I took on my first city- Appleton. Appleton is one of the "Big Three" along with Earton and Treeton. Because they are on the main isle, these cities are large and full of NPCs. Appleton is on the south end of horse isle. It lacks stores-feed, clothes and a general store, which leave the the others stores well stocked. It is, however, a huge stop for quests.
Those Who live there:
Sandy Flint: Sandy owns the rock shop. They have pretty good prices, and Sandy is in a few quests. I forget if Sandy starts any.
Nico Leash: Nico owns the pet shop. He's a great guy, has good morals about his animals-and a Donkey named Foghorn! He's in a few quests but none start here.
Kier: Kier is a little blackbird who lives on the water tower. He has a quest about getting him some feathers. Worth a visit.
Arthur Templeton: Arthur is a popular visit for quests, but I don't think he starts any. He's nice.
Charlie Trimmer: Charlie is my favorite groomer. He can completely groom your horse. He might be a stop in one of the quests.
George Napper: George is a character. If you really want to use an inn, visit Shelton. That's my personal favorite inn. George is just...George.
Patrica Plum: For some reason, I find I'm in this food store a lot. I don't know why, I am. Patrica is awesome, but my favorite food store is Treeton.
Rowena Roget: Rowena is the Appleton librarian. That's it.
Warren Cash(bank): Warren wants to take your money. I dunno why, but he does. Avoid if possible- he's a creep.
Flo Steamson: Flo owns Flowers by Flo. Good place to get wildflowers before going to Lava.
Henry Heimlich: Henry is the vet. He's in a couple quests.
Frank Tackle: Frank owns Out Fishing. He's a good guy- he gives out worms.
Goodwin Ryder: Goodwin's gear is not only tack but feed and clothes. It constantly has TSGs. I like this store a lot.
Inara: Inara is one of the beautiful NPCs. She's really nice and has a cute little tea table quest. definitely visit. Oh, and you play her a song.
Reuben. Ah, the creepy HI clown. He makes balloons and I think he's got a quest. Anyway-stay away if possible!
Faustus: I love him. He's a grumpy old man (which there are a lot of on HI) I hope he does get to go to Quiet Isle someday.
Elliot: Elliot is a brat. He steals a horse, among other things, and hides around the the meadow south of Faustus.
Adrianna owns WildFire, the genius horse. She loses him, and you find him, and leave him safe in the wild. Here is WildFire's location. 
Ursala: Ursala loves apples, and she has a cookie cutter.
Kaliska: Kaliska's house is full of heirlooms. She has a quest, I'm sure. Visit her- sweet old lady.
Sabella: Sabella is another apple lover, and she also loves the Appaloosa breed. She has a horse named Apples- the horse Elliot steals. Visit her!
Sumiko Stallman: Sumiko nobly dreams of opening a handicap riding stable. She has three hard quests- please visit her and help out a great cause :D
Ted Capocella: Ted is the racing steward. As I love to race, I love this NPC. He has some quick quests.
And now, here is Appleton:
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