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End of an era: Looking back at the history of Lolly the Trolley in Cleveland

For 37 years, Lolly the Trolley helped millions get to know Cleveland on its tours, while creating memories that last a lifetime.

CLEVELAND — The date was April 13, 1985. It was Opening Day for the Cleveland Indians at Municipal Stadium, but also the day that Sherill Witt and her business partner Peter Paul got their first trolley.

It was the evolution of a business she'd started years prior. 

"We did walking tours," Whitt recalls. "And we provided guides to get on buses to do tours of Cleveland for groups."

At that time, Witt didn't know her business would educate people about Cleveland for decades to come, while being cemented in their memories forever. 

"So we’ve been part of people’s lives. And to give people that much happiness. And to give them good memories, is really what we’re all about," she adds.

Lolly the Trolley has transported about 2.5 million people around Cleveland over the past 37 years. Witt has archived some of those stories, pinning them to a bulletin board. They include thank you notes from people who got married on the trolley, as well as visitors who simply appreciated learning more about Cleveland and its history.

Witt's favorite memories? "The parades especially. And also doing the school kids and having them come into downtown Cleveland. A lot of parents won’t bring their kids downtown," she says.

WATCH: 3News' Stephanie Haney talked to several Northeast Ohioans about their memories of Lolly the Trolley

Riding the trolley was always a learning experience. But just like many other things, the trolley came to a screeching halt with the pandemic. The busienss survived, but it hasn't been the same. That led Witt and her partner to decide to call it quits, which wasn't an easy call. 

"Saying goodbye to all the people we’ve known forever, and having to tell all of my favorite customers that we cant do anything for them again. And I’m just going to miss everybody," Witt says.

The trolleys will find a new home with a tour company in Clearwater, Florida after 37 years of serving Cleveland well. Witt says she has no regrets. 

"We did the best we could for the city we love. And I think the city is appreciative."

As far as what's in the future for Sherill Witt? She says she wants to stay connected to tourism, but also wants to travel more. But no matter what she does, she knows she’ll have to make a trip downtown once a week, even though she not required to for work anymore.

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