I am going to be changing things up a lot from this point on, key story points will still happen but I'm going to have them happen in different ways as much as possible so the story isn't just a retelling with different characters.
Though Bilbo was in charge of the Ring, it was Thorin, Aragorn, Boromir and Legolas who made their travel plans. At first the younger ones had tried to join the group in deciding which route to take but it had descended into a shouting match they'd rather not be in the middle of. Bilbo and his brothers instead gathered their supplies, a simple task that turned out to be much more unpleasant than they'd thought.
"We're only going to eat this dry bread for months on end?" Fili exclaimed with horror while holding the leaf wrapped food, "We can't live off bread!"
"You can." The cook argued, "But if you find berries and game you are welcome to hunt it, but this is all I shall give you."
"But you've only given us a few dozen slices." Kili argued, "That would barely feed me!"
"I don't think this is normal bread, brother." Bilbo muttered, nibbling at it and feeling instantly satisfied.
"Lembas bread." The Elf corrected, "One bite is enough to fill the stomach of an Elven warrior for a day."
"I bet Bombur could eat all this and still feel hungry." Kili jibbed.
"I bet I could too." Fili replied.
The cook hit him over the head with her spoon.
-oOo-
"It's decided." Thorin announced that evening, "We will travel down through Mirkwood, past Dol Guldur and continue south to the Brown Lands."
"Sounds like a nice place." Fili noted dryly, Thorin gave him a look.
"We will follow the river for a while after that, but stop before reaching any settlements and instead head through the marshes, from there we will come to the Ash Mountains that surround Mordor."
"Mountains wont stop this Fellowship." Bilbo smiled, "Especially not with Dwarf members, we are the rulers of mountains!"
"Indeed." Thorin agreed, "But getting into Mordor will not be easy, once we get in getting to Mount Doom will be even more difficult, no doubt by that time the place will be crawling with Orks and Mahal knows what else."
Bilbo swallowed dryly and looked at his feet, he could hear the Ring trying to fill him with self doubt but he ignored it.
"We set off tomorrow." Thorin finished, "So get some rest."
Of course none of them took to their beds and instead they sat together in silence, all contemplating what this quest would be like. If anything, it was more perilous than there last. Bilbo remembered the night before they set out on their quest, all those years ago back in their small home in the Blue Mountains. He and his brothers had been awake all night, chattering excitably about slaying dragons and the glory it would bring.
They were no longer that naive.
A knock at the door broke the reverie.
"Excuse my interruption." Came the soft but commanding voice of Arwen, "I have come to give you these gifts to aid your journey."
She carried over a small bundle to their table and placed it town before turning back to them. The first item for each of them was an identical cloak, tailored to fit them, deep green with clasps shaped like leaves. Bilbo loved it immediately though he could see Thorin had some reservations about it.
"These cloaks help hide you from evil eyes." She explained with a soft smile, "They do not make you invisible, but they do help you blend in to your environment and warm your body."
"Thank you." Thorin said sincerely, Bilbo smiled.
Thorin would never fully trust Elves, but he knew when one was trying to act as a friend at least.
"These aren't half bad." Kili grinned, trying his on before realizing his words and going a little flustered.
"What I mean is- Uh..."
Arwen laughed and Bilbo rolled his eyes.
"Here." Arwen continued, holding out a length of silvery rope to the blushing Dwarf, "This Elven rope will never break and a single tug from it's owner will undo the tightest of knots. And for your elder brother, an Elven dagger, throw it in the air and when it lands on it's side the tip will always point north."
Bilbo count tell Kili was slightly affronted that he had been given glorified string while Fili a weapon but he knew better then to complain.
"For the King of Erebor," Arwen continued, "A scabbard to match his sword, should you ever lose the sword this sheath will fit any other you place in it and make it unbreakable and ever sharp."
Thorin nodded in thanks and looked genuinely pleased with the gift, of course he tried to control it but Bilbo could tell he was holding back a grin. No doubt he would be up the rest of the night examining it.
"Finally, Bilbo." The Elf smiled, though this time there was sadness in her smile.
She pitied him for his burden of the Ring.
Slowly she revealed a small phial from her pocket, for a moment it glowed brightly before dulling back to silvery water.
"This is the light of Earendil, the Elven star. When you need it most, it will light your way."
He clasped the small object in his palm, it was cool and some how soothing.
"Thank you." he whispered, some how he knew this would help him greatly.
"Father saw a chance for this evil thing to see its end many centuries ago." She explained, "We all want it gone for good this time."
"It will be." Thorin insisted, resting a hand on his son's shoulder, "We will make sure of it."
-oOo-
Despite the fact that it was his final night in a proper bed for what he assumed would be many months, Bilbo had not slept well. The Ring felt heavier every day and it felt especially so as he got ready to meet the rest of the Fellowship as the sun rose.
Fastening the leaf shaped cuffs together on his new cape he sighed, looking out over the edge of the balcony as the sun rose over the trees of Mirkwood. He could see the Lonely Mountain off in the distance to the east. Bombur would be awake by now, baking bread for his children's breakfast, Dwalin and Balin would probably be in the sparring ring. He suddenly found himself feeling very homesick.
Slowly he reached for the small pouch resting at the bottom of his pack and drew out the small object inside. A stone rabbit and the crystal ball containing Erebor. They gave him a small amount of comfort.
"Bilbo, it's time to go." Thorin called.
"I'm coming." He replied softly, quickly stowing the items away under his sleeping roll and food.
"Are you sure you want to do this?" Thorin asked seriously, "There must be somebody else who can carry that Ring without being corrupted, perhaps another Hobbit."
"I can do this." Bilbo replied stubbornly, "I found that Ring under Goblin Town for a reason. Destiny is a tricky thing."
Thorin nodded seriously.
"Come, the others are waiting."
And so the quest begins!