John Smith, Robby Smith and Jim Schellinger stand in front of a window cling celebrating 30 Years of Christmas Stroll. The Smiths and Schellinger were involved in early conversations about the event and continue to be involved to this day.

The story of the Sheridan County Chamber of Commerce’s Christmas Stroll is one of twinkling lights, festive music and visits with Santa in downtown Sheridan. But the story starts with none of that. In fact, it begins in complete and utter darkness.

On Black Friday 1993, John and Robby Smith were preparing for their first holiday season as owners of a downtown business. But as shoppers spent thousands of dollars in stores across the country, downtown Sheridan was dark and quiet.

“About 5:30 or 6 (p.m.), I looked down the street all the way to the end, and there wasn’t a soul on that street,” John Smith said. “And we made it til about 6:30 or 7, and I said ‘Let’s lock it up. We’re done.’ I was very upset…There was no business.”

The Smiths brought their dissatisfaction with them to the next meeting of the Chamber’s retail committee, where fellow member Jane Rice proposed a solution. Rice had just visited family in Bozeman and encountered a new event there known as a Christmas Stroll. “Maybe we ought to try it,” Rice suggested.

Fellow retail committee member Jim Schellinger remembered being excited about the idea from the start.

“People were all taking off for Billings and doing their Christmas shopping,” Schellinger said. “So when we were approached with the idea of putting the Stroll together, I was like ‘Heck yeah.’ It would be a way of keeping people here at least through that first weekend of the holiday season. If we can give people a reason to stay, that’s wonderful for our community.”

Rice’s brainchild quickly grew and evolved into an annual Sheridan County holiday tradition – one that has survived bad weather, global pandemics and numerous changes over the years to become a core holiday memory for generations of Sheridan residents.

“It’s like rodeo,” Robby Smith said. “It’s become this big social thing for people who are from here to connect with their friends from college or an old friend who is in town visiting their mom or dad or whatever. It’s so much more than just shopping now. It’s become a big reunion.”

The Chamber’s Christmas Stroll officially launched on Black Friday of 1996, although John Smith thinks there may have been some early “unofficial” versions of the event in 1994 and 1995. Schellinger said it was clear from the start the event was a success.

“I used to sit in those retail committee meetings, and it felt like it was a constant battle for everything,” Schellinger said. “It was hard to make any of them happy. But Christmas Stroll was the one thing that not one of them could complain about.”

John Smith agreed.

“It was a success, period,” John Smith said. “It was awful big right off the bat, and it just kept getting bigger every year.”

Since that inaugural event, it has been the role of the Chamber’s Christmas Stroll committee to continue that success, finding new ways to grow and expand while staying true to the event’s central mission: keeping shoppers in Sheridan and supporting local business, John Smith said.

“We want to keep it going, keep it fresh,” John Smith said. “While never losing sight of what the whole point of it is.”

The event has changed in countless ways over the years, from the purchase of new Christmas lights for Main Street to bringing in local grade school students to design the annual Stroll button, Robby Smith said. Two of the biggest and most successful changes have been the implementation of Get Caught Shopping and the expansion of Christmas Stroll to a day-long event.

In Get Caught Shopping, the Chamber’s elves catch individuals wearing their Stroll button while shopping local on Stroll day and on the weekends following Christmas Stroll, and reward those “caught” with Chamber Bucks. Robby Smith said this was a great way to keep the holiday celebration going all throughout the season.

“The Stroll is still the main thing but Get Caught Shopping kind of keeps people in the spirit every week,” Robby Smith said. “I think that was one of the best things we added, the Get Caught Shopping.”

Similarly, the expansion of Stroll to a daylong event has proven a great way to keep the Christmas spirit going for more than a few hours, Robby Smith said.

“That came about because of COVID,” Robby Smith said. “We used to just do it from 4 to 8 at night. But I really like the all-day because I think people do shop during the day so that they don’t have to pack things around at night.”

The Smiths and Schellinger remain involved in Christmas Stroll 30 years later, with Robby and Jim still active on the Christmas Stroll committee and John Smith sharing his thoughts on ways to evolve the event while staying true to its core mission. For Schellinger, the same passion that drove his participation in the event 30 years ago keeps him excited about Stroll all these years later.

“I still strongly believe in the fact that people need to shop local,” Schellinger said. “And the more we can do to make that happen, the more we all benefit. I really push that, and that’s why I stay involved as much as possible.”

The 30^th Annual Christmas Stroll will be held Friday, Nov. 28. The event will be dedicated to the memory of Jane Rice, who passed away earlier this year.