Summary:
In the Appendix of the Lord of the Rings, Tolkien left a rather intriguing line.
2957-80 - Aragorn undertakes his great journeys and errantries.
As Thorongil he serves in disguise both Thengel of Rohan and Ecthelion II of Gondor. In SR 2957 (Shire Reckoning), Aragorn is 26 years old. He has been unleashed for several years now into the world outside of Rivendell, generally, and on the Northern Dunedain specifically. This story will follow Aragorn's journey, during his errantry, from the beginnings of his friendship with Gandalf the Grey till the end of his service to Rohan.

Author's note:
This is the first fan-fiction I'm writing. I intend to capture, somewhat, Aragorn's journey from the time he left his home in Eriador to serve with Thengel, till the time he returned home. I intend to break this into 2 or 3 stories, but since I'm not sure how long or how far this story will take me … we'll just have to wait and see.

This is book canon, first and foremost. Most information are gleaned from the Appendices and HoME. Since Tolkien has conveniently or inconveniently left this big hole in his story, most events are invented. I intend to extrapolate what was happening during this period of time from the events or comments elsewhere. Actually, this is also part of an exercise to theorise and rationalise the flow of events that finally led to the War of the Ring and the Return of the King. This is an exercise to find answers to some rather intriguing questions.

Why would Aragorn, a young 26-year-old man, leave Arnor and serve under men that he neither has obligation or allegiance? After all, as the Chieftain of the Northern Dunedain, his first duty is to his own people in the North. Did he come to Rohan by design or by accident? Did he come to Gondor to reconnoitre for his future plans to claim the throne? Can he be that cunning or sly at that age? How did Aragorn become the man that he is in the War of the Ring? 2957 to 2980! That's 23 years of growing up to do. How did seemingly unrelated people with individual motives seemed affect one another, the events around them and the future? How did they fit together?

I'll try to point out which are not canon, such as OCs; and sources or snippets of canon information, wherever relevant at the end of the chapter. If you notice any information I might have missed that should go in ... anywhere, please let me know. If you got some theories or thoughts related to this timeline and the proof to support them, I'd love to hear them.

Also, I intend to keep things as strictly canon as possible. These stories will cover mostly people one or two generations before the characters in the LOTR. I will not cover or write about ( fill in favourite character) if he/she was not yet born in the timeline or if Aragorn did not have anything to do with him/her coughLegolascough at that time.

I hope you will enjoy reading this and thank you.

1. First meeting

- Late autumn SR 2956 -

Estel wrapped his cloak tighter in the pre-dawn chill. It had been six years since Elrond had revealed his lineage to him. The euphoria and awkwardness of finding himself Chieftain of the Dunedain Rangers, the very men he had ridden with in his youth, had faded to easy acceptance. But he was glad that he had not been expected to take the mantle of his title and responsibilities immediately. For the time being, his uncle Lord Elemir remained as Acting Chieftain and his mother, Gilraen, was still the Regent of the North.

Estel stirred up the fire and returned to watch the road. Elladan and Elrohir were late. But he was not worried for Gildor's company had seen them outside Chetwood six days ago. Their mysterious guest must have been late.

When sky started to lighten, Estel saw only one horseman riding toward Weathertop. The rider was an old man with long grey beard, grey robe and a tall pointed hat. He carried a staff and strangely a sword of elven make.

"Estel of Rivendell. Well met," he said in Westron.

Estel froze in surprise. He was Strider to the outside world. Few knew his child name. And fewer still called him by that name now.

"Who are you? And why do you address by that name?"

"I am Gandalf. At your service." He bowed. "You are waiting for the sons of Elrond, are you not? How about a bit of breakfast while we exchange news?" With that, he made himself comfortable at Estel's campfire.

Feeling somewhat bested for the moment, Estel set about preparing breakfast for two. He set the kettle on the fire for tea and dugged out a pair roasted pheasants from the earth oven.

The stranger stretched himself warmly by the fire and pulled out a wooden pipe. Estel nearly burned his hands on the teakettle when Gandalf began blowing coloured smoke rings with obvious relish.

While Gandalf distracted Estel with his colourful smoke rings, he studied the young man carefully. The young man was attired in dark green cloak pinned with silver brooch shaped like a star. He must be one of the Rangers of the North. He noted the man's quiet ease and graceful efficient movements. And he was pleased. While Estel was a little wary, he was not unduly alarmed or fearful.

There were signs he had camped here for several days. A pile of firewood was stacked neatly in the corner of a shelter made from carefully lashed branches. And Gandalf had spied four birds in the earth oven. Obviously he was prepared for three extra guests. And the tantalising aroma hinted that he had taken time to collect herbs as well as to hunt.

"You have news?" asked Estel as he handed Gandalf his tea.

"Elladan and Elrohir have ridden back to Fornost." Gandalf passed a message pouch, sealed with a seven-rayed star to Estel. "We are to ride ahead to Rivendell. They will follow with your kinsman, Elemir."

Wordlessly, Estel broke the seal. Among the reports and letters, he found two addressed to his mother, one for Master Elrond and one to Strider. He opened the last one, recognising Elladan's sloppy penmanship.

Estel,
The messenger is Gandalf the Grey. He should carry a staff and Glamdring. You remember Adar spoke of Mithrandir before. He is known among the Eldar by that name. He has tidings regarding the Enemy. We will come fastest possible. Do not wait for us.
E & E

Estel stared thoughtfully at the letter. The twins had thought this important enough to involve the Dunedain and Gandalf trustworthy enough to carry dispatch.

"You have not answered my earlier question," said Estel sternly, though he sounded too uncertain to his own ears. "Why do you call me Estel?"

"That is your name, am I right? Elrodan said you'll answered to that name."

"Elrodan? How do you come by that name?"

"I seem to recall a small precocious child bestowing them that honour. Or have I made a terrible mistake? You are not Estel?"

"No. I am Estel, fortunately. May I see you sword?"

"This is Glamdring, once of Gondolin the Fair," said Gandalf in Sindarin.

"A fine sword indeed," he replied admiring the craftsmanship, satisfied Gandalf's credentials has been verified.

TBC...

Footnotes:

(1) 2956 - Aragorn meets Gandalf and their friendship begins.
Almost immediately after Aragorn befriends Gandalf, he left on his errantry. Theory : Gandalf is the catalyst that causes Aragorn to leave Eriador. Kind of like what he did to Bilbo, hmm? If not as directly as he did to Bilbo, at least indirectly.
(2) Have thought long and hard about what name Aragorn should think of himself. I've decided to settle for Estel for now, since it's only 6 years since Elrond revealed to him his true name and lineage. And you can't get rid of a habit (such as a familiar and well used name) that easily. Perhaps he will grow into the name Aragorn.
(3) Have decided to just introduce the usage of Strider, since there're no records of how or when he got this name. It may well be during his younger adolescent days, impatient and brisk.
(4) Did Gandalf know Strider is Aragorn or Estel? Was Gandalf aware of Aragorn's ancestry? He must have known the ancestry of the Chieftains of the Dunedain. Even if he knew, he may not know that Estel/Aragorn was any different for the generations of Rangers that worked with the Elves of Eriador.
(5) Fornost - Conjecture. HQ of the Arnorians or at least the Northern Rangers.

In 2957, the canon characters are :
Age - Name
26 - Aragorn, son of Arathorn
50 - Gilraen, daughter of Dirhael, mother of Aragorn
53 - Thengel, son of Fengel, King of Rohan
71 - Ecthelion, Steward of Gondor