Road trip blues

So Well of Midnight, a MLP fanfiction is going to be a road trip story set on Earth.
Well, except most of the folks living there have been swept away by the Black Cloud.

What's left?
Two or three, Nightbringers, major servants of the Well of Midnight.
One Heirophant, teacher of Well magic.

A whole bunch of humans that want to create a purple America.
And the Resistance that fights the purple Americans.

Finally, Matt Varney and his road trip friends.
Calvin- An ex military guy, Matt helps.
Felicia Dawn- A changeling who is helping Matt because she wants revenge on the purple Americans who attacked her home, and killed her brother and friends.

Zoland from Zeryphesh- A gunslinging zebra from another pony world.

My problem is coming up with events that fit the four stops Matt and friends make before the final one at the copper mine in Wyoming.
Now, I'm sorta gearing up for the trip. They managed to survive fighting well creatures in a small town in Georgia.

Here's the list of places in the story.
Some of the names have been tweaked so I don't piss off the residents.
Used google maps to get the names.

Levansville, Tennessee
Marack's Creek, Missouri
Mirna, Nebraska
Syodark, Wyoming

Left out Ryrdal, Georgia, because that's done.

So what's out there?

The remaining Nightbringers probably have their own projects.
Well creatures probably have taken over some towns for their own amusement.
Purple Americans are probably planning to crush all resistance.
Then you have the Resistance fighting the Purple Americans.
Matt Varney has to learn and accept his purity powers or he will fail at the end.

I know how the story will end, and the beginning has already been written, but the middle is a big blank.
Probably have to go back and do more world building.

Even though I've read some great road trip stories, I don't know how to write one myself.
I'll probably post a thread on Fimfiction about it.