The Cannonball’s Heyday: Riding In Style On The LIRR

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Oh, the “Mad Men” days of Dashing Dan, who’d hustle to work on the Long Island Rail Road’s commuter line, then trade his suit for a breechcloth and head to eastern Long Island when the work week was over.

Settled in plush parlor seats with antimacassars, travelers like Dan conversed and sipped drinks served by attendants in white jackets as the Friday train sped east in an express run from Jamaica to Westhampton, making stops along the South Fork leading to Montauk. The passengers’ railroad mascot was “the Weekend Chief,” and Dashing Dan and Dottie were their workday counterparts.

“Cannonball,” said the drumhead on the last car’s observation deck. “Sundowner,” it said on the return trip west at the end of the weekend.

“I used to love to ride on that train on the rear end; it was nice and cool,” said Ron Ziel, who lived in Bridgehampton and Water Mill, of the Cannonball’s observation deck.

When the LIRR launches its first Cannonball express service from Manhattan this Friday, it will be tough to match the glory days of the Route of the Weekend Chief, even with special reserved seats where attendants serve refreshments in two cars. The ’50s and ’60s were an era when the Cannonball not only shuttled ad men, but also was glorified by them and by publicists and columnists like Robert Sylvester of the Daily News.

“Reader, take heed of the Cannonball. It was and is the class train of the LIRR,” he wrote around 1970. “Ah, memory! Ah, nostalgia! Ah, Wally McNamara who took all us Friday to Sunday tourists by the hand and showed us how to be beautiful people even if our names are not Capote or Onassis.”

“It was a very prestigious way to arrive in the Hamptons,” said JoAnn Morse of Montauk, whose father, the aforementioned Walter F. McNamara, came aboard the LIRR in 1957 to expand its summer parlor car service. He bought up used luxury cars from the Pennsylvania and other railroads as well as privately owned cars. The railroad’s director of special services, Mr. McNamara introduced beverage carts, bar cars and the Clamdigger cocktail of vodka and Clamato.

“To drive your Mercedes out to the Hamptons was cool, but it was even cooler to come out on the Cannonball,” Mr. Ziel said, who’s published a number of books on railroad history.

“There were a lot of very famous people, writers and people that were in film,” Ms. Morse said. “The interesting people that rode the train—you never knew, it could be Frank Sinatra.” The railroad reserved a car, often with an Indian place name, in case someone important wanted to use it at the last minute, and people bought season tickets for the deluxe accommodations. Strangers got to know each other through their pilgrimages out east, Ms. Morse recalled. Dinner was served on linen tablecloths at one point.

“We used to say, ‘Three martinis to Speonk,’” Ms. Morse said. An old cartoon in the Daily News shows two women watching their besotted, besuited husbands stumbling off the train. “He wrote about the men’s wives being angry,” Ms. Morse said of the accompanying column by Mr. Sylvester, who was a good friend of her father and also lived in Montauk, “because the husbands were three sheets to the wind by the time they got to East Hampton.” The wives, of course, had been stuck in the country with the children all week.

“It was the time of the three-martini lunch … when they actually had a bar in the office,” Ms. Morse said.

“That was a luxury form of travel, so some of them were amazing because the interior [had] some really fine, crafted woods and … really nice cabinetry,” she said.

She wasn’t certain that they were used for the Cannonball, but some cars had hollow walls dating from their bootlegger days, with secret cabinets that would indicate how many cases of liquor they could hold. Some cars had a dining room and a drawing room.

“Parlor cars, like copper lustre ware, were a lost art,” Mr. Sylvester wrote around 1970. “Not to our Wally. … He found a parlor car which had a ‘speaking platform, I do believe Gen. Grant addressed the populace from the platform. He found a parlor car which had only staterooms, and the most sought-after of these staterooms had nothing in it but a feather bed.”

The Cannonball was the last train to have that open platform, and it was the last all-parlor-car train in the country, according to Mr. Ziel, who now lives in Tucson, Arizona.

The Metropolitan Transportation Authority took over the railroad in 1966. Coaches were added to previously all-parlor-car trains, according to an article in Keystone, a publication affiliated with the historical society of the Pennsylvania Railroad, and the introduction of federal and state funding began to make offering fancy parlor service to the Hamptons seem discriminatory.

Having made its first run to Montauk from Jamaica in the 1890s, the Cannonball is the only named train still operated by the LIRR today.

In these 21st-century days without porters, a direct route from Manhattan may well prove tempting to the Mad Men of today. The railroad’s president, Helena E. Williams, has pointed out that the Pennsylvania Station departure eliminates the need to change trains with baggage from Jamaica.

A far cry from the headdress-wearing Weekend Chief, the Cannonball’s new logo is a more serene picture of the Montauk Lighthouse.

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