Historians may dispute whether Stonewall Jackson’s Great Train Raid of 1861 ever really happened, but there’s no denying that, true or not, it makes a good tale.
The story goes that in April 1861, Jackson and his Virginia State Militia troops occupied Harpers Ferry. The trains in the area were part of the Baltimore and Ohio Railroad and were being used to transport coal to Northern naval bases. Jackson decided that this had to stop and so formulated a plan to capture the trains.
First, he complained to the B&O Railroad that the trains running at night were intruding on the soldiers’ sleep and asked that the trains only be run during the day. The Railroad complied, perhaps as a goodwill gesture to keep Jackson from destroying any of their track or cars. Then, a short while later, Jackson complained that the trains running during the day interfered with the training of his troops, and he requested that the Railroad only run their trains (both eastbound and westbound) during the hours of 11 a.m. and 1 p.m. So now, all the trains were running in the same area at the same time.
On 23 May, Jackson carried out his plan. The night before he had sent two teams of men to different points along the railroad (one to Point of Rocks, Maryland, and one to Martinsburg, Virginia). On the 23rd, they were to allow the trains to run as usual until noon. At that point, the troops in Point of Rocks were to stop all the eastbound trains while, at the same time, the soldiers in Martinsburg were to stop all westbound trains. This effectively trapped the trains on the tracks—a total of 56 locomotives and 300 rail cars, according to the story.
The account continues that then Jackson had the trains amassed at Martinsburg, where they stayed until late June, when Jackson’s men destroyed most of them as the troops withdrew. However, they kept 14 locomotives and transported those—by 40-horse teams—to Strasburg, almost 40 miles away.
The story is disputed by historians because it’s based entirely on one account—that of Captain John Imboden, who was known for not bothering to stick to the truth in his accounts of the war. That, combined with the fact that there are essentially no other primary records documenting the train raid, led to doubts about the story’s veracity. Historians do generally agree that Jackson did move trains by horse to Strasburg, but they believe he got the trains by taking over the train depot in Martinsburg—not by trapping them on the tracks.