Lolly the Trolley is ending its run after almost four decades in Greater Cleveland.The Plain Dealer
CLEVELAND, Ohio – Next week, an era will roll to an official stop in Cleveland when Lolly the Trolley finishes its 37-year run in Greater Cleveland.
Owners Sherrill Paul Witt and Peter Paul are putting the brakes permanently on the trolley, which canvased Northeast Ohio streets and landmarks since April 15, 1985.
“It’s a combination of factors – certainly Covid was a contributing factor, and there has been a changing feel or changing landscape,” Witt said. “As time went on there have been changes in the insurance industry that are making it harder for us to hire and train our own people. Over the years, there have been increasing regulations from the city that were kind of burdensome.”
The trolleys have not been operating for the last year and a half or so, she said. But as of Tuesday, May 17, they will find new life, moving to Clearwater, Florida.
Lolly traveled as far south to the Kent and Canton areas, as far east as Ashtabula and Geneva, and as far west as Sandusky. No matter where the rolling ambassadors for Cleveland would go, they would bring a smile to the faces of passersby and passengers alike.
“That was really it,” she said. “People from all walks of life, people with abilities and disabilities, people who were rich, people who had nothing. Everybody could ride the trolley and they would smile.”
She said Lolly even carried wedding parties of some of the children of people who were married and sat aboard the trolley. Lolly was involved in more than 4,000 weddings over the years.
“It’s a memory you don’t forget,” Witt said. “And I think our ability to highlight Cleveland, to change people’s minds and to really, at the end of a tour, say ‘I never knew Cleveland was like this.’”
Before Covid, the trolleys could hold 38 people each. Spacing out those riders during the pandemic’s restrictions proved challenging, Witt said.
They had as many as 15 trolleys at one point but pared it to eight over the years. In almost four decades, about 150 people worked at Lolly the Trolley, which covered 3.1 million miles in its tenure.
They were rolling ambassadors for the city, offering vantages and sightseeing for visitors and residents. When Lolly started, the city looked much different: All three of the main downtown sports venues were not built. The Rock and Roll Hall of Fame wasn’t around, nor was its neighbor, the Great Lakes Science Center. Cleveland had zero craft breweries.
It rolled along with major events, sharing a bit of the national spotlight that shined during several Major League and NBA All-Star Games, several World Series, NBA Finals, Rock Hall inductions and more. Annually, Witt said, all eight trolleys were used for the St. Patrick’s Day Parade.
The moments will continue, without Lolly. And while the trolley will retire, so will Witt, who also credited her former husband and business partner for his work over the years.
“During Covid I got to find out what it was like to not work seven days a week,” she said. “I think it will be fun (where) I will be a tourist now and take somebody else’s tour.”
I am on cleveland.com’s life and culture team and cover food, beer, wine and sports-related topics. If you want to see my stories, here’s a directory on cleveland.com. Bill Wills of WTAM-1100 and I talk food and drink usually at 8:20 a.m. Thursday morning. Twitter: @mbona30.
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