My favorite place to skate is the Huckleberry Trail in Blacksburg, Virginia. The trail starts in Blacksburg near the library, winds past the stadium through VT farms and the woods, and ends at the mall in Christiansburg, six miles total. The pavement (mostly asphalt) is good quality. The first three miles have big hills that make for a challenging skate. There are a few boardwalk bridges.
http://www.montva.com/departments/parks/htmap.php
