Complex sentence: The road "approximated" the Trace's route and was extended to Paoli, Indiana, after the state government leased operation of the road to a private organization as part of their negotiations to avoid bankruptcy.
Split into simpler sentences: The road "approximated" the Trace's route. It was extended to Paoli, Indiana, after the state government leased operation of the road to a private organization as part of their negotiations to avoid bankruptcy.