Stonewall Jackson’s Great Train Raid – A Seminar & Tour

On October 5, 2018 - 18:00 - October 6, 2018 - 17:00
  • Activity Level: Easy

In the spring of 1861, shortly after the outbreak of the War, the Confederacy desperately needed to increase its l supply of railroad rolling stock. In response to this, Colonel Thomas J. Jackson contrived and executed a brilliant scheme to “appropriate” a large number of locomotives, railroad cars and other pieces of equipment from the Baltimore & Ohio Railroad, then under his control on the northern edge of Virginia. The result was an episode in the War Between the States, the logistics of which amazed officials on both sides of the Mason-Dixon Line.


However, some historians have disputed whether this amazing episode ever happened at all – but evidence continues to reveal that it did. We’ll do our best to shed light on this during our October trek.

Jackson’s plan was to amass and then trap rolling stock between Point of Rocks, Maryland and Martinsburg. To accomplish this, he informed B & O president John Garrett that the trains passing through Harpers Ferry at night were disturbing Jackson’s troops, and henceforth would only be allowed to move between 11:00 AM and 1:00 PM. The net effect of this curfew was to bottle up trains in yards on both sides of Harpers Ferry. Then Jackson sent troops to sever the rail lines at Point of Rocks and Martinsburg. On May 24, 1861, his men began to seize some 60 locomotives and nearly 400 railroad cars that had accumulated. They painstakingly dragged some of them to Winchester, and then to Strasburg. From there, some of the stock was moved by rail and some dragged by land, to Staunton, 125 miles from Martinsburg. At Staunton, the equipment was loaded onto the tracks of the Virginia Central Railroad and distributed throughout the South.

On our October seminar & tour, we will examine how the enterprise was executed, the personalities involved, and the obstacles that had to be overcome to implement the scheme. After dinner and talks on Friday night at our hotel in Winchester, our first stop on Saturday will be Point of Rocks, Maryland where the line was cut on the eastern end. Then, we’ll go down into the nearby old village of Harpers Ferry that figured so prominently in the raid and in other compelling chapters of the Civil War. Here, we’ll discuss the curious war-time relationship between Jackson and John Garrett and we will walk across the Potomac River Railroad Bridge to Sandy Hook, giving us the best possible view of the ruins of bridges across the Potomac including the piers from the Bollman Truss bridges that used to span the river.


After lunch in Charles Town, we will drive west to Martinsburg, where Jackson’s troops confiscated or destroyed many engines and cars and much railroad track. We will visit the Martinsburg B & O Roundhouse, and the oldest continuously operating railroad station in the U. S., dating from 1847. From there, we’ll drive south on the historic Valley Pike, past Bunker Hill and Stephenson Depot to Winchester, visit the old train station, and discuss how Jackson’s men, with the help of local wagoners, rigged special carriages and dollies to transport the purloined rail stock. In an incredible feat of engineering, they pulled Engine #199, weighing 85 tons, by 40-horse teams, rigged artillery style, through downtown Winchester all the way to the railhead in Staunton.

We’ll then bus south past Kernstown, Stephens City and Middletown to the Strasburg Museum, which became a depot for the Southern Railway in 1913. We’ll discuss how some of the captured equipment was placed on the rails of the Manassas Gap Railroad here and sent south to Staunton. Throughout, we will see Jackson at his finest, and will become familiar with the men who masterminded this daring exploit. In their wildest dreams, the James brothers couldn’t hold a candle to the eccentric former VMI professor when it came to “appropriations” of the iron horse.

We hope you’ll join us for this exciting autumn weekend program focusing on important but often overlooked Shenandoah Valley Civil War history. We have an attendance limit of 45 (one bus) so please enroll now.

Brandon H. Beck

Brandon H. Beck is retired Professor Emeritus of Shenandoah University & Director of its McCormick Civil War Institute. He is the author of 10 books on the Civil War including The Three Battles of Winchester: A History and Guided Tour; Third Alabama!: The Civil War Memoir of Brigadier General Cullen Andrews Battle, CSA; The Battle of Okolona: Defending the Mississippi Prairie; and Holly Springs, Van Dorn, the CSS Arkansas and the Raid That Saved Vicksburg

Stephen Lee Ritchie

Steve Ritchie is a veteran tour lead of Civil War tours in the Shenandoah Valley and is widely regarded as the leading authority on Turner Ashby. He is the co-director and co-founder of the Shenandoah Valley Civil War Institute of the CWEA, and the vice-president and co-founder of the Robert E Lee Fellowship.

Roy C. "Chip" Cather

Roy C. “Chip” Cather is a knowledgeable amateur railroad enthusiast who has studied the B &O Railroad for many years.

Registration Fee (Lodging Not Included) - $195

If You Must Cancel we will refund 100% of your fees paid or transfer them to another program, as you wish.

What is included in your registration:

·      The services of expert historians chosen for their knowledge and experience

·      Transportation to all sites as described

·      Friday Dinner & Saturday lunch

·      Refreshments and snacks during the tour

·      Map package and handouts




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We will be based at the Clarion Hotel (formerly Best Western Lee-Jackson Inn), 711 Millwood Avenue, Winchester, VA where we have reserved a block of rooms at the special nightly rate of $72.00 + tax, Single or Double. To reserve a room under our block, call 540-662-4154 prior to September 28, and identify yourself as a registrant for the CWEA tour.

WE'RE SWITCHING CREDIT CARD SOFTWARE so online registration is unavailable

FOR NOW, CALL 800-298-1861 to complete your credit card registration; or SEND CHECK to:


Box 78, Winchester, VA 22604

Friday, October 5

6:00 PM-6:30 PM         Cocktails - Cash Bar – Clarion Hotel (formerly Best Western Lee-Jackson hotel,)

                                                                       Winchester, Virginia

6:30 PM-7:30 PM         Dinner – Carved Steamship Round of Beef, Fried Chicken, tangy sides & salads, dessert display

7:30 PM-8:00 PM           "Ever-Bold: Jackson Decides to Solve a Railroad Problem" - Brandon H. Beck

8:00 PM-8:30 PM           "Riding the Rails: The Birth of a New State" - Stephen Lee Ritchie

Saturday, October 6

7:45 AM                         Bus Departs from Clarion Hotel in Winchester

12:00 N                         Lunch at Mountain Café in Charles Town, WV

5:30 PM                         Arrive Back at Clarion Hotel in Winchester

Great Train Raid 2018

We will be based at the Clarion Hotel (formerly Best Western Lee-Jackson Inn), 711 Millwood Avenue, Winchester, VA where we have reserved a block of rooms at the special nightly rate of $72.00 + tax, Single or Double. To reserve a room under our block, call 540-662-4154 prior to September 28, and identify yourself as a registrant for the CWEA tour.


Clarion Hotel
711 Millwood Avenue
Winchester, VA
United States