Joe,
We stay in the Penn Hills area the first night on the way to Carlisle. Its about 3/4 the way. We stay at nice Marriott hotel. Good restaurant area & safe area for Speedster. Makes a nice easy 3 hour drive the second day so you're not tired for the Thursday activities. It would be cool to caravan. The first day is a biotch(hopefully construction done on turnpike) but the second day is an awesome drive through the hills and down into Carlisle.