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Big Dipper owner standing outside the business

Decades of dedication: Big Dipper owner reflects on family legacy, growth, and whats next

Content originally posted in The Owensboro Times in May 2025. 

Robert Osborne never imagined hed spend nearly four decades behind a grill, but now, as the longtime owner of the Big Dipper, he cant imagine doing anything else.

Opened by his father George Osborne in 1954, the Big Dipper remains one of Owensboros most beloved roadside staples, offering oldfashioned hamburgers, pigs in a blanket, and ice cream all served from a modest building along West Parrish Avenue.

This business helped my dad put five kids through college and buy a farm, Osborne said in an interview from London, where he was vacationing while his son helped run the restaurant back home. From day one, it was good.

Osborne recounted a pivotal summer in 1981 when a storm severely damaged the building just as Parrish Avenue was being widened and a McDonalds was going up nearby. At the time, he was a junior at the University of Kentucky and home for the summer.

My dad was close to retiring he was more interested in farming but I helped him rebuild the roof, put up a new sign, and people kept driving by asking when wed reopen, Osborne said. Thats when I fell in love with the business.

He returned to college and later took a job in Denver, but the pull of the Dipper and a call from his dad saying, This business is unreal brought him home.

Its been a family effort ever since. Osbornes wife Terry handles the payroll and bookkeeping, and he still spends time behind the grill, even while looking for ways to modernize without losing the charm.

Youre always tweaking things if I can find a way to save my employees one step in a process, Ive done my job for the day, he said.

One of the biggest changes in recent years came with the addition of credit card processing, something Osborne resisted for years. That changed when Independence Bank offered to help set up a system with more affordable fees.

I was shocked how well its gone, he said. We hear it all the time people saying they didnt stop because they didnt have cash. Its made a huge difference.

Though Osborne remains firmly planted at the Dipper, hes also eyeing the future. Hes acquired additional property around the restaurant and is envisioning updates to the front façade, while trying to preserve the restaurants nostalgic feel.

Theres been some development around us, and were thinking about how to adapt, he said. But change is tricky our customers dont want us changing too much.

Even after 37 years, Osborne said hes in no rush to hand over the reins, although hes begun mentoring a new generation of employees.

Ive had people work for me for 20 to 25 years, and we had one lady who worked for the family for  nearly 50 years she came to our Christmas party at 92,” he said. You cant buy that kind of dedication.

When asked if his father ever imagined the Dipper becoming what it is today, Osborne answered simply, No. George Osborne only planned to sell soft serve, and even considered a Dairy Queen franchise before deciding to go independent.

That changed everything, Osborne said. He could do it his way no franchise fees, no rules. Just good food and hard work.

As for retirement?

I keep saying Im going to, but I dont know if I can, Osborne said. Ive been blessed. This place the people its still an inspiration.