I want the players to start engaging with an under-explored area. The premise is that a piece of land, about the size of Connecticut, was held by various orc tribes for the last hundred years. Sentient humanoids have lived in the area for four millennia, but all contact with the towns and holds in the area were lost during the orc Waagh. Recently, reports of orcs have subsided, and the land is rife to be explored by risk-taking people, namely the PCs.

I plan to have a session zero involving discussing the setting, expectations and style of play, the practicalities of exploring the area (and returning to home for rest), and of course making characters.

But how do I get the players started so that they are both pushed in the right direction and get used to making their own decisions? I was thinking of having a merchant pay them to map an abandoned road to the next town and help him make it safe for travel - that mission alone could take a 6-8 hours of game time to complete.