no railroad was built before the Civil War to connect the Winchester and Potomac Railroad (blue) with the Manassas Gap Railroad (red)
Source: Library of Congress, Map of the Manassas Gap Railroad and its extensions (1855)
The Winchester and Strasburg Railroad built track in 1870 that finally closed a gap between the two towns. The new railroad was controlled by the Baltimore and Ohio Railroad, which planned to extend its system up the Shenandoah Valley and all the way to Salem.
The Winchester and Potomac Railroad had connected Winchester with Harpers Ferry in 1836. When the bridge across the Potomac River was completed a year later, the combination of those railroads improved transportation dramatically between the northern end of the Shenandoah Valley and the port city of Baltimore. The charter of the Winchester and Potomac Railroad did not authorize construction south of Winchester.
The Manassas Gap Railroad reached Strasburg in 1854. From there it turned south. The charter did not authorize construction of track north of Strasburg towards Winchester.
Track of the Manassas Gap Railroad reached Mount Jackson before the Civil War, but construction was not yet completed to the planned endpoint at Harrisonburg when war interrupted construction.
the Manassas Gap Railroad was completed only to Mount Jackson prior to the start of the Civil War
Source: Library of Congress, Upper Potomac from McCoy's Ferry to Conrad's Ferry and adjacent portions of Maryland and Virginia
The Manassas Gap railroad provided faster, cheaper transportation to the port city of Alexandria for those living near its route in the Shenandoah Valley. However, the farmers located between the Manassas Gap Railroad at Strasburg and the Winchester and Potomac Railroad in Winchester still lacked easy access to rail transport.
The farmers between the Manassas Gap Railroad in Mount Jackson and the Virginia Central Railroad in Staunton were equally unserved. They were obliged to cart their crops, by wagon on the Valley Turnpike, to reach a railroad station from which they could ship to Baltimore or Alexandria.
Between 1836 and the Civil War, all canals and railroads in Virginia were designed to connect the Piedmont and Shenanoah Valley to just four locations - Alexandria, Richmond, Petersburg, or Portsmouth/Norfolk. Merchants in Alexandria used their clout to prevent the Virginia legislature from allowing the Winchester and Potomac Railroad to extend further south; that would divert business to Baltimore. Farmers and iron furnaces in a substantial portion of the Shenandoah Valley were forced to haul their products by wagon to one of the railroad stations, or float their freight by boat to Harpers Ferry.
In 1861, Col. Thomas Jackson traveled from the Virginia Military Institute to Harpers Ferry. He led cadets to Staunton, where they caught the Virginia Central trains to get to Richmond. On his way north by train from Richmond, he sent a message via telegraph on April 29, 1861 to Governor Letcher of Virginia encouraging him to build a rail link closing the 18-mile gap between Strasburg-Winchester "for strategic purposes."
at the start of the Civil War in 1861, the rail connection between Winchester and Strasburg was envisioned but not chartered
Source: Library of Virginia, A map of the rail roads of Virginia
On June 19, the Virginia State Convention endorsed the idea. That convention had been elected to consider whether Virginia should secede from the Union. After two months of debate, it passed the Ordinance of Secession, and voters ratified it on May 23. The "Secession Convention" reconvened in June, without members from the western counties who had returned home to prepare to split off and form a new state. It passedby 54-36 a motion declaring:1
"An ordinance providing for the speedy completion of Rail Road Connections between Richmond and Harpers Ferry," Acts of the General Assembly of the State of Virginia, William F. Ritchie, 1861, p.49-50, https://books.google.com/books?id=fvFQAQAAMAAJ (last checked July 25, 2020)
The only rail link to Harpers Ferry was the B&O through Baltimore. Virginia/Confederate troops would be slow to support military operations at Harpers Ferry, because they had to march by foot along the Valley Pike from Strasburg or across a gap in the Blue Ridge further north. However, Confederates evacuated Harpers Ferry in July, 1861.
That August they began removing locomotives and rail cars. The equipment was hauled south to the Manassas Gap Railroad at Strasburg, then transported to Richmond. Starting in October, they stripped enough rails from the Baltimore and Ohio Railroad to build over 36 miles of track. Where the B&O was double-tracked, rails were removed from one line and loaded on a train on the other track. Horses then pulled wagonloads of stolen rail on the Valley Turnpike between Martinsburg and Strasburg.
Thomas Sharp, who led the removal project, recommended using the rails to build the track needed to close the Winchester-Strasburg gap.1
Edward B. Burns, "The Confederates Gather Steam," The Railway and Locomotive Historical Society Bulletin, Number 104 (April 1961), p.8, p.23, https://www.jstor.org/stable/43517986; "Virginia State Convention, Fifth day - Second session," Richmond Dispatch, June 19, 1861, https://dispatch.richmond.edu/view/secondary-section-view.php?doc=D_019_139 (last checked June 15, 2020)
Col. Daniel McCallum, the Union military official in charge of the US Military Railroad, made the same recommendation in 1862 when Federal forces contolled the northern part of the Shenandoaf Valley. Within a month he had estimated the cost for a Winchestr-Strasburg link, but no track was built between those two towns until after the Civil War. During the conflict, Winchester was a center of conflict and changed hands about 72 times; no railroad construction was possible.1
Charles E. Fisher, "The U. S. Military Railroads," The Railway and Locomotive Historical Society Bulletin, Number 59 (October, 1942), p.55, https://www.jstor.org/stable/43519806; "Civil War History," Discover Winchester, https://visitwinchesterva.com/civil-war-history/; Daniel C. McCallum, "United States Military Railroads Report," Government Printing Office, 1866, p.6, https://openlibrary.org/books/OL24992627M/Reports_of_Bvt._Brig._Gen._D._C._McCallum_Director_and_General_Manager_of_the_Military_Railroads_of_ (last checked April 10, 2020)
After the Civil War, the General Assembly was more willing to charter new railroads that would attract northern investors and revitalize the state's devastated economy; the Manassas Gap Railroad could no longer block competition. The Winchester and Strasburg Railroad received authorization to build between those two towns in April, 1867, and officially organized in 1868.
"Winchester and Strasburg Railroad Company," Annual Report, Virginia, Railroad Commissioner, 1898, p.487, https://books.google.com/books?id=mCUaAQAAIAAJ (last checked June 2, 2020)
The Manassas Gap Railroad did manage to get a provision added to the charter of the Winchester and Strasburg Railroad, giving it first rights to build the track needed to close the 19-mile gap. The Manassas Gap Railroad was unable to obtain the financing required to build new track north from Strasburg to Winchester; it ended up having to merge with the Orange and Alexandria Railroad in 1867 to create the Orange, Alexandria, and Manassas Railroad. It completed track south to Harrisonburg at the end of 1868, laying rails on the roadbed which had been graded before the Civil War. In 1869,
The Baltimore and Ohio (B&O) Railroad financed the construction of the Winchester and Strasburg Railroad. In 1870, once the track was completed, the Baltimore and Ohio Railroad officially took control by leasing it.
The B&O also obtained control in 1872 of the Orange, Alexandria, and Manassas Railroad and renamed it the Washington City, Virginia Midland, and Great Southern Railroad Company. In 1873 it arranged a lease of the track between Strasburg and Harrisonburg, creating what became known as the Strasburg and Harrisonburg Railroad.
The Winchester and Potomac Railroad, the Winchester and Strasburg Railroad, and the Strasburg and Harrisonburg Railroad/Washington City, Virginia Midland, and Great Southern Railroad Company were controlled by the Baltimore and Ohio Railroad and known as its "Valley Line." Using its earnings and borrowing power to obtain capital from Northern capitalists, the B&O acquired and built track in hopes of creating a new mainline west of the Blue Ridge. That would allow the port city of Baltimore to benefit from traffic coming from North Carolina, Tennessee, and Georgia.1
"Reconstruction, the Railroad and a Name Change, 1866-1899," Newtown History Center, https://newtownhistorycenter.org/town-history/reconstruction-the-railroad-and-a-name-change-1866-1899/; J. Randolph Kean, "The Development of the 'Valley Line' of the Baltimore and Ohio Railroad," The Virginia Magazine of History and Biography, Volume 60, Number 4 (October, 1952), pp.545-547, https://www.jstor.org/stable/4245875 (last checked April 14, 2020)
The B&O continued building its network south from Harrisonburg, using the Valley Railroad. It reached Staunton in 1874 and Lexington in 1883. However, the B&O was unable to fund construction further south to Salem and into North Carolina or Tennessee as envisioned. In 1882 the rival Shenandoah Valley Railroad connnected with the Atlantic, Mississippi and Ohio Railroad at a junction which developed as Roanoke, and those two railroads were combined to create the Norfolk and Western Railroad.
Traffic across the Winchester and Strasburg Railroad, as part of the Baltimore and Ohio Railroad system which ended in Lexington, never matched the coal and freight traffic on the through-line of the Norfolk and Western Railroad just 10 miles to the east.
The Baltimore and Ohio Railroad was financially overextended when an economic recession in 1893 reduced revenues. After going into bankruptcy, the B&O lost control of the Washington City, Virginia Midland, and Great Southern Railroad Company and its track south of Strasburg in 1896, but retained the Winchester and Strasburg Railroad.
The Southern Railway gained control over track south of Strasburg. The Southern Railway preferred to direct traffic from the Shenandoah Valley east at Strasburg via its tracks to Alexandria, what had once been the Manassas Gap Railroad. The alternative was ship to northern customers via the B&O's Winchester and Strasburg Railroad and Winchester and Potomac Railroad, but Southern Railway revenues were increased by using Southern Railway track to Alexandria.1
Fairfax Harrison, A History of the Legal Development of the Railroad System of Southern Railway Company , Washington DC, 1901, p.472, https://www.google.com/books/edition/_/0IkjAQAAMAAJ (last checked April 14, 2020)
The Winchester and Strasburg Railroad continued in operation after the Baltimore and Ohio Railroad's 1896 bankruptcy. It remained part of the B&O system, which continued to invest in the Winchester-Strasburg route. It had built an engine house for locomotive maintenance at Strasburg Junction in 1887. In 1915, it converted the Strasburg Steam Pottery building into a new station combined with an office in 1915.
Passenger trains stopped traveling from Harpers Ferry to Strasburg in 1949, but freight traffic continues today.
The old Winchester and Strasburg Railroad became part of the CSX in 1987. The corporate existence of the Baltimore and Ohio Railroad was extinguished, and it became another "fallen flag" railroad.1
"Baltimore and Ohio Railroad Timeline," The Baltimore and Ohio Railroad Network, https://www.borail.net/Timeline.html (last checked April 14, 2020)
no railroad was built before the Civil War to connect the Winchester and Potomac Railroad (blue) with the Manassas Gap Railroad (red)
Source: Wikipedia, Map of the Manassas Gap Railroad and its extensions
the CSX still serves Strasburg, using the route of the original Winchester and Potomac Railroad and the Winchester and Strasburg Railroad
Source: CSX, CSX System Map