I grew up in New York, and I try to get back there at least once a year to see family and friends. In fact, a trip I took last week was the second in three months. In May, I stayed on Long Island with my high school friend Neil. We did fun, touristy things: a guided bike tour of Central Park, a bus tour of lower Manhattan and a boat ride into New York Harbor that included stops at Liberty and Ellis Islands.

Ellis was particularly memorable. The main building has been restored to something like its original splendor, and the educational displays are amazing. A century ago my mother, her parents, her two sisters, brother and grandfather all came through the island en route to their new American home on the south side of Chicago. My mother was born in Johannesburg, part of a cohort of Russian Jews who fled the Old Country in favor of the New. They stayed several years in South Africa, where work was plentiful and anti-Semitism rare.

“If they were doing so well in Johannesburg,” I recently asked my older cousin, “why did they come to America?”

“Better marriage prospects,” she said.

Last week’s trip, with Alan and Jim, two other high school friends, included watching a players’ practice round for the U.S. Open at the National Tennis Center in Queens, biking the magnificent 500-acre Storm King sculpture park nestled in the Hudson Highlands and visiting the New York Botanical Garden in the Bronx.

In both cases I flew into LaGuardia and came home on an Amtrak train, the storied Lakeshore Limited.

What is it about trains? I always struggle to explain their mystique, their hold on me ­– and can never do it justice. Part of it is the magic of youth. As a kid growing up in a New York suburb much like Evanston (only with hills), I frequently rode the New Haven commuter train to Grand Central Station with my dad, who was an executive for a dress manufacturing firm headquartered in Manhattan’s Garment District. While he made Saturday morning long-distance calls to his salesmen, I traipsed around midtown Manhattan, goggle-eyed at the seedy lure of 1950s Times Square.

Best of all, and what really sparked my train mania, were the overnight train rides from Grand Central to Portland, Maine, where I attended a nearby boys camp for three summers. Gazing out at the passing parade of upstate New York and New England – the small towns, the village squares, the homes and backyards, the stores and factories – one witnessed a rarely seen panorama of America’s soul.

During a college year abroad in 1967 and ’68 (in which I mostly traveled), I joined three dozen students from around the world for a late December trip from London to Russia. Our two-night train ride to Moscow took us through East and West Germany. The border between them was a miles-long hellscape of nothingness lit by giant klieg lights from massive guard towers. The next morning we rode into the two Berlins. The train was sealed, meaning no one could enter or exit. In East Berlin I decided to test the limits: I walked onto the rear car’s outside platform as if I had every right to be there. A soldier with a submachine gun motioned me back inside. He had the stronger right.

We were met at the Soviet border by a luxury Russian train, complete with samovars at each end of the car.

Our group spent five days in Moscow, four in Leningrad (today’s St. Petersburg) and four in Warsaw. We saw David Oistrakh and the Bolshoi Ballet in concert. I swam in Gorky Park, snow falling gently on our heated pool. Altogether 17 days, $170. The Kremlin, Red Square, the Hermitage, the old city of Warsaw, plus­ the train rides across western Europe were all part of a uniquely memorable experience.

Here in America I’ve ridden overnight trains from Chicago to New York, Austin and San Francisco. My wife and I took the old Coast Starlight train from Seattle to San Francisco, which, true to its name, provided unforgettable nighttime vistas of mountain lakes bathed in starlight.

Which was a highlight of this last train ride. At some point after darkness had descended, hours after we had left Penn Station, we passed over a midsize river. Moonlight twinkled merrily on the surface. I grabbed my phone and checked the GPS. It was the Buffalo River. The Buffalo touches Chicago: it drains into Lake Erie, separated from the Evanston shore by Lake Huron. All things connect, like trains criss-crossing the continents.

Les Jacobson

Les is a longtime Evanstonian and RoundTable writer and editor. He won a Chicago Newspaper Guild best feature story award in 1975 for a story on elderly suicide and most recently three consecutive Northern...

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