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Upon meeting Raymond H. Carr, his first move is to hop into a car—in this case, a 2004 black Cadillac Escalade—and go for a ride. Heading down his steep driveway from atop a hill in Chester Springs, he departs for another of his homes. It’s a four- or five-minute trip, “depending on traffic,” he jests.

All the while, he’s promising that his Pickering Hollow Farm won’t be comfortable. It’s largely vacant except for his other cars in two garages.

Carr could very well be the Main Line’s modern-day Jay Gatsby. He has the automotive fleet—16 in all—to support the comparison, along with the rags-to-riches story. He’s the commercial real estate developer who made once-dry Uwchlan Township wet.

More than anything, he says, it’s the automobile that’s the symbol of the American Dream. “It’s a vehicle,” he says. “It’s a time machine to a degree, in that it moves you from place to place. It moves your emotions, too. It truly does. And around each corner, there’s a different landscape—and an opportunity.”

Carr would know. It’s how he’s lived his life—on one long, obsessive drive, with different turns, uphill and downhill. Still, he’s the first to say it’s better to chug along at a steady pace—say, 18 mph, like he commonly does in his midnight-blue 1912 Baker Electric, with its creamy, yellow wooden-spoke wheels.

In 1995, at age 70, he covered 3,303 miles from Astoria, Ore., to Atlantic City, N.J., in 33 days. He passed through 260 cities and towns in 14 states. He covered an average of 101 miles a day, exiting the Pennsylvania Turnpike July 4 on his way home to visit then-Gov. Tom Ridge, who named him Pennsylvania’s goodwill ambassador to the world. Carr gave his friend and political kindred a ride through downtown Harrisburg in his open-air car.

“The governor’s secret service men were up in arms,” he says. “But he loved it—and so did I.”

At 83, Carr hasn’t slowed down. In fact, he’s organizing his next one-man motorcade. Depending on the new technology in batteries and charging systems, by September or October he’ll depart from the west coast of Australia at Perth and travel some 2,800 miles to Sydney on the east coast in his Baker Electric.

This transcontinental trip has long-range significance. He wants to prove that modern electric cars aren’t just environmentally friendly, but practical, too. His trip could even herald the future of 21st-century motoring.

“There’s a mission,” says Carr, like the unabashed dreamer he’s been called. “We’re working on recharging the battery in 10 minutes. If so, then you could plug in at a service station the same way you fuel up at a service station today.”

His Baker Electric is the type of battery-powered automobile that was popular during the first two decades of the last century. Powered by 12 6-volt lead-acid batteries, the only sound it makes is a slight hum. With its buggy-style folding top, it looks like a horseless carriage of old.

A bit old-fashioned, with a stubborn drive and a polished boyhood curiosity, Carr is an incurable romantic. He’s as deeply in love with America’s past as he is with the technological future.

Last Dec. 1, he married for the third time. He met his new wife, Bonnie Carr, at Philadelphia International Airport, flying her in from Michigan on a blind date a niece had arranged. He gave her a tour of Lancaster County in his 2004 merlot Thunderbird. “Later, I found out she spent a lot of time and money getting her hair done,” recalls Carr, who has 13 grandchildren and 11 great-grandchildren. “She meets me, and the first thing we do is get into a convertible.”

After covering scenic Route 30, the two visited Longwood Gardens. The next morning, he took Bonnie, 65, to church in a classic 1926 Pierce-Arrow once owned by his father. After that, it was brunch at the Kimberton Inn.

“I was really pouring it on,” he admits. “You have to think young. I don’t mean you want to be in diapers again, but Bonnie and I, we still dance. I still go into the office every day—even if it’s now only across the parking lot [at home].”

By design, Carr has downsized considerably, though he’d rather call it consolidation—and never retirement. He remains chairman and president of his flagship Cignature Hospitality Ltd. His resume includes more than 60 businesses, though he’s reduced his holdings to two main interests: automobiles and travel.

He’s sold his five hotels (four Holiday Inns and a Hampton Inn) and his restaurants, including the Kennedy-Supplee Mansion in Valley Forge National Historical Park, the Duling-Kurtz House and Country Inn in Exton, Vickers Tavern in Lionville and the Stottsville Inn in Pomeroy. Four years ago, he also sold his most controversial venture: 4,200 acres in Berks County—3,800 of which he turned into a new borough, New Morgan, after fighting the outlying neighbors all the way to the U.S. Supreme Court, which wouldn’t hear the case. The founder remains the mortgagee on the tract.

Carr originally envisioned creating one of the major tourist and conference centers on the East Coast, which would’ve included a Victorian village, a 1,000-room hotel and an 18-hole golf course. He ended up building just a handful of homes and Thousand Oaks Industrial Park. And there was Carr Recreation Park, with its miles of natural trails and paved roads around a 300-acre lake, which opened in 1994. It has since been closed by the new owners, who are planning a new 12,000-unit residential development called Bryn Eyre.

“It wasn’t a downhill,” Carr says. “It was a major accomplishment. It took 6 1/2 years, but we prevailed. It took a lot of energy, was controversial and created bad publicity, but I don’t know anyone else who has created their own municipality. Do you?”

But it’s Carr’s abiding attraction to the automobile and its role in history—and his three Guinness Book of World Records citations for transcontinental travel in antique vehicles—that are his true passions.

Maybe Carr has done it for fun, and maybe because he’s had the time and means. But he’s never made a trip to prove he’s “different or better,” he says.

In 1993, a year before he covered the continent in the oldest electric car ever to do so, Raymond Carr drove the oldest car ever to cross the country. It was a one-cylinder, five-horsepower, gasoline-powered 1902 Northern runabout named “Chuffie.” The 2,489-mile tour began in San Diego and ended in Jekyll Island, Ga.

In 1996, on the 100th anniversary of the modern automobile, Carr’s 1909 Stanley Steamer became the oldest of its kind ever driven coast to coast. When Carr completed the ride from Alaska to Maine, he became the only person in history to span the continent in each of the three types of automobiles—gasoline, electric and steam.

Then, in 1997, he hit the road again, tackling his 10,241-mile Peking-to-Paris Motor Challenge. He traveled across 13 countries in 43 days in a 1939 Ford. In 2000, at the age of 75, Carr was at it again, motoring around the world in 80 days in the same 1939 Ford, beginning and ending in London. His 2003 African Safari Challenge took him across seven provinces of South Africa in a 1939 Chrysler. For 2004’s Moroccan Challenge, it was a 1957 Mercedes.

“Some of it, I guess, is associated with my name. But I also love driving—always have,” says Carr. “Plus, it’s the challenge of adventure. I think that was born in my soul.”

As such, Carr still has goals, one of which is to visit every presidential library or museum home in the country. So far, he’s only been to Truman’s in Independence, Mo.

“I just love the history of this incredible country,” says Carr, who’s wearing a blue blazer with an American flag pin in his lapel. “It is incredible—no matter what anyone says. I’ve traveled to Third World countries, and that’s when you realize how important it is to keep America strong and independent. I’ve been through southern Russia, and it’s pathetic. Socialism doesn’t work. Capitalism is what works for America. It’s worked for me.”

Carr was an entrepreneur even in high school. He formed his own orchestra in 1942. For the next two decades, outside of his military service years in World War II, he built the Ray Carr Orchestra into a popular act. While managing the group, he also worked 18 years in his father’s milk-trucking business, Robert H. Carr & Sons (there were five, plus a daughter). It provided the setting for his first automotive experience—sitting on fenders, holding trouble lights and handing mechanics tools.

Carr was born in Chester, where his father’s business began in 1931. The family and business moved to Exton, then Downingtown, and ultimately to Route 30 in Frazer. A 1943 Tredyffrin-Easttown High School graduate, Carr never went to college.

Uncertain what he’d do with his life, Carr left the family business after his father’s death in 1963. “I had five kids (with his first wife), no education and no money,” he remembers.

Then Carr read a book, William Nickerson’s How I Turned $1,000 into Five Million in My Spare Time, “and followed it to a degree.” He passed a six-night crash course and entered the real estate field in 1964. He began selling income-producing properties on the outskirts of Philadelphia. But like a guy in a car, he needed to get into the fast lane. Huddling with friends in his basement, Carr and the others questioned one another and stuck pins in a map. “All the pins seemed to be at the Downingtown exchange of the turnpike,” Carr says. “This was 1965. I went looking and found one [for-sale] sign covered up in the weeds.”

He borrowed $1,000 to secure an option on that 180-acre tract in Lionville, then formed a syndicate—at $35,000 a piece—to close the deal and develop the site. With then-partner Dave Knauer, he turned it into Pickering Creek Industrial Park. The two didn’t take a salary ($100 a week) until January 1969.

At the time, Route 100 was two lanes. Uwchlan Township was dry. Carr wanted to buy his first Holiday Inn, but he needed a liquor license first. At his insistence, a referendum vote made the ballot. One of two licenses went to Carr at Vickers, a farmhouse he converted into a tavern.

“I’ve always proved people wrong,” Carr says. “I had faith—religious and internal. If you don’t know you can, then you can’t. It’s like when I take a trip, I don’t ever think I can’t make it. It’s not cocky; it’s confidence. If you’re afraid, then you can’t make it.”

In his Northern, he feels free. In his Escalade, he feels safe. As for his 2004 Thunderbird convertible, “that’s just fun,” he says.

Carr does have another goal: He’d like to travel into space, though not in one of his antique autos. A space shuttle—another “time machine”—would do.

“Am I too old?” he poses. “I don’t think so.”

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