It all began because of his crappy fourth year. Someone who could be a good friend later was killed, and he had to deal with an information blackout because the Headmaster didn't believe him mature enough to handle any information.
So it was only natural that he see how long it took for the watchers to realize he left Durzkaban on his own two feet.
He had two legs and was used to walking, unlike a majority of magical people.
So he grabbed what he needed, threw it all in an expandable bag and enough food to last him a week and pretended to be on one of his usual walks around Surrey.
It took them an hour to realize he was long gone. By that time he was half-way to London because of a nice couple who gave him a lift.
"Has anyone been able to find him?" demanded Dumbledore.
"Not a trace. He's off the grid, and we found the remains of his wand in the room," said Moody.
It was clearly holly and the red and gold feather was visible to everyone there.
Sirius was the only one unconcerned. Trust his godson to go off the grid to make a point. Suddenly Arthur came rushing out of the floo.
"Umbridge has Harry. I overheard it from a contact in the Department of Mysteries...she's going to send him out of this world!" he panted.
Dumbledore ran to the floo and yelled "Ministry of Magic!"
But he would be too late.
"Well this is boring," commented Harry. He had been hijacked by some Ministry drone right outside London.
The pink toad who commanded the drones looked at him like he was a tasty fly.
"Look, can we get on with this?" said Harry bored out of his mind.
"So eager to die Potter?" sneered the toad.
"Actually I'm just bored. What's with all the runes anyway?" he commented.
"We're sending you far away, where no one will ever find you. That ought to teach you a lesson about slandering the Ministry," she said smugly.
"Really now? Think anyone would mind if I picked the destination? I mean if I really like it I won't come back even if my so called friends tried to bring me back," said Harry, finally interested in the proceedings.
"So the great Harry Potter would like to leave?" she said, eyes gleaming.
"The great Potter is sick of this nonsense and would like a long uninterrupted vacation," Harry corrected.
"Then by all means Potter, pick your destination! However if you ever set foot in Britain again be prepared for Azkaban!" sneered the toad.
"Fair enough," said Harry. He looked through the destinations and picked the one he liked best. It was in another dimension entirely, and it would be difficult to access twice without some serious help and Dumbledore levels of magic.
It was a clean world from what he could tell, remote and no real technology. Plus he could feel the magic from that place without having to step foot on it.
"Send me here and I won't bother you again, not unless some moron drags me back. But I will need a few things before I go, so I can properly enjoy my vacation," said Harry.
"Name them," said the toad. This was too good to be true! Potter was willingly leaving and guaranteed he wouldn't come back!
Harry made a quick list, though he would have to go to Diagon to get some of it. Not like he trusted these...flunkies...with his vault.
Harry walked out of Gringotts with nearly all his gold, every book in the family vault (among other things), and a brand new key for what was left of the gold.
He had transferred it to a new vault in order to keep the Ministry from getting their claws in it. And he put it under the name Yukiru Sugisaki.
(Yukiru Sugisaki is the creator of D.N. Angel.)
With how stupid the Death Eaters were, it was unlikely anyone would figure out that the vault had what was left of his gold. They wouldn't bother a 'foreign' vault, believing it to hold a paltry sum of gold.
He came out to find Hedwig looking rather cross with him.
"Sorry girl. Alright, let's get this over with," said Harry.
The toad smirked as they sent off Potter for good. Dumbledore tried to break into the ritual, but Harry was long gone. A gust of wind blew through the room when Dumbledore opened it, and sent all the papers on the subject and where Harry had gone flying. The runes had already vanished as soon as the magic took full effect.
Harry was long gone.
Harry woke up in the world he had picked. It was clean, much cleaner than home. The sky was clear, and there were pegasus flying...
Wait a minute!
Harry sorely missed his Firebolt as he wanted a better look at those pegasus. As he thought of flight, he felt something on his back making a whumping noise, much like a copter does when taking off.
Turning his head, he noticed that he now had midnight black wings! Wings that were apparently trying to take off it seemed. In shock, he grabbed his bag, only to discover that it had turned into some sort of saddlebag. A quick check revealed everything was still in it (except the Firebolt, which he could only assume had turned into wings).
He was about to go to the nearest lake to see what was really going on when he remembered something.
"Hedwig!"
A loud, amused hoot came from above. Apparently his owl had woken up before he did and had gotten past her own panic attack.
"Laugh it up Hedwig," growled Harry. She landed on his back (seeing as how her preferred perch of his arm was unavailable) as he went in search of a reflective surface.
Thirty minutes later...
"I don't believe it. I'm a bloody horse!" he said in disbelief.
His fur was a deep midnight black, and his mane appeared to have turned a deep blue with bright red streaks in it, but was as messy as ever. His tail was the same color, only the red had two tones instead of just one and it was straighter than his mane. He appeared to be a bit buff, but he was still in need of a growth spurt. His glasses, which were a broken black, had been fixed and turned an interesting shade of blue. His eyes seemed softer than before too.
His invisibility cloak had been altered too, which he hadn't noticed initially. And his trainers had been split into four and had changed into two different colors, dark blue in the front and magenta in the back.
Night had fallen while he searched for a lake of some sorts, and with it came the attention of the one who ruled it.
Harry was so exhausted from his travels he was almost about to fall asleep when a voice said behind him "The correct term is Pony."
He nearly jumped out of his skin...er, fur. He turned to find a beautiful night black mare with flowing mane that looked like the night sky above. On her flank was a small black splotch with a crescent moon. She had both wings and horn, and what appeared to be armor on her chest.
She also had this air that he had never seen before...almost regal in fact.
The thing that really got his attention was that she had some serious magic in her, because he could feel it and he wasn't even trying to!
"Now little stallion, who exactly are you? I can tell from the amount of magic around you that you don't belong here," she said.
Harry rubbed his hoof to his head.
"All I wanted was a normal vacation, and what do I get? Talking ponies..." he muttered.
"Most people don't jump dimensions looking for a vacation," she said dryly.
"They do if they were looking for some peace and quiet for a change. Back in my world people wouldn't leave me be, so when given a choice between being locked up or jumping worlds, I decided to leave my world and come to a destination that didn't look like it would get me killed," said Harry flatly.
"It couldn't have been that bad," she said.
"It was worse," said Harry.
"In any case, I needed to check who had arrived outside our dimension before they caused trouble."
"Oi! I don't cause trouble, it keeps finding me!" protested Harry.
The mare cocked her head when she heard the owl laughing at him.
"You swear not to cause any mischief in Equestria?" she asked.
"I may cause a few pranks here and there, but I won't deliberately cause trouble," said Harry.
"In that case, welcome to Equestria Mr.?"
"Call me Midnight."
"Welcome, Midnight. You may call me Princess Luna," said the mare.
Harry, now Midnight, did a bow.
"Word of warning... I would avoid my older sister Celestia if I were you. Last time someone traveled here outside our world, she didn't take it too well," said Luna before vanishing.
"Why does this always happen to me?" complained Midnight.
Hedwig merely hooted in amusement. Honestly, the things her nestling got into without trying!
Back in Britain...
"WHAT DO YOU MEAN HE ABANDONED US?!" shrieked Molly Weasly.
Everyone in the room winced.
"According to Umbridge's memories, Harry decided to leave our world willingly when informed of what the ritual did."
"What about his owl?"
"Confiscated by the Ministry and hasn't been seen," said Dumbledore. Hagrid had been most upset about that.
"His vault?"
"Emptied and closed," said Bill.
"His wand?"
"Snapped. Ollivander confirmed it, along with a rather sarcastic comment that he saw this coming when he realized how much we pushed the boy over the edge," said Dumbledore.
"What about his Firebolt? His Invisibility Cloak? His photo album?" demanded Molly.
"Taken along with the gold," said Dumbledore. They had checked for all of it.
"Any idea where he went?"
"All the papers with any hints of runes and the ritual circle itself are gone. Summoning charms won't work on it."
This only encourages Hermione, who dives deep into old books to find the ritual to locate Harry and another to bring him home.
Midnight was in such a good mood. Ever since ditching his world he had been free to do as he pleased. Strangely enough, his galleons and other currency immediately converted to bits, the dominant currency of Equestria. He wasn't complaining, but he did think it a bit odd.
Hedwig absolutely loved Equestria, because the air was so clean. Eventually Midnight ended up in a small town called Ponyville.
Midnight's first stop was the library to see what sort of selection they had. After two months of living in Equestria, he was delighted to learn that he could channel his magic through his wings since he had been turned into a Pegasus instead of a Unicorn.
"I'll be down in a moment!" yelled a female's voice.
A young unicorn about his age with a bright pink and white cutie mark that looked like a group of stars came down from the upstairs. Behind her was a light purple baby dragon with green frills. Oddly enough they shared the same eye color.
"Welcome to the Ponyville library. What are you looking for?"
"Nothing in particular, just looking around," replied Midnight.
"Are you by any chance new in town? I've never seen you around here before," asked the mare.
"Just came to town actually. I've been wandering around Equestria for a while now," said Midnight.
"I'm surprised Pinkie didn't see you. She likes to great the newcomers," said the dragon.
Yet another thing he had gotten used to. Several animals could talk here, with the exception of the much smaller ones. The first time he heard a Diamond Dog talk he had nearly freaked out.
"What's your name?" asked Midnight curiously. It was rare to meet a friendly dragon.
"I'm Spike!"
"My name is Twilight Sparkle," said the mare.
"Midnight Cloudrunner, and this is Hedwig."
The snowy owl hooted once before going back to sleep. Sitting on her nestling's back while he was walking was very soothing.
"So what brings you to Ponyville?"
"Finally left school, my parents left me a sizable amount of bits, and I really didn't want to settle down so I went on a walk one day and haven't stopped yet. I generally stick around for a few weeks and move on. Coincidentally do you know of anyplace I could stay for a few weeks? Clouds are nice and all but it's not much fun when it rains," said Midnight pleasantly.
"You might want to ask Applejack over at Sweet Apple Acres, or if you can handle animals Fluttershy might be able to help. However if you value your sanity avoid Cupcake Corner, because Pinkie will talk your ears off. Rarity might use you as a dress-up doll if you stayed with her and Rainbow values her privacy," said Twilight bluntly.
"Thanks. So what sort of selection they have around here?" asked Midnight.
Being around Hermione for four years had nearly killed his natural love of libraries, but being in an entirely new world without the bossy bookworm had miraculously revived it.
As Twilight took him through the various sections, Midnight noticed with amusement that Spike was watching him like a hawk. Apparently the fact someone had asked him for his name first instead of Twilight had impressed him or something.
So it came as little surprise that Twilight had Spike lead him around Ponyville.
Midnight was beyond amused by Spike and his infatuation of Rarity. The mare was an overplayed 'Lady' which amused him to no end, unlike how Ginny occasionally acted whenever she believed him to be out of range of hearing or sight.
He knew everyone and their grandmother believed he would fall for Ginny and have a smattering of ginger and black haired children, but to be honest he had never seen the girl that way.
Not to mention he loathed all fangirls with a passion, and Ginny still acted like one.
True to Twilight's warning, the second Rarity saw his coloring and coat she dragged him into her workshop and insisted on giving him a new outfit to wear.
Midnight didn't mind, because honestly the only clothing he had was his cloak and his by now worn out trainers. He liked walking and while flying was fun, it grew tiring rather quickly as he had yet to build up his flight muscles.
Because of Princess Luna's warning, he didn't want to stand out by not being able to fly for longer than an hour (even less at his top speeds) unlike most of the Pegasus ponies he saw around.
About the most flying he had done since coming here was to get to a nice cloud above the ground to nap, and even then it was a total pain sleeping on the ones that rained.
And don't get him started on the thundering ones...
It would be three hours before he managed to escape Rarity, to the amusement of one baby dragon and snow owl. And nothing would be said of the matter later.