Over the past decade, Clarence Russell has been showcasing the best of Winona with his bright red trolley.

But this spring, after years of birthday parties and weddings and hundreds of city tours, the trolley hit the end of the line. The financial burden of keeping it running simply became too much, Russell said.

“It’s been one of the hardest things I’ve had to do,” the 80-year-old said of the decision to stop giving tours. “I did the best I could to find someone to help me, but I couldn’t find anyone.”

To many in the scenic Mississippi River town of 27,000 residents, not seeing Russell and his trolley (he actually has two trolley buses, keeping one as a backup) running along the city’s streets will be strange.

“It’ll be a loss, absolutely,” Mayor Mark Peterson said.

For Russell, the trolley tours were more than a chance to boast about the town he’s called home the past 60 years. They were an opportunity to tell riders about Winona’s history and museums while also showing off its scenic beauty from high atop the Garvin Heights lookout.

“I felt like I was doing something good for the city,” said Russell, who retired as superintendent of the Woodlawn Cemetery in Winona 15 years ago.

Russell’s involvement with the trolley dates to 2006, when his friend, Don Trester, purchased a trolley bus online from an outlet mall near the Twin Cities with hopes of boosting tourism. Trester recruited Russell to help get the trolley to Winona, where it could be restored. A new engine was needed, along with a refinishing of the seats, floor and ceiling.

Before work was done, however, Trester suffered a stroke. He died days later, before having a chance to fulfill his dream.

Enter Russell.

By 2009, he had purchased the trolley from Trester’s estate and, with help from some of Trester’s friends, finished restoration. In honor of Trester, he named it the “Trester Trolley.” Later, he purchased a second trolley.

Over time, the sight and sound of the trolley — Russell always played music, including Christmas carols during holiday season — became part of the fabric of the city. Russell ran it seven days a week, offering tours on weekends or for special occasions, such as weddings and birthday parties.

But in recent years, ridership declined, and the cost of maintaining the trolley’s certification, licensing and insurance grew.

Bad luck struck, too.

In August 2016, while hosting a wedding party, one of the trolley buses caught fire. No one was hurt, but the damage was significant. Community members started a fundraiser to help pay for repairs, but Russell eventually was forced to take out a loan to buy another backup trolley, which pushed his monthly payments into the thousands of dollars.

Last December, he wound up canceling about half of his once-popular holiday lights tour, which used to sell out in advance. “People just weren’t signing up,” he said.

Figuring it would cost $6,000 to $7,000 to run the trolley another season, Russell decided to call it quits. He’s tried to sell the two trolley buses, but so far hasn’t had much luck.

Still, the memories are good ones, he said.

Even as business slumped, Russell never refused to give a tour, even if it was for just a party of two. To him, the opportunity to show off his city and see the joy in the faces of riders was what it was all about. Among his favorite memories — seeing youngsters light up when they heard the trolley coming their way.

“I’d see little ones 7 or 8 years old waiting a block-and-a-half away to wave at me,” he said. “They knew it was the trolley.”


David Mullen is a University of Minnesota student on assignment for the Star Tribune.