Rolling Along

Sherrill Paul Witt's unique business put Cleveland on track.
During one of Lolly the Trolley’s trips through Cleveland’s Warehouse District, the vehicle turned a street corner only to be blocked by a Volkswagen. Someone had illegally parked the little car, which made it impossible to maneuver the trolley full of sightseers.

After a few minutes of waiting and assessing the situation, several physically fit, twenty-something-year-old tourists hopped off Lolly and gently moved the VW out of the way.

Trolley Tours of Cleveland’s co-founder and driver, Sherrill Paul Witt, was back on track.

Not all of the obstacles in Paul Witt’s life have been so easily surmounted. But the 60-year-old Sagamore Hills resident has no regrets about the business she and her former husband, Peter Paul, began in 1985. Lolly, a red gasoline-powered tour bus designed to look like a historic trolley, is a popular sight on the streets of Cleveland.

“Maybe when Lolly celebrates her 25th anniversary in two years, we’ll throw a big party and invite everyone who got us to the dance,” says Paul Witt, who graduated from Brecksville High School and earned a degree in journalism from Ohio Wesleyan University in Delaware, Ohio.
The idea for starting their business began 25 years ago when the entrepreneurial couple was visiting Boston, and saw a tour trolley zipping around the city’s streets. Already an experienced tour guide, Paul Witt was instantly intrigued and wanted to bring a similar opportunity to Cleveland.

But buying a trolley is not exactly like purchasing a family car: The cost of one trolley is equivalent to four luxury autos. And imagine telling lending companies that you want to start a tour company in Cleveland, back in the days before there was a Rock and Roll Hall of Fame and Museum, or a Tower City. Try suggesting that a trip down Euclid Avenue would be educational, even though at the time, scantily clad “strolling hostesses” (as Paul Witt calls the soliciting women) could be seen walking the sidewalks from the trolley.

“I don’t know many individuals who would travel to as many financial institutions and investors as Sherrill did –– I believe it was 300 –– when she first applied for financing in the mid-1980s, only to be refused time and time again,” says Christine Zust, president of Zust & Company, a strategic communications business and one of Paul Witt’s closest friends. “Yet, Sherrill proceeded to the next bank or angel investor undaunted.

“Eventually, she received the financing she needed to launch Trolley Tours of Cleveland. And thank goodness she did because it’s a tremendous asset to the city.”

Sen. George V. Voinovich, who served as mayor of Cleveland when Trolley Tours was launched, agrees. “[Sherrill and Peter] were co-founders of the company at a time when Cleveland’s renaissance was just beginning to take hold,” he recalls. “On trolley tours, they would point out the future home of our museums on the lake front, serving as great ambassadors to the community.”
Paul Witt still shudders when she remembers those early days of launching her business. She chose a tourist-trolley maker in Florida to design the first vehicle for her company. (The trolley is named Lolly in homage to a relative of one of the manufacturer’s employees.) Ten minutes before the trolley’s coming-out party for 700 friends, not-so-close friends and media, the guest of honor hadn’t arrived. Paul Witt frantically searched for some sign of the vehicle. Finally, she spied it rounding the corner. But it was a blue trolley –– not the red-and-green one she had ordered. It seems the company had sent a loaner. The driver spent three hours taking partygoers for spins around the block before heading back to Florida.

Paul Witt eventually received the trolley she had ordered, but it didn’t come with instructions. She learned to drive the 34-foot-long vehicle in an empty parking lot the day before tours started.

Today, the company employs 20 drivers, many of whom retired from other careers. Tours are one- or two-hours in length and explore a range of sites, including the West Side Market, University Circle and PlayhouseSquare. In addition to holding the commercial driver’s license necessary to drive Lolly, guides must be friendly and articulate about the city.

“Our attitude is: If you don’t love Cleveland, you shouldn’t be working for us,” Paul Witt says.

Cleveland is not San Francisco: There are no major hilly streets that trolleys must navigate. But like any business, Trolley Tours of Cleveland has had its share of ups and downs.

At one time, the company owned 15 trolleys, but due to a fluctuating economy, that number has been reduced to eight. And, since the trolleys get only five miles to the gallon of gas, it’s been necessary to slightly increase the cost of the tours to accommodate rising fuel prices. (Tickets for adults range from $10 to $17.)

But for many people, the memories are still a bargain. Over the years, Paul Witt estimates, Lolly has shown at least a million out-of-towners and locals the best of Cleveland. The trolley has carried students, prom dates, wedding parties –– Paul Witt estimates about 4,000 brides have hopped aboard –– and candidates of both political parties. The trolley, she adds, has also been part of too-many-to-count anniversary, retirement and birthday celebrations and this-is-your-life parties.

Lolly was there to help legendary producer, director and playwright George Abbott celebrate his 100th birthday at PlayhouseSquare in 1987. Actor Eddie Albert, along with Broadway composers Betty Comden and Adolph Green and a host of others, partied on Lolly that night and signed the trolley’s interior. (Unfortunately, a member of the cleaning crew saw the signatures afterward, thought it was graffiti and washed the autographs off.)

 “People come to us because they want a happy event to be even better,” says Paul Witt.

But there is one tour she wishes never would have happened. In 1989, one of the trolleys stalled on the Inner Belt and was rear-ended by a semi carrying massive rolls of steel. Lolly was pushed 400 feet, before coming to rest at the edge of the roadway. There were no fatalities, but the accident made national news.

“I don’t think we will ever put it behind us,” Paul Witt says. “Peter and I still get very emotional when we talk about it.

“But the most surprising part of it was that so many people from all over the United States who had ever taken our tours called us when they saw the accident on the news,” she adds. “They just wanted to know if Lolly was OK and how we were doing. It still makes me cry when I think about it.”

Throughout its history, Trolley Tours of Cleveland has had several offices in the Flats. Each has been on or near the former site of St. Mary’s on-the-Flats, the colloquial name of the parish Our Lady of the Lakes, which served as the first Catholic church in Cleveland.

“Peter and I sometimes think that perhaps this is special ground, and that we have been looked after all these years as we have worked to maintain an honest, courteous, and caring business,” she says.

Paul Witt adds that she firmly believes she’s “a very little thing in a vast cosmos that is part of certain bigger plans,” and agrees with the concept of serendipity and the notion that things happen for a reason.

Born in Canada, she learned at an early age to cope with life’s punches:Her father was killed in a car accident when Paul Witt was 6. She and her mother, Shirley Duncan, moved to Akron in order to be closer to relatives.

And although she calls her 1996 divorce “a very sad time” in her life, Paul Witt recognizes the marriage not as failure, but as change. She and Peter remain professional partners, and she acknowledges that her former husband “brings discipline and order to the business.

“Through maturity, I have learned you get a certain sense of yourself. Part of that maturity is accepting those things about yourself that aren’t good,” says Paul Witt, who claims she doesn’t delegate well, procrastinates and micro-manages, and can be shy in a roomful of strangers.
But Lolly’s co-owner also gives herself credit for being “imaginative, a people person and customer-service oriented.”

“Sherrill observes the world and people around her in a very caring way,” says Zust. “She takes nothing at face value. She always asks for clarification. I’ve seen her strike up conversations with strangers on many occasions because she was curious.”

Paul Witt’s love of learning has not diminished over the years. She takes Spanish lessons and is considering enrolling in a tap-dancing class. She also enjoys the company of her 87-year-old mother who lives nearby, and relishes time spent with her husband of seven years, financial adviser William C. Witt.

 “It was an honor to be asked to be one of Sherrill’s bridesmaids when she remarried,” says Jackie York, district development and marketing manager for PlayhouseSquare. “We were professional acquaintances before we became personal friends. I have great respect for Sherrill as a woman, as well as for what she and Peter accomplished years ago. It shows you what fortitude, desire and careful planning can get you. They have made a permanent statement in Cleveland.”

Because so much of her profession-al life revolves around interacting with people, Paul Witt considers her quiet home to be a sanctuary that helps her achieve balance. She tends a few robust tomato and chive plants in her enclosed back yard in warm weather, and welcomes cardinals and chickadees to her snow-covered patio in winter. She values the beauty of silence as much as the clang of a trolley bell.

And although Paul Witt says she’s too busy to think of the future right now, she admits that she doesn’t see herself sharing the helm of the business when she’s 80. Nothing would delight the entrepreneur more than to have someone who truly loves both Cleveland and Lolly buy Trolley Tours of Cleveland.

But that certainly won’t happen tomorrow, says Paul Witt.

“I’ll retire,” she adds, “only when it isn’t fun anymore.”

For more information about Trolley Tours of Cleveland, call (216) 771-4484 or visit
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