • 3 shots with a short bow at 50ft and 3 shots at 100ft (with disadvantage)

  • Standard archery scoring

Wooden Sword Fencing

  • 5 gp entry fee; duel or battle royal

  • Combatants choose between longsword style or rapier style swords (proficiency bonus to attacks if they’re proficient with that weapon; rapier style is finesse)

  • Standard combat rules

  • Hits do no damage; if you take 3 hits you’re eliminated

  • Duel winner gets entry fee + 2d10gp (half the purse)

  • Battle Royal winner gets 75% of the entry fee (number of combatants x 5 x 0.75) + 5d10 gp (half the purse), 2nd place gets 25% of the entry fee.


  • 2gp entry fee, 2 contestants

  • Standard combat rules, unarmed strikes only, no armor

  • Winner gets buy-in plus 3d10gp (half the purse)

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