Before politicians, celebrities and business titans traveled the world by private jet, they traveled by private train. President Franklin Delano Roosevelt had a private car specially outfitted during World War II. The actor Cary Grant is said to have courted the Woolworth heir Barbara Hutton aboard a private car. The Catholic Church even had one for a U.S.-based cardinal.
But, as the 20th century advanced, passenger rail gave way to car and plane travel. Postwar America began to travel differently, and so too did the rich and famous, who eschewed train cars for private planes. Private rail travel disappeared.
Well, almost. Amtrak, the national railway company, and a dedicated but dwindling set of enthusiastic owners, have kept private train travel alive by way of something called the Privately-Owned Rail Car Program, which charges owners of private rail cars a fee per mile to hitch them to existing Amtrak trains.
Private rail cars traveled 429,000 miles on Amtrak in fiscal year 2025, according to the American Association of Private Rail Car Owners, accounting for $2.5 million of Amtrak’s $3.9 billion in revenue last year — hardly a significant line in the budget.
But owners see themselves as something more than the numbers convey: stewards of a forgotten history.
All Aboard
On an early May morning, I joined a line of passengers in Chicago’s Union Station waiting to board the Lincoln Service Missouri River Runner bound for St. Louis. But I was not getting on an Amtrak car. I was joining a private car owner named Patrick Henry on what’s called a “repositioning run” for three of his cars — he was moving them, without passengers, to Kansas City for their annual inspection. (I bought a standard Amtrak ticket for my portion of the trip for $41.)
Spotting me in line, Mr. Henry, 74, waved me under a barricade and then guided me through Union Station’s dark bowels to his crisply painted blue-and-white cars. U.S. and Texas flags hung on the rear car’s back platform. Amtrak had already hooked the cars onto the back of the train. As I climbed the stairs, Mr. Henry’s onboard manager, Olivia Estrada, greeted me and took my drink order.
Mr. Henry named his first two cars, purchased as a pair in 2004 for $900,000, after his parents: Warren R. and Evelyn Henry. He recently added a 1954 Pullman named Santa Fe — the railroad for which his father worked for 41 years. He declined to share what he paid, but a car immediately ready for Amtrak typically costs around $1 million. Maintenance costs Mr. Henry $60,000 annually on the domed Warren R. Henry car, and $40,000 for each of his two other cars, which are sleepers.
Mr. Henry showed me to the second floor of the Warren R. Henry, at the rear of the train. A dome car, its big windows offered a view of the passengers making their way toward Amtrak’s cars in front of us. I felt uneasy looking down on them. I also had no envy for the seat scramble they would soon face, as I chose between six creamsicle-colored swivel chairs. Some passengers stared or paused to take a photograph, possibly wondering what I was doing up there.
Mr. Henry, who runs a beverage marketing company, uses his cars for personal travel and charters them out at $16,000 per day for the dome car and one sleeper car — a rate that includes meals, drinks and Amtrak fees.
As we pulled out of the station, the Willis Tower and Chicago River came into sight. The elevated perch gave sweeping views of Illinois’s industrial towns and farmlands. Windows encased the side and back, with cushioned leather seating throughout.
Below the upstairs lounge was another lounge with a TV and a dining room with a long table and a stained glass panel on the ceiling. Mr. Henry has equipped the cars with Starlink satellite internet.
Though I wasn’t sleeping on the train, I had been given a bedroom on the Evelyn Henry with its own sink but a shared bathroom. The car’s primary suite has its own bathroom. All the Santa Fe’s bedrooms have their own bathroom and shower. The two sleeper cars house a combined 12 bedrooms.
‘The best-kept secret in transportation’
Leonard Cherry has chartered Mr. Henry’s trains three times and finds rail travel soothing. “It’s like being rocked to sleep at night,” he said.
Mr. Cherry, a 71-year-old Houstonian who sold his material supply and demolition company in 2020, said a weeklong trip typically costs $10,000 per person.
Mr. Cherry and his wife, Regina, got hooked on train travel after a 2009 Amtrak trip from Chicago to San Francisco. They loved the spectacular scenery but found the accommodations cramped. Mr. Cherry researched high-end train experiences and found Mr. Henry.
“It’s probably the best-kept secret in transportation,” he said.
Mr. Cherry compared the experience to yachting, where the journey can be more important than the destination.
“What we prefer is to sit in the dome car and play cards or games and have interesting conversation and dine well and listen to good music as we enjoy the scenery,” he said.
Guests can book trains directly through Mr. Henry or through a company called Halloway, which aims to be private rail travel’s Airbnb. Mike Avena launched the company in 2025, planning to start a North American night train service. Looking for cars to bring his vision to fruition, he connected with car owners and saw an opportunity to grow the industry.
Mr. Avena said the owners operate a “paper-based business” and have “struggled to connect with a newer generation of travelers.” Halloway now offers a handful of private railroad cars that can be chartered, and also operates the Napa Valley Wine Train and the Head of the Lakes train along Lake Superior.
Bill Gray, the president of the American Association of Private Rail Car Owners, owns a rail car called the Blue Ridge Club, which he charters through Halloway. Chartering the car without Amtrak fees, food or crew costs $2,750 per day. He said he spends $50,000 per year on maintenance, though he declined to say how much he paid for the car. It sleeps six people, fits 20 in its dining room, and eight in its lounge.
Terry Tomsick, an attorney and medical ethicist from Colorado, rode the Blue Ridge Club last October, on an eight-day fall foliage group trip through New York and Vermont for which she paid $5,500.
“You get to see a part of the world that is available only by rail,” she said. “You’re going through wonderful vistas, and you’re stopping in the little towns where you’re usually parked overnight, so you get to go into the little towns for the evening or afternoon.”
Trying to keep history alive
Amtrak’s focus on speed and on-time performance can put it at odds with private rail cars. The Blue Ridge Club, which Mr. Gray parks in New Jersey, can’t exceed 110 m.p.h., because, like most private cars, it does not have the dual-brake technology required for higher speed testing. Amtrak consistently goes faster than that in the Northeast.
Amtrak began raising its rates for private rail cars in 2019 following an Inspector General’s report that found the rail agency’s program had “insufficient controls for cost and revenue management.” As of Oct. 1, owners who attach certified cars to Amtrak trains will be charged $4.91 per mile, with each additional car costing $3.78 per mile, up from $2.90 per mile for the first car $2.22 additional cars in 2017. (The cost for a first car peaked in 2023 at $5.01 per mile.)
As Amtrak costs rise, the number of Amtrak-certified cars within the American Association of Private Rail Car Owners has dropped to about 38, from 125 a decade ago, according to Mr. Gray.
Borden McGahee and her husband, Nelson, of Columbus, Ga., purchased the Dearing private car for $140,000 in 2006. She said they stopped taking it cross-country in 2019 because of Amtrak logistics and costs. Their parking rate in Savannah reached $2,000 per month. The car is now on a tourist train in Georgia.
“I hate that we can’t do it anymore,” Ms. McGahee, who declined to give her age, said of traveling on Amtrak’s network. “We had this car to keep history alive.”
Marc Magliari, an Amtrak spokesman, said attaching the cars can take up to an hour and requires turning off the HVAC, toilets, regular lighting, food service and power outlets on the rest of the train for most of that time. On June 1, Amtrak cut six cities where private rail cars can hook on. It also added two new cities in California.
Farmland and tiramisù
Aboard the Warren R. Henry, we zipped through Illinois towns, approaching 110 m.p.h. Railfans gawked, snapping photos as we went by. Students congregated in the Joliet, Ill., baseball stadium near the Amtrak station. I thought they were there for us. It turned out they were just watching a baseball game. We passed through industrial towns with roadways and railways feeding into intermodals like spider webs, and vast green and yellow expanses of farmland.
As lunchtime approached, Ms. Estrada draped white tablecloths over the two booths in the dome car, set the table and placed menus: braised short ribs, Carrabbas whipped potatoes, grilled asparagus, and tiramisù, using recipes based on former railroad menus.
Ms. Estrada started working as a cleaner for Mr. Henry. When she took the job, the only other train she’d been on was New York’s subway. “I just got spoiled immediately,” she said.
As we snaked over the Mississippi River, St. Louis’s Gateway Arch came into view, signaling the end of my journey.
The cars could keep going without me. After their inspection in Kansas City, Mr. Henry had other plans for them.
At St. Louis’s Gateway Station I disembarked and, standing on the platform, watched as the train made its way west.
Follow New York Times Travel on Instagram and sign up for our Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2026.
The post In the Private Jet Age, the Quiet Allure of Private Rail appeared first on New York Times.
