On his first arrival, Mario finds that the town is cursed by Doopliss, turning the villagers into pigs every time a bell rings. He also finds the fourth Crystal Stars there. Obtaining it gives him Art Attack. It is a town that is very dark and depressing as the people are too. With Vivian's ability to make Mario and her invisible, they can eavesdrop on the crows, which gives important information. Apparently the Twilighters, although seeming to be miserable, are quite happy with their existence, as Darkly, the only Twilighter to be seen outside of the town, says he prefers dark and dank places (He is found behind some houses in the east side), and the innkeeper in the town tells Mario to "Have a nice twilight".
To pass onto the Twilight Trail, Mario must pass the gatekeeper, but he needs the mayor's permission. When you go back to Mayor Dour, he's a pig, and when you go to the gate, so is the gatekeeper! So Mario passes and can go into the barn to get a key, then uses Koops to get another past a tree log. He returns to the shop and goes into the storage room where you get another ability. Mario can use it to get past the tree log and go onto the Twilight Trail.
If Mario wins he gets it and runs off with his partners. But Doopliss steaks Mario's body and friends, impersonates him, and steals his name. When he returns to the village, he finds Superbombomb, a bomb for Vivian that doesn't work and she comes to help you. Whenever you try to pass the small barn area, Doopliss challenges you and no one can take damage. You must run away to pass. That well is full of Buzzy Beetles, which there are 15 that all attack at once. He can push a door after defeating them all which you need Vivian to pass, which you can then find the letter 'p' you need to spell Doopliss' name and you hear his name. He also picks up a few keys and other items there before returning.