The Pioneer Hexcrawl

This is probably going to be the most familiar part of the entire pioneer endeavor, and that presents a unique challenge.  This hexcrawl has to be different than any other hexcrawl you have ever run.  Even if your players have traveled extensive distances with wagons and gear, this will be an entirely new hexcrawl for both them and you.  This hexcrawl is responsible for setting the tone of the entire settlement adventure, introducing your players to a different way of thinking, one much more grounded in the physical reality of their characters' situation.

We'll start at the beginning: preparing for the journey.  The full traveling group should number at least 20, including player characters: if the players want to do more than build and operate a single farm, they'll need more bodies.  The more hands on deck at the end of their journey, the easier constructing the settlement will be (remember that video last post of the approx. 50 workers raising a barn in 10 hours?).  Also, some of the non-adventurers will die along the way.  That will be a consequence of the journey.

The group's makeup will factor hugely into the success or failure of the venture, with regard to both the overall skillset and the relationships between each individual member.  I'll devote a post just to talking about the expeditionary group, which is why I'm going light on the details here.

Once the group has been created, the party needs to acquire supplies.  While I love fiddling with spreadsheets and accounting and looking at all of the fiddly details, I recognize that not everyone finds it fun.  Tough.  While you, the DM, absolutely must help the party choose supplies and quantities (offering suggestions and observations frequently), when the party makes all of the final decisions, they assume the responsibility for all of their equipment.  When a crucial supply is necessary and they didn't buy it (or didn't buy enough of them), they can only get angry with themselves, as opposed to blaming whatever abstraction is used so that your players didn't have to sit through and approve every blessed item.

As a rule of thumb, the group needs enough wagons that everyone in the expedition and all of the equipment can fit into the wagons.  Give each wagon a name and character sheet and distribute them to the players.  Wagons will have hit points and take damage from terrain hazards.  When they lose all of their hit points, they break - either the wagon tongue snaps, a wheel breaks or (eesh) an axle cracks (determine this randomly, say on a 1d6, 1-3 break a wheel, 4-5 wagon tongue, and 6 break the axle).  Repairs take a half-day, assuming appropriate replacement parts are on hand.  Unlike a regular injury, determine the next kind of break the day after the first one has been repaired - so if a wagon busted a wheel yesterday and was fixed, today the DM would determine what would break next - as the expedition travels, people will keep an eye on the wagons and will notice that the axle has developed a small crack, which is fine right now, but a couple big jolts will splinter it.

Every item brought on the expedition needs to have some condition for it to not perform as expected or needed - tools need a breakage chance, stored food needs conditions under which it will spoil, etc.  These odds should be slight and conditions unlikely - but they need to be explicitly stated and recorded somewhere.

You will need foraging rules - if a full day is spent foraging, how much food can be brought back per forager?  They'll need to account for vegetation and foraging skill.  I have a Hunter skill: it is an Apprentice task to find food for 1 in the woods.  Plains and scrubland are a Journeyman task, and desert and similarly inhospitable terrain require a Specialist Hunter test, and the difference between the check result and the test's difficulty (minimum 1) is the number of people that can be fed on a successful roll.

Lastly, in addition to the normal encounters of your hex crawl (random encounters, interesting location-based encounters to keep things different and interesting for your players), you will need journey hazards that put stress upon the wagons, equipment, and expeditionary group.  Things like needing to clear a path through a forest, crossing a river, a rockslide coming towards the wagon train or a mudslide that has washed away the path.  I'm a big fan of a 1d6 encounter die for most wilderness encounters, with a check every day.  Here, I'd roll 2d6 - one to determine whether an encounter occurs or not, the other to determine the type: 1-3 for a typical hexcrawl encounter, 4-5 a travel hazard, and 6 an interpersonal conflict within the expeditionary group.

So: takeaways from this brainstorm.  The Hexcrawl section requires:

Wagon character sheets

Expeditionary group mechanics to randomly create clusters of people interested in joining the party's caravan and simulate their interpersonal relationships

Thorough equipment lists, detailing dimensions, components, break or spoilage conditions, etc.

Hexcrawl encounters including typical hexcrawl items (wandering monsters, lairs, ruins, etc.), travel hazards, and interpersonal conflicts

That's a start.