So, with the above in our minds, we're currently working on a way to resolve the design issue.
We have a couple of ideas and we're still deciding on the final implementation.
The two main ideas we are considering are:
Being able to get a "caravan" from the area just outside the outskirts, which takes you to the area in the middle between Tilverton and Arabel. You can then continue on foot, and get a separate caravan after traversing the rest of the area.
This would mean you have to travel 2 areas on foot (which bandits have access to), and utilises assets already in place - it does mean we'd have to consider various things in those areas however, and couldn't add anything "unique" as such, to the travel.
Being able to take the trade route (hitch on a caravan) - You would arrive in one of two new areas (which bandits could also enter) after having gotten off the caravan. You must then traverse those areas, and at the end come out close to your final destination. This allows unique things to be done in these trade route areas. Does not interfere with current areas, but does require creating new assets.
Both ideas should work, and would allow the choice of a player to either take the long road, and go adventuring in the areas between the two locations, or, take the fast route to simply travel between the two.