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An entry into Fortnightly Topic Challenge #46: "Tales From the Cryptic"

THE QUEST

I have been running a role-playing game, in which my friend plays a halfling named Ptolic. Recently, Ptolic wanted to get ahead in the (fictional) world and join a certain guild in their home city. In order to have them prove their eligibility, the guild offered Ptolic a challenge: Enter the Maze of Hermes at night and find the magical token that has been hidden somewhere under the sandy floor.

Not to be discouraged at this slightly dubious request (my friends never trust me for some reason!), Ptolic spent their time in local inns and taverns trying to get some inside knowledge. This was tedious but rewarding, getting them not only a map but also a lot of juicy rumours that seemed to cryptically hint at how to navigate the maze! After some scribbling on the map, Ptolic felt well-prepared to set out.

It was just before midnight as Ptolic began tracing the path from the NW corner of the maze, carefully leaving both the labelled statues to Hermes and the marked traps undisturbed. Using all their skills, abilities and equipment, they arrived at the end of the path (f7) but, after a long and thorough search, the token was nowhere to be found! Clearly, something had been overlooked on the map (and it isn't that I am just a mean GM)!

  • Can you complete Ptolic's map?
  • Where would you advise Ptolic to dig?
  • What guild do you think Ptolic wishes to join?

THE MAP

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THE RUMOURS

  1. Retreat! Back up! Winged Mammals! Hurt them while they aren't looking! (8)
  2. Allure of lucky token. (5)
  3. Cloak partner in tatters, switching parts of fringe. (6)
  4. Agility from listening to packs of cards? (3)
  5. Viper producer - get out of the way! (5)
  6. Light armour material from pasture on the right. (7)
  7. Choose Mark Edward Tollbury, initally, to steal from passers-by. (10)
  8. Light sword parried, whirled and dropped down. (6)
  9. Stealthy character starts out to run reconnaissance. (5)
  10. Snake writhes to move silently. (5)
  11. Dash to the operator and knock sharply. It will catch you unaware! (4)

THE THANKS

@bobble, for the puzzle inspiration - even if you don't remember giving it!
@Deusovi, for testing the puzzle - even if I was testing your patience with lots of questions!

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    $\begingroup$ I think this is well deserving of the [story] tag and entry into the FTC! $\endgroup$ – bobble Jan 5 at 4:18
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    $\begingroup$ Quadrasect the map with detect magic. You'll find it soon enough. $\endgroup$ – Joshua Jan 5 at 17:56
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Final answer (with help from @user39583 and @msh210)

Cryptic clues:

  1. BACK+STAB< retreat = back, back up = reverse, winged mammals = bats

  2. CHARM double definition

  3. DAGGER* cloak and dagger, tatters = ragged, switching parts of fringe = swap first and last (this one could be "dagger" or "ragged", but based on the theme, I think dagger makes more sense)

  4. DEX (decks) short for "dexterity" (agility) in D&D

  5. DODGE double definition (Dodge produces the Viper sports car)

  6. LEA+THE+R pasture = lea, then "the", right = r

  7. PICK+POCK+E.T. choose = pick, mark = pock, Edward Tollbury initials = E.T.

  8. RAPIER* "parried", whirled = scramble (rapierd), dropped down = remove "D" (rapier)

  9. SC+OUT stealthy character starts = "sc", then "out"

  10. SNEAK* snake writhes = scramble "snake"

  11. T+RAP dash in Morse Code = "T", knock sharply = rap (thanks @user39583 and @msh210!)

Can you complete Ptolic's map?

Starting from the NW corner and entering the clues, rearranging them to fit with the pre-existing letters (thanks to @user39583, who also made the image): Ptolic map

Where would you advise Ptolic to dig?

D5, where the "X" is (thanks again to @user39583)

What guild do you think Ptolic wishes to join?

Ptolic wants to join a thieves' guild; all the clues are related to the rogue class in D&D in some way

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    $\begingroup$ rot13(Qnfu, gb gur gryrtencu bcrengbe, vf G.) $\endgroup$ – msh210 Jan 5 at 15:11
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    $\begingroup$ @msh210 This is what I have: i.stack.imgur.com/IHhZ4.png and it seems to be unique with the rules I'm following? $\endgroup$ – user39583 Jan 5 at 15:17
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    $\begingroup$ @msh210 Right! You need to reorder the clues to match with the letters in the grid! $\endgroup$ – user39583 Jan 5 at 15:19
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    $\begingroup$ @user39583 makes sense, since the rumors were heard in arbitrary order! $\endgroup$ – msh210 Jan 5 at 15:39
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    $\begingroup$ Yes! This is correct! :) Awesome work! This is the only path that leaves the statues and traps "undisturbed" :) $\endgroup$ – Graylocke Jan 6 at 0:52

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