Changing Of The Seasons
Finish the four dream sequences.
At The End Of Everything
Unlocks after the credits.
See section below.
Mess up on all of the songs in one playthrough by not touching your keyboard/controller or smashing random buttons.
You “only” need to play all three songs at an okay level. While the first two ones are doable with practice, the third one may be troublesome. If you, like me, used a controller to play the game, consider switching to keyboard! I got a pretty good on the third song on my first try after remapping the bass strings to HJKL.
Just beat Demontower, which is a minigame on Mae’s laptop. Doesn’t matter which ending you get. However, I suggest you go for the good ending which will give you 2 achievements at once (see Palecat).
Beat Demontower and get the good ending. DON’T kill the bird that spawns during lv. 2; he will give a hint every 2nd level for which skulls you need to activate on lv. 10; beware the order! After you activate the skulls in the correct order, a tomb with a key will spawn. Pick up the key, go up to the big corpse and use the key to close the wound. Then proceed to beat the final boss and voila!
Hold Onto Anything
Beat the game a second time. For some people it currently only works if you hang out with ONLY Bea or Gregg.
Hang out with Germ under the bridge and come back and sit on the bridge later. After a while, Rabies the Trash King will show up and the achievement unlocks after you talk to him.
Look at stars with Mr. Chazokov. He will hang out on top of the poet’s house on some days; just check every morning and on the last day! After you hang out with him 5 times (9 constellations in total), the achievement should unlock.
Keep checking grandpa’s bookcase after Halloween (next to the bird cage in Mae’s house) and at some point you get some numbers. You will also have to bug your dad to move the boxes in the room underneath the stairs; keep watching TV with him (3 times). After he moves things out from the room (the game will let you know when), go in there, crawl to basement, open the lock, and grab the tooth. You also need to go to the library with Bea to learn about the tooth by reading a newspaper clipping on miners and strange teeth. On the last day when you talk with dad outside the front door, Mae will give him the tooth and the achievement will unlock.
Poets Of Possum Springs
Talk to Selmers (the bear in the pink hoodie) and listen to her poems everyday. When you’re done with the research at the library, the Poets of Possum Springs will read their poems next to the reception desk. Listen to the poems for the achievement.
Best Available Friend
Hang out with Bea instead of Gregg. Follow her storyline (mall, house call, dinner, college party); it will unlock after the college party.
During the pizza eating scene, only eat the leftover crust.
Mother Of Vermin
Feed the rats one pretzel from the pretzel stand. Climb the powerlines to the left of the stairs to the church, follow them until you get to the building with the “Nuke Possum Springs” graffiti. Get on that building, then go all the way to the right until you reach a half-open window. Climb inside and you should find the rats inside a deceased mascot!
Same as above, just feed them over the course of three days and they leave the nest to cause a major rat problem.
Talk to Lori on the rooftops every day/near the war memorial and go to the train with her every time. The achievement pops after your last talk. To find her, follow the route outlined in Mother of Vermin, but continue right and keep climbing until you see a mouse chilling on the roof.
Let’s Be Legends
Hang out with Gregg instead of Bea. Follow his storyline (Food Donkey, parking lot, woods, donut shop); it will unlock after the donut part.
Shoot the target in the head when in the woods with Gregg during his storyline.
You killed that poor roach.
When you find the arm on the ground, there’s a roach running around that you can poke and squash with the stick.
Deep Hollow Hollerers
Get the two lonely musicians together. One is in the secret stage (top of tall building near the Snack Falcon), the other will appear on the rooftops not long after Harfest. Talk to the violinist first both days, then go see them on the stage on the third day.
Thryy Wyrd Tyyns
Talk to some weird teens hanging out by the cliff past the church during Halloween. They give you a side quest to find 3 pentagrams. The first is if you go to the out of town party with Bea and talk to the punk girl in the back of the room OR order Doomnuts with Gregg during his storyline. The second is in the secret stage (see above section). Third is at the very end in the mines. The achievement unlocks the next morning.
Win the knife fight against Gregg in the forest. You just need to win most rounds.
Accidentally Good Dinner
Go shopping with Bea after work one night and pick out chicken, biscuits, mac n’ cheese, and cream of chicken soup for dinner. Avoid the Bake and Shake! This is just one of many possible dinner combinations.
Talk to your mother everyday at church when you get access. When she asks you if you want to get out of there, say yes and finish the event.
He’s from somewhere.
Hang out with Germ whenever you can before you go hang out with Bea/Gregg. When everyone groups up at Gregg and Angus’s apartment, he will strike up a conversation before leaving, and it will unlock.
Fill out your journal completely by getting all doodles over multiple playthroughs.
Make It Last
Seems like you have to do most major things. Can be done in two playthroughs.
Things you may have to do:
– All friendship quests (including Germ)
– All investigations
– Release the letters from the windmills
Stuff you seemingly don’t have to do:
– Beat Demontower