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I have seen multiple forum posts where users state that you need to defeat the main bosses on Cyclops Lane, Triton Avenue, and Firecat Alley, and the Headmaster will give you the quest to go to Colossus Boulevard. I have defeated almost all of the bosses in those streets, and the quest has not unlocked.

What are the requirements to get into Colossus Boulevard?

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  • I had also did this, I just kept going with the main quests. Seemed to solve it.
    – Codingale
    Aug 22, 2017 at 14:38

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You have to defeat almost all the bosses in Wizard City

Defeat the Harvest Lord, the Kraken and Sergeant Skullsplitter (all of whom are located in Triton Avenue).

Complete Cyclops Lane by defeating General Akilles and Eyus Maximus.

Vanquish all enemies located in Firecat Alley (Melweena Smite, Bastila Gravewynd, Alicane Swiftarrow and/or Wormguts).

Venture to Olde Town and defeat Foulgaze in the field of battle.

Obtain 750 crowns or purchase a game membership. Without one of the two, you cannot enter Colossus Boulevard.

Speak to Merle and he will send you on a quest to find Private O'Doyle. The private has the key to Colossus Boulevard.

Here you can read throught all the information given on this subject from itstillworks

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