He decides to stop at The Frozen Hearth*, first, to get some food that'll last longer than what he can get at the College. The banquets there are all very nice but they're not optimised for being carried in a bag and remaining edible over several weeks. The inn, serving as a place travellers stop at, is much more likely to be able to supply him thus.

He considers summoning an Ethereal Horse for the trek there—the inn is right by the main gate of the city, so a fair walk away from the College—but decides to walk. He has twenty Scrolls, which should cover the whole trip to the little mining village of Stonehills and back, depending on the path he takes, and he shouldn't be wasting them on short trips.

If he only follows main roads, it should take approximately ten to twelve days to get there: south towards Windhelm, then West into the Pale and north towards Dawnstar then back west and south into Hjaalmarch. That'd be cutting it close, and assuming he doesn't learn the spell by then he'll be in a bit of a bind. If he cuts through Winterhold proper directly west then south it should be about a week. A more dangerous proposition, but with an ethereal steed it should hopefully not be much of a problem; the horse won't get tired or hurt, and it can probably outrun any threats.

Map of the Trip

That decided, he grabs the Spell Tome on Conjure Ethereal Horse and starts to read, trusting his feet to carry him through the now-familiar streets of Winterhold to the inn.

(* The Winterhold inn, where Ruby was first taken to after passing out by the gates of the city.)

The spell isn't that difficult. He'll need to study it for a while, but not that long a while; it's basically a modification to the Conjure Familiar spell—which by default summons a dog—to instead summon a horse. There are a few other differences, such as the fact that the horse doesn't need to be as resilient but needs to be faster, or that its behaviour should be biased towards not engaging in combat where the original spell summons a very protective spirit, but the kernel of it is the same.

Ruby almost walks past the entrance to The Frozen Hearth, so distracted is he by the book, but when he notices he's walking through the gate he turns on his heels and makes a beeline to the inn.

"Evening, Nelacar. Evening, Enthir. Evening, Dagur." The two mages are at a table together; Enthir ignores Ruby, but Nelacar smiles at him and lifts a mug filled with mead as way of greeting.

    "Evening, Ruby," says the innkeep. "You're having the usual?"

"Yes, please, though I'm going on a little quest so I'll also be having whatever you have that can keep for a few weeks."

    "Can do. Make yourself comfortable."

So he walks to his usual table, puts his bags down, takes a seat, and resumes reading the book.

Dagur brings Ruby his food and his mulled wine in short order, and he decides he'll just spend the night here and leave in the morning. He could probably have stayed in the College, but what can he say, he got excited by the prospect of a quest and forgot to check the time.

When he's done with his supper and into his second cup of wine someone pulls the chair across the table from him and unceremoniously drops themself onto it. Ruby looks up from his book with a raised eyebrow and says, "Can I help you?"

"Maybe!" says the human woman, grinning at Ruby, eyes slightly glazed over in a way that looks... not not inebriated. "M'name is Sam. Sam Guevenne."

"Ruby. A pleasure to meet you." He puts his book down and focuses more fully on Sam.

"I'm lookin' to have some fun. Are you fun, Ruby?"

"I am."

"I thought so. You looked fun."

"What kind of fun are we talking about, here, then?"

"I wanna make a bet. I bet I can drink you under the table."

"You know, for some reason I thought you were flirting with me."

"I am. If you win the bet..." She looks around then leans forward conspiratorially. "You get one kiss."

"Ah huh. And if you win?"

"I get one kiss!"

She's clearly incredibly drunk, but she's kind of endearing.

"I think that's not that good a bet, you see, because if one of us is under the table then kissing becomes a lot harder."

She spends a while considering this, her eyebrows furrowing deeply.

"Fine. No bet. Let's just get drunk and make out."

Ruby laughs. "Sure, why not? Hey, Dagur! Give us some strong Nord mead."

    "On the way."

He's already decided he's staying the night here, might as well have some fun with a cute girl while he does it.

Dagur brings them a whole flagon, and Sam immediately fills her mug and downs it all.

"You're a mage," she observes.

Not wanting to be outdone, Ruby downs his own mug as well.

"What gave me away?"

"You're—" She hiccups and clears her throat. "'Scuse me. You're naked."

Ruby tugs on the hood resting around his shoulder. "Not naked."

"Fine, you's got a bunch of stuff on your skin that's like clothes and your cock's still out." Hiccup. "Nice cock, by the by."

"Thank you," he says, laughing again. "Alright, you caught me, I'm a mage."

She fills her mug with more mead then asks Dagur for more.

"Zzit true? That mages are all..." And she makes a rude gesture with her hands, index finger of one hand going into a ring formed by the index finger and thumb of the other. "Pervs?"

"From what I can tell, kind of!" Sure, more mead. "No nudity taboo, no sexuality taboo to speak of, people do kinda fuck each other all the time like it's nothing."