article by anna rogers | photos by renata haidle

Maybe you’ve been gifted a sweet stack with the recognizable blue and white windmill label, wrapped to display the golden goodness inside through the packaging. Perhaps you’ve treated yourself to lunch or a pastry at the café on 17th Street West, stepping into the cozy space that feels like home, part of the neighborhood since 1987. Maybe you’ve popped in for a pie or cheesecake to carry out and elevate your holiday gatherings or celebrations. Whatever way you’ve encountered Caramel Cookie Waffles, it’s sure to have been a treat.  

Steeped in Tradition 

Dutch-born Jan Boogman and his wife Judy, a Montana native, met through their love of track and field, but they built their life on artisan cookies and good food. What started as a passion for bringing the taste of Dutch cookies to Montana in a concession trailer evolved into a beautiful, delicious legacy. Opening a storefront café in 1987 to share baked goods, soups, sandwiches, and more alongside their signature stroopwafel, they dedicated their lives to making Caramel Cookie Waffles what it is today.  

Longevity was always the goal for Caramel Cookie Waffles. The Boogmans prioritized consistency and quality and maintained a strong commitment to employee and customer satisfaction. The café became a neighborhood staple, with the Boogmans riding their bikes to work, many employees walking to work, and staff familiarity with its patrons. Over 35 years and countless hours of cookie-making later, Jan and Judy are enjoying retirement and have passed on the torch of this unique Billing locale.  

Thanks to a knowledgeable, dedicated staff, it’s been a seamless transition for those in Billings who love to frequent the café and munch on its cookies. Everything the Boogmans worked tirelessly and passionately to create remains: a family environment with a heart for community, good food, and the joy of a perfectly caramelized stroopwafel.   

Stroopwafel Scoop 

The stroopwafel is one of the most popular cookies in the Netherlands – one that was a staple of Jan’s childhood and has now become a staple in Montana. The sweet waffle cookies are sold all across the state in locally owned, mom-and-pop shops just like Caramel Cookie Waffles.  

This affordable and delicious treat is made by pressing vanilla and cinnamon dough between gas flame-heated waffle irons. The thin cookies are then split in two, filled with a rich homemade butter caramel, and put back together to bring you the perfect combination of sweet flavors and textures. 

What sets this local cookie apart from others? Caramel Cookie Waffles are small batch, made locally by a sister duo and their team in Billings. Sam and Dova worked with Jan and have become masters of the stroopwafel, sticking 100% to the traditional Dutch cookie-making method. The experts at Caramel Cookie Waffles hand caramel and hand package every cookie. Each blue and white bundle is made with care, love, and quality control.   

Continuing the Legacy 

The new owners’ goal is still longevity – continuing the tradition of care and love going into every cookie, bowl of soup, and baked good that changes hands in the café – and the dedicated employees are making this longevity possible. Many of them have been with Caramel Cookie Waffles for years, or even decades – a thread of continuity almost unheard of in today’s restaurant business.  

Café manager Sarah attributes her commitment to those she interacts with on the job. “Really, what kept me here is the customer clientele & the co-workers.” The camaraderie of a dedicated team and friendly customers who become friends is the atmosphere Caramel Cookie Waffles has always sought to create. 

With the influential guidance of Jan and Judy, an all-star team of employees, and new owners dedicated to continuing the lasting legacy already created, the Billings and surrounding communities can continue enjoying Caramel Cookie Waffles café and cookies as they have for nearly four decades. 

Sarah perfectly sums up the place and people with whom she spends her days: “It’s a unique staple – the hidden gem of Billings.” 

Originally printed in the February 2024 issue of Simply Local Magazine

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