Best known for its burgers, fries, and milkshakes, Frosty’s Drive-in has been a town favorite and loved by travelers for decades. The quaint pink building in the heart of St. Regis was at one time a postal office, before becoming the quick pitstop for grub and ice cream.

Originally the restaurant was owned and operated by Rick and Pauline Jasper, later being ran by their son Kenny Jasper.

Kenny said, “My parents purchased the St. Regis Camp property in 1976. The first few years the building was the post office in town. In the late '70s the post office moved to its current location and my parents changed it to the Frosty Drive-in.”

The pink and black retro dining establishment is starting a new chapter under new management and likewise a new name. Frosty’s is now Winki’s Diner.

Under the helm of longtime St. Regis resident Syleena Simkins, she is taking her expertise in the food service industry and overhauling the old drive-in.

What’s a Winki, you might ask? Simkins laughed, “My two uncles Bud and Ben Simkins called me Winki when I was a child. I hated the name when I was young, but through the years I grew to love it. My children helped me decide on the name as well.”

Simkins was born in Superior and even worked as a teenager at Frosty’s Drive-in taking orders and handing out soft serves. After graduating high school, she moved to Missoula and garnered work experience in several different food and bar establishments.

Simkins noted, “I managed the Uptown Diner for some time and managed the Missoula Osprey concessions for a few years. I enjoy food service and have been in the industry since 1993. It’s nice doing something that you can enjoy.”

Since taking over the Super 8 Motel for his mother after her retirement, and running several other businesses in town, Kenny Jasper recognized that he was feeling stretched thin. In regards to Frosty’s he shared, “Over the last couple of years I came to realize I didn't have the time to run it properly. I then approached Syleena about leasing the building from us.”

For Simkins the business proposal was a dream come true. She admitted “I didn’t really think it would happen so suddenly, but I think it’s meant to be.”

With her history in food service and management, Frosty’s is in good hands. Kenny expressed, “She's a great fit with her background in the restaurant business and the skill set she has.”

Simkins expressed, “I thank Ken for giving me this opportunity to lease the building and I’ll do the best that I can to improve the restaurant and make customers happy.” She also added, “I have several children that attend school here and I plan on raising them here in this community. So why not do what I love, love what I do and where I do it.”

Currently the large faded pink Frosty’s sign still greets customers but Simkins is in the process of changing things inside and out.

She explained, “We are getting new signage and logos made and put up very soon. The menu is being updated, some items are going away, some are staying, new items will be featured as well.” But rest assured the most treasured item on the menu will remain; ice cream. Whether it’s a classic cone, decadent sundae, or flavorful milkshake, you can still count on Winki’s Diner to satisfy your sweet tooth. Simkins added, “We are throwing around the idea of drive thru breakfast but not sure if there is a demand for that sort of thing around here.”

The diner’s theme and décor will still have a retro 1950s vibe. Simkin’s will be using bodies of classic cars outside the building for patrons to dine in. Car hoods will be repurposed to display Winki’s new menus items. And the color scheme incorporate a flashy new red to paint over the old pink.

Simkins lease officially started at the first of the year, since then she’s replaced one of the fryers and some of the kitchen equipment. They have done a lot work to be more power efficient and eco-friendly.

Updates to the kitchen supplies and putting systems in place for the busy summer season are Simkins current focus. She stated, “This place is going to get a new paint job as soon as the weather permits. We are planning a kitchen remodel and new kitchen floors sometime before Memorial Day.”

As Simkins gears up for her first busy tourist season running Winki’s Diner in St. Regis, Kenny Jasper also reflects back on the establishments transition. He conveyed, “I'm sure in some ways I’ll miss it, but change is good and I think Syleena will brighten the future of St Regis way more than the loss of the Frosty’s.”

Like most adolescents can fondly recall getting that ice cream cone to sit just right and learning to count back change was how they earned their first pay checks.

Simkins hopes to keep that tradition alive. “I want to train high school students to be hard workers with good work ethics, and train them to be responsible, reliable employees of the future.”

Winki’s Diner is currently open for business and will have longer hours from Memorial Day to Labor Day each year. The official grand opening is slated for April 1.

Simkins recommended that folks stop in and see what’s new in the coming months.

“Change is good in some cases, come by and see for yourself. If you’re in a hurry or don’t want to get out of your pajamas call your orders in to 406-649-9753, or swing by the drive thru and pick your order up.”