Eregion. Winter T.A. 3011-3012. Jack leaves the beaten path for the first time, all alone. The last time he did so he followed the tracks left behind by his Companions, travelling from cache to cache where they had left firewood, kindling, and small foods. He soon learns that the harsh wilderness of Eregion is less bountiful, and after only a few days of battling uncleared paths full of weeds, brambles, holly and thistles, he is bloodied, thirsty, hungry and alone. He is afraid of eating from the many growths, remembering Feredir’s stern warnings about deadly fruits and berries, and restricts himself to those plants he knows without doubt. Those are few. He attempts to put up snares, but finds that it is not as easy as his Companions have made it seem – nor is kindling a simple trick, and he is soon down to his last, few matches, keeping them religiously safeguarded in a waterproof pouch about his neck. In addition, he has the nagging feeling that he is being watched, which makes him walk in a constant state of fear. Any small sound is enough to make him jump. And there are many.
One night, when drizzle has ruined his chances of a warm fire, and he is huddled and shivering under a thicket, he feels a presence in the undergrowth. There is something there! Something approaches, and he is elated to realize that it is Feredir’s wolf, Grey Cloak, that is stalking him. Then that elation turns to terror, as the giant wolf bares its fangs, and leaps straight for Jack, who falls to the ground with a wail of terror! There is a terrible sound, and Jack carefully takes his hands from his face, to see the wolf stand victorious over another wolf – a wolf that was about to attack Jack from behind! Grey Cloak has saved him!
As the days pass, Grey Cloak never leaves Jack’s side, keeping him warm at night, and offering his solid frame for support when the Hobbit falters. Grey Cloak is large enough that Jack could ride him, but the wolf doesn’t seem comfortable with it, so Jack doesn’t push it. Some times the wolf will disappear and return with some small game that he shares with Jack, who most of the time simply eats it raw to avoid starvation.
Then one day, Jack is unable to get up. His now very close companion Grey Cloak whines and nudges him with his muzzle, but Jack is too weakened by hunger and fatigue, sickness has taken him over. He has no concept of how long he has lain like this, but at some point he registers faint voices, sees flickering figures about him. Gradually he quickens, under the care of a group of Elves – a Wandering Company. Initially, Jack tries to refuse their help; it goes against his Path of Redemption to accept their help. Unfazed, the Elves withdraw. But the folllowing days, Jack notices that whatever direction he chooses, the Elves seem to have chosen that path before him. They leave small things for him; foods, drink, garments, that he initially refuses, but then grudgingly accepts when he comes across them again the next day. He starts seeing them in the distance, and soon he follows closely enough to watch their motions. He sees that they spend a good portion of every day meditating or doing excersises that seem similar to the katas Jack has learned as a martial artist. Within long he is doing these with them, first at a distance, but as the days grow colder Jack trains and meditates alongside his new friends. They do not speak much – the Elves do not speak Westron and Jack is no wizard at Elvish – but they make themselves understood. They help him reach deep inside himself in meditative techniques and they teach him the fundaments of bushcraft. Jack is starting to feel much better, both in body and in spirit: these Elves have helped him reach a new level of enlightenment. Then one day when he wakes up, the Elves are gone. There are no tracks, no signs of them ever having been there. Were they ever there? Jack considers his new clothes and equipment – proof that the were, but at the same time he can’t shake the feeling that it all happened not in the real world, but in a dream-state. While packing his sack he finds a set of beautiful bracers, clearly of Elvish design and a perfect fit for Jack. Renewed, fortified, and slightly more elfin-looking, Jack Fleetfoot returns to the woods with his friend Grey Cloak, and does not re-emerge from the wilderness until the mountains have thawed and spring is in full force.