This tutorial video features the Record History Tool and Grasshopper to sketch roads.
The Record History Tool is located in the bottom toolbar of Rhino. Toggling on Record History will save the next command and it’s effect on the source geometry used by the command. Record History is particularly useful for situations in which geometry needs to be re-drawn when the source geometry changes (i.e. massing, roads, etc.) A full list of all the commands that Record History can store can be found at http://docs.mcneel.com/rhino/5/help/en-us/commands/history.htm
Grasshopper is particularly useful for sketching roads because it lets us continuously build-out the definition if we want to have more than the road outline. Note that Grasshopper comes pre-installed with Rhino 6 but not with Rhino 5.