I seemd to recall a while back that you could plan a (road) tirp with multiple points in it. (ie. Orlando > Atlanta > Richmond > NY > Chicago) but I can't seem to find that now it's just point A > B.

Do they no longer do this? Was I thinking of another site?

No, you're right. Mapquest used to offer the option of planning roadtrips on their site, along with the option to select various routes depending on whether or not you wanted to avoid interstates and highways but apparently both of these options are now gone. If you want to plan a road trip, I recommend Roadtrip Planner

I recommend not using shitass Mapquest.

Use RandMcNally.com

I stopped using MapQuest after they got me lost for about the 5th time. When you want a map, use someone who has years of experience actually making them.

MapQuest got me lost more than once - they often tell you to get off at an exit number for a road that does not exist, or neglect to mention exit numbers at all. Yeah, like I want to be stuck in Newark's "Killing Fields"

I use my big ol' road atlas that my insurance company sends me for macronavigation, and get directions for the local areas once I get off the interstate from the people at the place I'm going to.

GPS is really sweet. Just enter your destination and hit the gas.