invokethehojo said:
2. Long-distance travel? I dont understand how a skill challenge could be built around that.
Have you
been to an American airport since around 2002?
Seriously, though, how about this:
"When we left off last session, you found out that Thorikan was heading to Archer's Gate to steal the Widget of Plot Derailment. He's got a head start on you of at least one day and Archer's Gate is 80 miles to the north, so... Skill Challenge! Tell me how you're going to travel the 80 miles and beat Thorikan to Archer's Gate."
It's somewhat pursuit-ish, but isn't exactly running someone down before they leave the city... it's about getting 80 miles from where you are now quickly (or making sure someone else doesn't.)
With failures, you get random encounters, your horse throws a shoe, the boat springs a leak, the wizard that knows the teleportation ritual decides it's not worth his time for the money you're offering, etc. With successes, you make progress and it looks like you're catching up to the bad guy. Succeed ultimately, and get there first, and more or less safely. Fail ultimately, and you find the grand wizard of Archer's Gate is a smoking corpse and Thorikan has run off with his Widget several hours ago.
Depending on what skills are used, it could be a test of negotiation (getting the wizard to cast the teleport ritual); a test of endurance and/or knowledge of terrain (Nature); a test of Arcana and Diplomacy, figuring out a way to magically signal ahead to the bandit camp in the forest near Archer's Gate, and making a deal with them to waylay Thorikan so he definitely won't get there first; or perhaps even a test of history, remembering that General Yowza of the Whatsitcalled Empire once had his advanced scouts reach Archer's Gate in less than a day by taming the wild Flying Frooza that live in the nearby woods. But it's still all about making travel plans and travelling.
Not sure if this is what the poster had in mind, but it's one option for a travel-oriented skill challenge.