From Staunton to Harrisonburg, the primary connections to Richmond went through Swift Run Gap and Rockfish Gap in the Blue Ridge. The "mountain road" (now US Route 33) crossed at Swift Run Gap. The "Three Chopt Road" (still called the same in West End Richmond) was marked originally with - surprise! - three notches on trees, to identify the colonial era path through the woods from the Blue Ridge to the falls at Richmond. (Originally, Three Chopt Road crossed the Blue Ridge at Browns Gap, slightly north of Rockfish Gap.)
The James River and Kanawha Canal, built in the first half of the 1800's, became the primary transportation corridor between Richmond and Lexington. The canal carried cargo and people on relatively fast trips along the river - and in 1863, Stonewall Jackson's body was returned via a canal boat to Lexington for burial. Further north, in the lower Shenandoah Valley, the Manassas Gap Railroad carried products to Alexandria.
One city is missing from this story of transportation from the Shenandoah Valley - Fredericksburg, the major Fall Line city between Alexandria and Richmond. Fredericksburg never established an effective transportation corridor to become a market city for the Valley - or even the Piedmont, after failing to build a canal system up the Rappahannock River.
Look at a highway map of Virginia today, and you'll see just US Route 17 connecting Fredericksburg directly with the Valley. It crosses the Blue Ridge at Ashby Gap - and the Alexandria merchants intercepted the Valley trade there with their first turnpike. For the last 150 years, most trade and travelers from the middle of the Shenandoah Valley have followed the Little River Turnpike (now US Route 236/50) or used the railroad built through Manassas Gap to reach Alexandria. That's why, today, there's no railroad and no interstate highway leading west of Fredericksburg - in contrast to I-64 leading west of Richmond and I-66 leading west of Alexandria.
This pattern of transportation shaped the economic and political connections of the Valley and of
Fredericksburg. The Congressional District boundaries of today still show the effects of the transportation
investments made prior to the Civil War. The Tenth
Congressional District stretches from the edge of Arlington County to West Virginia now, but other Districts are split by the Blue Ridge - except for Page County, which is in the same Seventh Congressional District as the western suburbs of Richmond.
The boundaries for State Senate districts for General Assembly elections show the importance of the Blue Ridge - though the northern part of the valley is politically connected to the Piedmont in District 26 and District 27: