Shovel Knight: Specter of Torment

If you go up one room from Specter Knight's starting point in the Tower and break through the left hand wall, you will find the NPC, Horace. Horace will challenge you to a race to the top of the tower. This race is special in that the game has a number of preset sections that it randomly chooses and pieces together to create the "racetrack". In other words, if you fail, you can always try again in hopes of getting a different loadout for the race. Although no curios are required to complete the race, there are certainly some that can help you out. The most notable ones being the Hover Plume, Judgement Rush and Chronos Coin (see Spec'd Out. There is no cost to try and if you complete it successfully, you will win some gold and this trophy/Feat.

Here is a video example of one run that I completed: