Stardew Valley created by ConcernedApe.
Images used for educational purposes only.
Main Walkthrough

In order to trigger this quest you need to make it all the way to Winter. On the second day of Winter you’ll get a letter from Willy, challenging you to catch a Squid. Tricky prospects.

Squids can only be caught in one area of the game, and that’s down on the beach, by Willy’s shack. They have two other prerequisites, as well: you can only catch a Squid during Winter, and you can only catch a Squid at night. Consequently, you have 28 days each year to complete the quest, and only a few hours each day to get the job done.

Ideally you’ll want to have a few levels in Fishing prior to tackling this quest, as well as at least the Fiberglass Rod and some Bait. Squid are wily creatures, and it can take quite a few tries to land one once it’s on your hook. Levels and better gear will offset the challenge a little. Wait until the lights go out - it will start happening around 7 - 8 pm - then head down to the docks near Willy’s store and start fishing. Keep it up until you catch a Squid.

Be ye warned! Because this quest forces you to fish at night, you may run pretty close to the latest you can be up at any given time, which is 2 am. If you hit 2 am your farmer will collapse into a snooze and wake up in bed the next day - with a healthy bill from Joja Corporation for their trouble. Yay. Rush home whenever you hit 12:30 - 1 am.

Take your Squid to Willy once you’ve caught one. (He often comes home quite late, so if you fish off of his dock you may catch him before he goes to bed at night.) He’ll give you 800 gold via your Journal.