I’ve always been fascinated by the influence of topography on where humans have decided to set up camp over the millennia.

Here in the Chesapeake Bay region, as recently as a few centuries ago, settlements in coastal areas were all about water: The best place to live was along a navigable river or creek, so that canoes and rafts and boats and ships could bring you stuff and people, or take away stuff and people.

Farther west in the Appalachian Mountains, though, waterborne transportation is less workable. The rocky rivers, creeks and streams that lead to the Bay have helped shape the land, but the placement of communities — and travel between them — has historically depended more on gaps and passes and hollows and valleys.Excursions on the Western Maryland Scenic Railroad are a popular way to enjoy fall colors along mountain towns and Potomac River headwaters. Be sure to reserve your seat in in advance. (Western MD Scenic Railroad)

Take, for example, the trip from Cumberland to Frostburg in Western Maryland. In fact, take a train from Cumberland to Frostburg — on the Western Maryland Scenic Railroad — and you’ll see exactly what I’m talking about. Sure, you can draw a straight east-west line on the map from one town to the other, but out here, where the hills and ridges lie on the landscape like wrinkled sheets, there are precious few straight lines available to the traveler. Unless you’re prepared to hike over half a dozen steep ridges, the only way to go is north and around or south and around.

The south-and-around route is via the modern highway — taking Interstate-68 (US 40) out of Cumberland, through the hollow below La Vale, across the valley that gives La Vale its name, then through the Braddock Run gap between the steep ridges west of Frostburg.

The Western Maryland Scenic Railroad, in contrast, goes north and around, chugging out of Cumberland along Wills Creek, a tributary of the North Branch of the Potomac River that carves a dramatic gap through the ridge just west of town. This is called the Narrows — or, if you’re inclined to match nature’s drama, the Gateway to the West. A mile or so north of the Narrows, near Corriganville, the track hairpins twice before settling into a more or less westerly-then-southerly route, roughly parallel to Maryland Route 36 and Jennings Run the rest of the way to Frostburg.

I boarded the Frostburg Flyer with about 50 other passengers on a fall morning at the Cumberland station. Ranging in frequency from two to six days a week, depending on the season, the Flyer departs at 11:30 a.m. for the roughly hourlong trip to Frostburg.

Our tour guide, speaking to us over the train’s PA system, was an entertainingly chatty gentleman named Bruce Pfeifer — authentically clad in a shirt and tie, denim overalls and a pinstriped railroad cap.

As we approached the first hairpin turn, Pfeifer told us to be on the lookout for the so-called Bone Cave. A minute later it appeared — about 20 feet from the tracks at the foot of a rock wall, a craggy human-sized hole desultorily closed off by a rusty chain-link gate. Railroad workers discovered the cave a century ago, Pfeifer said, and it turned out to contain some truly remarkable Pleistocene-era fossils, including that of the long-extinct saber-toothed cat. Reconstructed skeletons from the cave have been on exhibit at the Smithsonian Institution since 1974, he said, as part the National Museum of Natural History’s exhibit of ice age mammals.

A train on the Western Maryland Scenic Railroad travels through the snow-covered landscape of Allegany County. (Western MD Scenic Railroad)

Shortly after the second horseshoe bend, called Helmstetter’s Curve, a little boy about 5 years old, with exquisitely shiny black hair, popped up over the seatback in front of me, looked at me for few seconds, then looked out the window and asked, “Why do we keep turning? Are we going back?”

I wasn’t sure if he was asking me or his father, who was in the window seat next to him. When the father said nothing — or nothing I could hear — I said, “You mean the train? Why does the train keep turning?” He nodded. I said, “Um, well…” Then the father said, “No, buddy, we’re not going back yet. We just have to go around a lot of mountains.”

That was a good answer. Mine was going to be, “Because it has to follow the tracks, and the tracks turn a lot.” But dad’s reply was way better; it spoke to the landscape. And it seemed to satisfy the boy, whose name was Taylor, I learned in a later conversation about bears. (They’re out there, he told me, but, according to his dad, “They’re way back in the woods and won’t bother anyone.”)

After Helmstetter’s Curve, where farm fields sprawl on both sides of the track, we dove back into the woods for about 2.5 miles — passing through a nearly 1,000-foot tunnel along the way. When we emerged from the woods near the town of Barrelville, roughly the halfway mark to Frostburg, Pfeifer pointed out a long procession of wind turbines on a mountain ridge off to the northwest. They seemed enormous, even though they were actually 3.5 miles away, across the state line in Somerset County, PA.

After another dip and hairpin curve through Woodcock Hollow, we came within 1,000 feet of the town of Mount Savage, though the thick woods obscured any view of the town itself. There’s a certain irony to that, because Mount Savage is why the railroad is here in the first place. By the 1840s the town had become a little industrial beehive, with coal mining, clay mining, three iron furnaces, a thriving brick works (which operates to this day) and a locomotive manufacturer.

Hence the need for what was called the Mount Savage Railway when it opened 1845 — built for the primary purpose of carrying the town’s products and raw materials to Cumberland. From there, they could go anywhere, by rail, C&O Canal or National Pike.

Several decades later the line became part of the Western Maryland Railway, which at its peak ran clear across the state and into West Virginia and Pennsylvania. That company lasted into the 1970s, by which time it had all but vanished in a series of rail line mergers — Chessie, C&O, B&O and finally CSX. Then, in 1988, came the Western Maryland Scenic Railroad, which has operated the Cumberland-to-Frostburg excursion ever since.A conductor chats with guests on a holiday ride on the Western Maryland Scenic Railroad. A variety of dining options and different themed tours are available throughout most of the year. (Western MD Scenic Railroad)

This stretch of right-of-way also accommodates more than trains. Just as I had begun to wonder why we were seeing so many hikers and bicyclists along the tracks, Pfeifer answered the question. For most of its 16 miles, the railbed doubles as the Great Allegheny Passage — the 150-mile trail that, combined with the 185-mile C&O Canal trail, makes it possible to walk or pedal from Washington, DC, to Pittsburgh.

A couple of miles past Mount Savage, we came at last to the tidy Frostburg Depot. With a one-hour layover there, we had some options. After watching the train’s lumbering black engine spin around on a huge turntable just beyond the depot (That was a must-see, Pfeifer said, and he was right.), we could stay there and visit the Thrasher Carriage Museum, just behind the depot —which should have been open, according to its sign, but wasn’t — or grab a bite and a beer at the Trail Inn Café, right next to the turntable. Or we could explore Frostburg’s Main Street, part of the historic National Pike, which is just up the hill about two city blocks away. Those would be two very vertical city blocks, mind you, by way of a giant multi-tiered wooden staircase and an uphill path along Depot Terrace. I chose the latter option, exploring a quarter mile or so of Main Street before heading back to the depot for the return trip.

For the time being, the railroad’s mixed-vintage passenger cars are hauled by a 1960s diesel engine — assisted, when the number of cars and passengers calls for it, by a recently acquired second diesel. But for most of the Western Maryland Scenic Railroad’s 30 years, the star of the show had been its century-old steam locomotive, No. 734, nicknamed Mountain Thunder. Built in 1916 for a Michigan railroad, Mountain Thunder was acquired in 1991, when the excursion tours were brand new, and served the line for nearly 25 years. In April 2016, the engine had to be pulled out of service for a federally required rebuild and inspection — a process that can take years.

Another vintage steam engine has been in the wings since 2014, and it’s a doozy — C&O Railroad locomotive No. 1309, called Maryland Thunder. This huge two-engine behemoth, built in 1949, was the last commercial steam locomotive made for  a U.S. railroad. The Western Maryland Scenic Railroad purchased it in 2014 from Baltimore’s B&O Railroad Museum, where it had been on display since the early 1970s.

The plan was to have Maryland Thunder up and running by early 2017, but it needed a lot more work (meaning a lot more time and a lot more money) than first estimated. The latest cost projection puts the total rehab at $1.8 million, and the expected completion date is “some time in 2019.”

So, for now, the two not-so-glamorous diesel engines will have to do the work — carrying around 30,000 passengers a year, weaving through hills and hollows and horseshoe bends from Cumberland to Frostburg and back again, demonstrating to all that out here, where the land was long ago shaped by winding, gravity-driven water, there are precious few straight lines.

The Western Maryland Scenic Railroad’s regular Cumberland-to-Frostburg excursions run from March through December. The schedule varies by season, from two to six trips per week. For children, the Winterland Express, featuring Santa and elves, runs four times every weekend between Thanksgiving and Christmas. For adults, generally two Saturday evenings per month in season, there’s an evening murder mystery excursion, including dinner. Ticket prices range from $30/child and $46/adult (standard coach, no meal) to $99 or more, depending on special themes, events and dinner options. Cyclists can take their bikes on the train for a small additional fee. For information, visit wmsr.com or call 800-TRAIN50 (800-872-4650).