One of the early goals of the Western Maryland Railroad was to reach Hagerstown and Williamsport in Washington County, Maryland. Williamsport, in particular, would have been an attractive destination. At that point, coal from the Chesapeake & Ohio Canal boats could have been offloaded onto rail cars to go to Baltimore. This would have allowed the railroad to compete for coal against the Baltimore & Ohio Railroad, which reached Cumberland in 1842 and had continued westward.

In 1864, Joseph S. Gitt conducted three studies on behalf of the railroad to evaluate routes from Union Bridge, Md., to Hagerstown. These were called the Mechanicstown route, the Emmitsburg route, and the “Middle” routes. For two years, railroad officials debated the best way to traverse Catoctin Mountain and South Mountain to reach Hagerstown.

“In this confused period, proposed routes were changed almost daily,” Harold A. Williams wrote in The Western Maryland Railway Story.

As the railroad company prepared to ask for construction bids, John Lee Chapman, the mayor of Baltimore, got an injunction against the Western Maryland Railroad to “restrain the company from giving out, or consummating the contract.” The City of Baltimore was a large stockholder in the railroad, and as such, could approve or veto, and proposed route. Chapman favored the middle route, but when opinion moved away from it, he got the injunction to stall the process.

The Mechanicstown Route was selected and the railroad reached the town in 1871. Now, the railroad faced the tougher problem of crossing Catoctin and South mountains. The best option was for the railroad to pass into Pennsylvania near Emmitsburg, Md., for a short distance. In essence, this route would allow the railroad to go around the steepest parts of the mountain.

This solution had its own problem, though. The Pennsylvania legislature had adopted a law that in order to get a charter in the state, the Western Maryland Railroad would need to pass the Waynesboro Turnpike at Liberty Mills, which was about 1.5 miles north of Emmitsburg, and the Gettysburg Railroad (the Gettysburg would not come under the control of the Western Maryland Railroad until 1909) would be allowed to connect to the Western Maryland Railroad at a point in Pennsylvania.

Chapman, who had become president of the railroad in 1866 while he was still mayor of Baltimore wrote, “This action would have compelled us, by going into Pennsylvania, to lengthen our Road some six or seven miles over our present route, to avoid the State of Pennsylvania entirely.”

The Western Maryland Railroad directors wanted to stay in Maryland to avoid the complications that being in Pennsylvania would create. Variations on the proposed routes were considered.

Chapman described the final route, writing, … it will pass through Middleburg and within five miles of Taneytown, Johnsville and Woodsborough, within six miles of Emmittsburg, and within two miles of Creagerstown, through Graceham and Mechanicstown, and within three miles of Catoctin Furnace, and then passing up Owings’ Creek Valley, where Iron Ore abounds in the line of the Road, passing through Harbaugh Valley it reaches the summit of the Blue Ridge, which crosses within one mile of Monterey Springs, and within six miles of Waynesboro. It then passes down Germantown Valley, taking the west side of Mount Misery, through Smithsburg and Cavetown to Hagerstown.”

While theoretically feasible, financially, it would stretch the railroad’s resources, but for the railroad to survive, it needed to push further west. However, this created some short-term issues between the railroad and the contractors over costs. Also, the city of Baltimore got another injunction to stop the extension from Hagerstown to Williamsport because of the cost to the city as a shareholder. Besides, the city already had coal coming into the city along the B&O, so having the Western Maryland Railroad bring it in from Williamsport represented no gain for the city.

These issues were eventually worked out, construction continued and reached Sabillasville, Md., on Catoctin Mountain on August 28, 1871.

The railroad’s annual report for 1871 noted that the railroad had run into additional construction problems beyond scaling a mountain. “Almost insurmountable difficulties have been overcome in the removal of the hard copper rock by the contractor in his progress through the rockcuts approaching Blue Ridge or Monterey Summit.”

Since this was before dynamite was used for blasting, the copper rock formations did present an insurmountable problem. Removing them with black powder would have been dangerous and perhaps created other problems with the topography.

The engineers returned to their maps to try and figure out an affordable way around the problem, and once again, they looked to the north and Pennsylvania.

With this seeming to be the only feasible solution, they had to study a way to make the restrictions created by the Pennsylvania legislature feasible.

The solution found a loophole in Pennsylvania law and got the railroad around the copper formations. It was determined that the railroad only needed to go into Pennsylvania for a few hundred years. The company purchased farmland along the border and then ran their tracks across private property, which did not necessitate them needing a charter from Pennsylvania.

It was a cheaper solution that got the railroad around the worst part of the mountain and back on track to Hagerstown.

With some creative thinking, the railroad continued west and reached Hagerstown in 1872.