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7 Stunning Overnight Train Trips to Take With Your Kids

These overnight train rides — including New York to Chicago, and Los Angeles to Portland — are ideal experiences for family bonding.

A few summers ago, when my son Marcel was four, the two of us took an overnight train from Schenectady to Chicago and back over four days. It completely transformed our relationship. Before the trip, he wouldn’t let me put him to bed, cut up his food, or bring him to the bathroom. He’d say, “Can Mama do it?” creating all the problems you would expect. He did, however, want me to come along on the mythical “night train” trip that he had dreamed up; he’d been begging me for months. One night, in a moment of weakness, I answered, “Maybe this weekend” and set off a chemical reaction that was too much for his body to bear. His eyes lit up and he bounced around the room like a pinball. There was no backing out, so I bought a round trip ticket on the Lake Shore Limited, a name he’ll remember for the rest of his life.

My wife was stiff with worry. She vaguely predicted the deep-dish pizza eaten in Chicago too close to bedtime, the precarious neighborhood explorations, annoying theme songs, and rambunctious sleeper compartment behavior, but she never guessed that those few days of rattling along the rails would loosen the rigid parenting roles that were causing so much friction. To her, it felt reckless, but the theme songs had already begun. She allowed herself a smirk, arms still crossed, an implicit approval.

Three days later and a few hours into our ride, Marcelito and I were passing Rochester as fireworks from a minor league baseball game boomed over us in salute. I took a sip of my complimentary nip of Makers Mark; he took a pull from his tube of GoGurt and said “Dada, we’re best buddies, right?”

The views out the windows and inside the cars gave him even more reasons to ask “why?” He asked, “Why does the big lake look like an ocean?” “Why are they [Amish people] wearing those hats?” In Chicago, Marcel’s induction into a Low-Rider club in the Mexican neighborhood, Pilsen, and our dancing to house music at a street fair are shared memories in the bank. Headed home, another 20 hours with horrible Wi-Fi in a confined space led to dozens of games of war, the assembly of an intricate wooden grasshopper from a dollar store kit, and tantrums — like when he smashed the grasshopper — which forced my full patience and his full trust, the ingredients of a healthy attachment. It has been almost three years since that trip and his refrain ever since has been, “Can dada do it?”

I’ve now taken three such overnight train trips in the U.S. with my son, and, while I can’t guarantee they’ll have the same relationship-altering effect, I do highly recommend the experience to parents everywhere. While there are many excellent rides, the following routes, which include options from any region in the country are a great place to start. We picked start- and end-points we think are ideal. But play around with the Amtrak schedules to plan a trip that will include the specific sites you want to see and the length of time you think your family will enjoy onboard.

A Few Tips to Remember

1. Start with a one-nighter

My son was train obsessed — train shoes, train wallpaper, wanted to be a conductor — and even he struggled to maintain composure for the last couple of hours of the trip. You should test your child’s temperament with a relatively short trip first.

2. Book an actual room

Coach is much cheaper, but the roometes have an ingenious design: bathroom facilites, bunk beds, and a small table all fold away when not in use. Plus, it’s great laying in bed watching the sunrise. The rooms also include meal service, which has improved across Amtrak routes in the past year, especially on the western lines.

3. Hang out in the lounge and dining cars

Talk to strangers. They are the best part of train travel.

1. Lake Shore Limited

Route: New York to Chicago

Trip Time: 20 hours

You’ll cruise along the Hudson River going north and then west along the Erie Canal and the shores of Lake Michigan. Traveling between New York and Chicago by train you feel like you’re out on some depression-era gangster mission, playing cards and gnawing on pretzel sticks along the way–well, we did. Chicago is full of great family activities, and its most iconic food is kid-friendly. You could visit a bunch of famous Chicago hot dog spots (we loved Jim’s) deep-dish pizza spots (try Pequod’s) or taco places (start with Carnitas Uruapan).

2. California Zephyr

Route: Denver to Emeryville (near San Francisco)

Trip Time: 33 hours

Several porters we spoke to consider this route to be the most scenic. Leave from Denver, the best scenery is east of there anyway. You’ll pass through the great plains, witness stunning desert sunsets, and see stretches of the Rockies and Sierra Nevadas that are unreachable by other means. You’ll leave around 8 in the morning and arrive around four the next day so plan a lot of onboard activities. You could search for wildlife out the windows with binoculars or keep a checklist of natural landmarks. When you arrive in Emeryville, power up your dead legs with a hike around San Francisco’s hills or along the Emeryville Peninsula where you'll find great views of the bay not far from the station.

3. The City of New Orleans

Route: Chicago to New Orleans

Tip Time: 19 hours

This trip is ideal for beginners because it starts just before bedtime and finishes the next day around 4. Organize a playlist so that you can listen to electric blues on the way out of Chicago, delta folk blues through Mississippi and brass band music as you enter New Orleans. The richest city for culture in our country is vibrant all year long, but if you go during Mardi Gras season, you’ll give your kids lifelong memories of the parades. They aren’t all geared toward hard drinking, bead tossing college kids; several are appropriate for the little ones, and the costumes, music and floats are just as spectacular.

4. Silver Star

Route: Washington DC to Miami

Trip Time: 27 hours

Start the trip in the capitol, touring our national monuments and the brilliant Smithsonian Museums—the National Museum of African American History and Culture is an absolute must. The subsequent ride through the American south and the civil war battlegrounds will provide plenty of time for follow up discussions with the family. The ride curves over to Tampa and then back east to Miami where the vegetation becomes lush. Some recommended activities around Miami (Marcel and I did this trip last year): an airboat tour of the everglades; bike rides along South Beach; and Cuban and Haitian food in Little Havana and Little Haiti, respectively.

5. Coast Starlight

Route: Los Angeles, CA to Portland, OR

Duration: 35 Hours

The train departs from the big and beautiful Art Deco/Mission Revival Union Station in Los Angeles. It’s right near the historic Olvera Street, where you must load up on taquitos at Cielito Lindo—they have been luring crowds since 1934.

The Coast Starlight is the Zephyr’s biggest competition in the running for the most scenic route. For 350 miles it hugs the coast of the pacific, then cruises through California wine country and north past snow-capped mountains and lush pine forests of Oregon. Upon arrival in Portland visit Washington Park for trails, a Children’s Museum, and the World Forestry Center, then wind down at Old Town Pizza & Brewing.

6. Southwest Chief

Route: Los Angeles to Albuquerque

Duration: 17 hours

This is the shortest of our recommended trips. You leave around five in the evening and arrive before lunch the next day. On the ride, you’ll curve through narrow canyon passages, deserts, missions, and pueblos. If everyone is still feeling adventurous upon arrival in Albuquerque, you could take a hot air balloon ride, or go to a rattlesnake museum. The Indian Pueblo Cultural Center is a good place to start if you are interested in visiting a pueblo community. On the return trip, get off in Flagstaff for a couple of days and take a shuttle or classic train to the Grand Canyon.

7. Expedition Churchill

Route: Winnipeg, Manitoba, to Churchill, Manitoba

Trip Time: 1 day 21 hours

If you are looking for a polar express, this is about as close as you’ll get. Canada’s Via Rail, in partnership with the University of Manitoba, has created Expedition Churchill. The train travels through Canada’s arctic northern tundra to Churchill, known as “the Polar Bear Capital of the World” which sits on the Hudson Bay, the world’s largest inland sea. It’s an important site for climate research; frontline climate scientists will teach you about their latest research as part of the package. Go between February and March to see the Aurora Borealis and emerald-green skies at night; in May or June to see hundreds of bird species; kayak with the belugas in July or August, and for the most polar bear sightings, visit from July through November.