I love the early stages of playing a character. You've got your whole career ahead of you. You need to work to get to the skill level and perks and gear that will complement your playstyle.

Maybe most importantly, everything is new - to that character. For the first, say, 15-20 levels, you discover locations for the first time. Travelling to Solitude or Riften or Markarth for that first time feels like an epic journey.

Unfortunately, and probably not coincidentally, it's right around level 20 that I begin to lose interest in my characters.

Once I've been to all of the cities and made a decent circuit of the province, the game begins to take on a back-and-forth tedium. Go here, kill this; come back, get rewarded. Etc. For the first several levels, that seems appropriate. The locations are new. But after awhile, you've been over the same damn stretch of road so many times. You've already *been* to Markarth a half dozen times. What used to be an adventurous trek of exploration has become a necessary evil, a stretch of dullness in between the 'action'.

How do you maintain an interest in your characters past this point?

I have tried only doing one quest at a time, but some of the questlines really force you to travel in nonsensical ways. I've tried staying in one area and 'clearing' the area before moving on. I dunno, I've tried several different things and it always seems that around lvl 20 I start to go, "Huh. Been here before. Time to reroll!"

For long distance travel I uses carriages, pay x coins to go to X-City then travel to destination. I use that instead of fast travel to try to keep RP aspect of it. I paid to get to a destination close to the area I need to get too.
Thats how I cut down on combat travel fatigue.
Bethesda should have cut out fast travel so people would use carriages more……..

I know exactly what you're talking about. I do a few things.

One, I try to linger in one area of the game world for as long as possible.

Two, I try to take a different route the second time, if one is available. I'll go way out of my way sometimes to find a route I haven't raveled in a while.

Three, I don't always play every day. When I've taken a break for a day or two or three traveling over that same stretch of road isn't quite as monotonous as if I'd done it just an hour ago. I have even stopped a play session on occasion when I'm faced with going back over a stretch of road. Tomorrow I'll be more ready to travel than now.

And four, I use carriages. A lot.

Try taking different routes (or go cross-country instead of following convenient roads), and use carriages between cities. This way exploring stays fresh, and you don't have to travel as much if you don't feel like it.