From the moment Kelly Bennett walked into Oscar’s Cafe seven years ago, he knew the place was special. A local staple of Durango culture, he was in awe at the decor. With old Snowdown posters that decorated the walls like a yearbook tribute to Durango’s past and toy trains that chugged above the tables, he knew he wanted to be a part of it. Now, he and his business partner Guy Winzenread own the eatery.
Oscar’s started when Paula and Bruce Berg opened the diner 42 years ago and has steadily become a prominent spot in Durango’s restaurant scene. It is even said that before the internet, Oscar’s was where people went to discuss news around town. Business meetings, family outings and various social events all started with a meal at Oscar’s, and little has changed.
“It is the local bar without the alcohol in the morning,” Bennett said. “Deals get done. Lawyers come in and meet.”
Bennett and Winzenread have spent most of their careers working in restaurants. Before Oscar’s, Bennett worked for Golden Corral and Applebee’s, winning national awards with both restaurants. He also spent a few years working at Lone Spur Cafe running daily operations.
“I was working my butt off during COVID and that’s when I came to the revelation that if I’m going to work this hard, I might as well be doing it for myself,” he said.
Winzenread has spent the last year working at Purgatory Resort as the manager of the Durango Mountain Club, and before that worked in point-of-sale system repair for restaurants, as well as being a manager at Carver Brewing Co.
“Technical service stuff was really my bread and butter, but when COVID closed the restaurants I was looking around for a guaranteed income again,” he said.
Both pride themselves on being unselfish and understanding when it comes to their employees and paying a fair wage. Being from a restaurant background, they understand what it is like to work service jobs in Durango to make a living.
“I’d put our kitchen wages up against anybody in town,” Bennett said. “Our staff is superb at what they do and coming from where we come from, I know what we’re asking them to do every day. The vision for us is to have a family environment where people are paid very well to do a job where other people are trying to get by being paid $14 to $15 an hour. This is worth more than that to me.”
The two take pride in being an employer of choice in town and believe if they stay true to the values held through their restaurant experiences, it will create a positive workplace environment for service industry employees. However, this is not strictly an Oscar’s concept; the two have started what they call the 550 Food Group and hope to take their ideas to other establishments.
“Imagine being able to staff someone at one restaurant and if they are looking for work somewhere else, too, you can still put them somewhere else,” Winzenread said.
Both feel that being working owners help them see from the perspective of their employees and will further help them be exemplary leaders.
While minor upgrades have been made, the new ownership insists on keeping Oscar’s the same as it has always been. The restaurant’s biggest upgrade is the toy train that runs above the tables and bar of the diner. It was made specifically to resemble the Durango-to-Silverton train.
“Apparently, there are train magazines that tell people to come here (Oscar’s) because there’s a train running around, so we thought we’d embrace it,” Bennett said. “We’re making a lot of 20-year decisions right now, and that’s our marketing over the next couple of years. I could advertise in a newspaper or radio and I wouldn’t get as much back as I did with that train.”
The only other major change to the restaurant was the name of the French toast. The new owners renamed it to pay homage to one of the former owners, Bruce Berg, who recently died.
“We haven’t made any changes that should affect the overall guest experience,” Winzenread said. “We didn’t want Oscar’s to change and we figured nobody really wants us to change.”
While there have been many questions about introducing alcohol to the menu at Oscar’s, the new ownership wants to maintain the values placed by the previous owners and do not want to make drastic changes.
“People ask if we are going to start serving mimosas and bloody marys. No, that’s not the plan,” Winzenread said. “That’s a big change to the place and we’re not trying to do that.”
This summer, the diner will have different hours from Memorial Day to Labor Day. For those riding the train in the morning, Bennett wants to open at 6:30 a.m., but the hours have not been finalized.
They said it would create a better experience for tourists and locals.
“We’ll probably open at 6 or 6:30, definitely 6:30, we’ll see about 6. For nothing more than to capture the train crowd, so our locals can still get their consistent experience,” Bennett said. “We don’t want to be clogged up with so many tourists that the locals can’t even get in because this is the locals’ place.”
The duo had a ribbon-cutting April 19 to signify the change in ownership.
