A great American rail trip: Big Apple to the Windy City

From buzzy New York through sleepy, small-town USA, a 950-mile ride to Chicago makes for some classic American train travel.

Platform 7 of Pennsylvania station feels like a dungeon. Dim lights flicker in a gloomy enclosure where our sleek Lake Shore Limited service awaits, its engine rumbling quietly in the dark. Down a narrow platform crammed with passengers, I reach carriage 12, where I find my sleeper cabin. It’s about the size of a camp bed and has a tiny loo and a metal sink.

We pull away. A horn echoes and, beyond a long tunnel, we rise slowly into the afternoon sunlight. Glimpses of the muddy-brown Hudson river flit between tower blocks. Razor wire runs along a wall by a factory; “BEAST,” says graffiti by a fence. Then the riverscape opens up. Thick forest covers the far bank.

It’s startling how quickly the Big Smoke disappears when you leave New York City by train. Not so long ago I was in a traffic jam in a yellow cab, about to enter the hectic concourse at Penn station. Now I’m in Huckleberry Finn land, with little uninhabited islands and shafts of soft sunlight playing on russet and lime-green trees. Metal-framed bridges soar high. The river winds onwards beyond a marsh of lilac-tipped reeds.

New York City to Chicago on this Amtrak service provides a great first taste of American train travel, transporting you in a few minutes from Manhattan’s skyscrapers to sleepy small-town USA. I’m on a journey that takes 19 hours, covering 959 miles, about a hundred miles farther than the drive from Land’s End to John o’Groats. And I’m about to see a whole lot of places that I might never have laid eyes on if I hadn’t taken to the tracks.

Round a bend of the Hudson — which the tracks follow — we’re soon passing the picket fences and colourful houses of Irvington (former home of the Rip Van Winkle author, Washington Irving), Croton- Harmon, Peekskill and Garrison (the station for West Point military academy).

We draw to a halt at the town of Poughkeepsie, near an Irish pub and a fishing jetty. This is where the Vanderbilts and Astors had their weekend retreats, and is where Samuel Morse, the inventor of the telegraph and Morse code, lived — so says my copy of Lake Shore Limited Route Guide, provided free in the sleeper cabins.

“Albany’s comin’ up. Albany’s comin’ up,” the attendant says over a speaker. And so it does. Passengers leap out at the station for the capital of New York state, going for a quick platform smoke close to a sign warning: “IMPAIRED DRIVERS TAKE LIVES”. Perhaps this message is necessary because the city’s bars have a “last call for alcohol” at 4am, later than elsewhere in America.

In the dining carriage (all meals are included) I sit at a blue-leather booth, where I’m joined by Stan, a plumber, and Bette, who works in computing. They’re from Oxford and are on a fortnight train trip from New York to Chicago and Washington because they like the adventure of trains.

The Lake Shore Limited train takes little time to leave New York City behind for Huckleberry Finn land

We eat our Amtrak Signature Steaks, served with a peppercorn sauce and a baked potato with sour cream and vegetables. Seven out of ten is Stan and Bette’s verdict, although I think they’re being pretty generous; the steak is as tough as an old shoe. Then we discuss the little cabin loos. “There should at least be a dividing curtain,” says Bette. The toilets are, we agree, ridiculously prominent in the cabins.

They disappear to their cabin and the offending toilet, while I head to the bar for a Sierra Nevada Regional Craft Ale ($7, or about £5.50). The woman attending the bar fetches a bottle and levers off the cap using a crack in the ceiling above the booth. She catches the cap as it falls, almost without looking.

It’s dark now; shadowy outlines of buildings and trees slide by. Beer in hand, I sit in the dining carriage. After my drink I stroll along a couple of darkened carriages to see how those who don’t have sleeper carriages are faring. People are sprawled with legs in aisles. Films flicker on iPads. A man wrapped in a blanket holds a little dog. I hadn’t expected pets on board. The restroom is a disaster zone (I shall say no more). Of the 263 passengers on board, two thirds don’t have sleepers — and it looks quite rough round the edges.

I retire, gratefully, to my cabin, where, when a freight train passes, it feels as though the air is being sucked away. I sleep well enough, though, lying on one side (there’s little room to move).

By morning, the scene outside the windows is of fields of golden crops: the American countryside in all its glory. I take a shower at the end of the carriage — although the water runs out when I’m still covered in soap, I manage to splash on enough to remove the suds.

We move on into Ohio, heading for Sandusky, part of the “Underground Railroad that helped slaves escape to freedom before the Civil War”, says the Lake Shore Limited Route Guide.

Trains have been rolling along this route since the mid-19th century, when railroad frenzy was at its height, resulting in a vast spider’s web of lines across a nation that was growing rapidly on the back of the network.

The route here was formerly part of the New York Central Railroad, once controlled by the great railway magnate Cornelius Vanderbilt, who rose from a humble background to become one of the most powerful businessmen in the US. It was a key link between America’s two most important cities in the 1850s, with tracks from sea to sea finally completed on May 10, 1869, when they were joined at Promontory Point in Utah — a hugely symbolic moment in American history.

At breakfast I meet Larry, from Michigan, who introduces himself as he sits down opposite me at one of the booths.

We order Railroad French Toast and Larry hands me his card: “H Lawrence Swartz, PhD, Chairman & CEO, America by Rail . . . the best way to see America!” I am, by chance, eating breakfast with the founder of the “number-one group travel company with Amtrak”. Larry founded his company in 1983. It’s now run by his son, taking 3,000 holidaymakers on tours each year. “ I just love trains,” says Larry. “Trains are wonderful. On a train, people can talk; they’re going somewhere, but they’re not going anywhere. They have the time.”

Toledo comes and water supplies are replenished as passengers come and go. We roll west across bridges, passing container carriages, picket fences, Stars and Stripes, the small town of Bryan, the even smaller town of Waterloo. On we go, and on, until finally we see Chicago.

The horn blows. We draw to a halt. We’ve arrived at Union station — from one set of skyscrapers to another, with a whole lot of America in between. From here the country opens up: Texas, California and Washington await, informs the flickering departure board. I get ready to move on to Minnesota, and to Seattle after that; the New York to Chicago line is the start of many an adventure.
Tom Chesshyre is author of Ticket to Ride: Around the World on 49 Unusual Train Journeys (Summersdale, £9.99)

Need to know
Tom Chesshyre was a guest of Brand USA (visittheusa.co.uk). Amtrak (amtrak.com) has New York to Chicago “saver” seats on its Lake Shore Limited service from about £53; a “viewliner roomette” sleeper for two is from about £466, with meals included. Bon Voyage (0800 316 0194, bon-voyage.co.uk) has a seven-night break with three nights in New York at a four-star hotel, a New York-Chicago Lake Shore Limited overnight train with a sleeper cabin and meals, and three nights in Chicago at a four-star hotel from £1,439pp, flights included.

All aboard — classic US train rides

Coast to coast
Board a series of trains from New York to San Francisco, stopping in Washington, Chicago, Denver, Arizona (to see the Grand Canyon) and Los Angeles. New York to Washington is a day trip, followed by two nights in a hotel in the nation’s capital. The onward train to Chicago takes the historic B&O line (Baltimore and Ohio Railroad) via Pittsburgh and Cleveland to Chicago. Next is the California Zephyr service to Denver and a journey along the Denver and Rio Grande Western Railroad through the Rocky Mountains. Rides on the Grand Canyon Railway, Amtrak’s Southwest Chief overnight service to Los Angeles and Coast Starlight to San Francisco come next.
Details A 21-day USA Coast to Coast tour is from £3,995pp, including flights and hotels (01904 521936, greatrail.com)

Texas adventure
See the sights in the Lone Star State, starting in Dallas and travelling south by train to Austin, then to the charming city of San Antonio. This nine-day, self-guided rail holiday begins with the chance to visit Fort Worth Stockyards, and the John Fitzgerald Kennedy Memorial and museum commemorating JFK’s life in Dallas. After a couple of nights you catch Amtrak’s seven-hour Texas Eagle service to Austin, the state capital and home to some of the best steakhouses in America, as well as excellent art galleries. Two nights are spent in Austin. The train to San Antonio is three hours and you stay three nights in the city. Among the recommendations is a visit to the Alamo and a walk along the restaurant and bar-lined River Walk.
Details A nine-day trip is from £1,695pp, including flights and hotels (0800 316 3012, bon-voyage.co.uk)

Tour around Alaska
Explore America’s far north on a self-guided train trip, travelling from Anchorage to the city of Fairbanks. Before heading to Fairbanks, there is a four-hour train ride to the south of the state on the Alaska Railroad, to visit the port town of Seward and Kenai Fjords National Park. Then there’s the return four-hour journey, followed by a three-hour trip to Talkeetna, where a wildlife trip to spot beavers, moose and bald eagles is included. Later it’s on to Denali (three hours), staying overnight and enjoying another wildlife tour, and on to Fairbanks (four hours) to take in Athabascan Native American culture.
Details A nine-day trip is from £1,889pp, with hotels but excluding flights (01737 214 250, www.discover-the-world.co.uk; returns to Alaska via Reykjavik are from £750 (020 7874 1000, icelandair.co.uk)

Chicago to New Orleans music trail
Start in Chicago on a 12-day sightseeing and train trip that ends in New Orleans, taking in some of the best blues, jazz and rock venues in America. After two nights in Chicago, with its many jazz clubs, it’s on to Memphis from Union station on Amtrak’s overnight City of New Orleans sleeper service. In Memphis you can visit Sun Studio, where Elvis Presley and Johnny Cash recorded early tracks, and there’s a chance to enjoy live blues on Beale Street. Three nights are spent in Memphis. Afterwards, catch a train to New Orleans for jazz and blues on Bourbon Street, in the heart of the Big Easy.
Details A 12-day Railroads & Rhythms trip is from £2,595pp, with flights and hotel included (01904 521936, greatrail.com)