Operations began in 1980 over a section of ex-Pennsylvania Railroad's Frederick Secondary line from Taneytown to Walkersville, Maryland. Starting in 1983 the ex-Western Maryland Railway line from Emory Grove to Highfield was purchased from CSXT in sections. In late 1993, the company proposed a plan to rejuvenate the section of the Frederick Secondary from Taneytown to York, Pennsylvania that had been abandoned for the past ten years. The plan would have enabled to the company to expand its markets to Pennsylvania and would have provided a connection to Conrail's rail network. The plan proved to be too costly when landowners along the proposed route of rail reconstruction demanded excessive prices and construction never began. The railroad's business grew from trains pulling 200 freight cars per year in the 1980s to 18,000 freight cars in 2006. By 2006, it owned a fleet of ten locomotives; three GP9 low hoods, and seven GP38-3, all of EMD build. Its rolling stock also included 410 freight cars owned and/or leased. In 2008, the railroad was purchased by Genesee & Wyoming, a US-based corporation that owns multiple railroad shortlines in the United States and Australia.
Passenger excursion line
Gus Novotny Associates, Inc. began a passenger excursion services, known as the EnterTRAINment Line, on the Maryland Midland Railway system in 1989. The EnterTRAINMENT Line, was not part of the Maryland Midland Railway. It paid a "haulage fee" to the railway each time the EL operated a train. On board staff, such as kitchen crew, servers, bartenders, train manager, and faux conductor were EL employees. The Maryland Midland Railway provided engines and train crew for the EL excursions. The four owners of the EnterTRAINment line, Kirk Lorenz, Steve Hamilton, Don Golec, and Jerry Pilcher, purchased the EL from Gus Novotny & Associates in about 1992. Prior to the purchase, the EnterTRAINment Line ran a schedule of all-you-can-eat dinner trains, diner trains with murder-mystery themes, and carnival trains for children. The new owners added specialty theme trains, such as Civil War trains, political whistle stop trains, Santa Claus tree cutting trains, wedding trains, and NYE trains. The capacity of the EnterTRAINment Line also increased with new owners, as did the frequency and dates of departures. Group tour business was solicited, and marketing efforts expanded to include AAA, tour operators, and other nationally known travel partners. Dinner and Murder Mystery trains were operated between Westminster, MD and Union Bridge, MD, and between Union Bridge, MD and Thurmont, MD. Specialty trains operated between Union Bridge, MD, and the road's interchange with CSX at Blue Ridge Summit, in Pennsylvania. A dinner train or Murder Mystery train were typically made up of:
Power car to provide electricity to the train, and storage space
Dining cars, which consisted of old coach cars, with the coach seats removed and tables installed
Dance car, with oversized windows that opened all the way to the roof, and a live DJ
Dome car, a traditional center-dome car, formerly Union Pacific dome-diner 8008, later Auto Train 807
"Kitchen Car", two different types were operated, at first only a former "Lunch Counter Car" with a minute kitchen was used. It was later supplemented with a full dining car, complete with full kitchen.
Private Car. A couple of private cars were available for a premium price. Guests were offered private dining, and had the exclusive use of the car, it's bedrooms, and open platform, as well as the rest of the EnterTRAINment Line train.
"Hooper Car". The Edward G.Hooper, leased from a passenger car preservation group, was a former Baltimore & Ohio parlor car, and had the distinction of being named for a former president of the National Railway Historical Society. It also had its own bar, and bathroom facilities.
In less than two years, business on the EnterTRAINment Line quadrupled,. However, a dark cloud surfaced in the form of alleged back taxes due the State of Maryland. Because the EL was offering Murder Mystery trains, the State claimed that the EL must collect and remit to the State, the 10% Admissions and Amusement tax. The former owners had never collected this tax, and had indicated to the new owners that the "tax manner" was behind them. It wasn't. The EnterTRAINment Line's argument was that the entity was indeed a passenger railroad operating concern, and therefore not subject to local or state taxes, not under the enforcement or jurisdiction of the state, instead, under the jurisdiction of the Interstate Commerce Commission. The EnterTRAINment Line published a timetable with fares, one way, or round trip tickets were available to the general public on any train operated by the EL, and it ran over a line that was part of the ICC-defined, "national system". The new owners didn't do due diligence, and the State came after them for back A&A taxes of approximately $300,000. Mr. Pilcher left the company in about 1994, shocked that his partners had chosen to fight the State's allegations, without advice of counsel. The case was eventually decided in favor of the State, and the EnterTRAINment line soon stopped running. Much of the equipment was leased, and returned to its lessors. Other equipment was sold to other tourist railroads, and for a short while, some remnants of a dinner train operated out of the York, PA area. This service was discontinued when EnterTRAINment went out of business in May 1995. More recently, Maryland Midland has been a freight-only line, except for occasional trips by stockholders and the Western Maryland Railway Historical Society Museum, located in an adjoining building in Union Bridge.
Interchanges
Maryland Midland Railway connects with CSX Transportation at two points:
