Bob’s Diner & Bakery: 2025 Spirit of Wyoming Award Winner

Robert and Deanna Skillman

Nestled in Greybull, Wyoming, Bob’s Diner & Bakery, owned by Robert and Deanna Skillman, is a great spot for a homemade batch of biscuits and gravy, a fresh-baked dessert, and a large mug of coffee. The diner also boasts a renowned breakfast challenge and selection of homemade jams and jellies. But Bob’s Diner, and the family behind it, are responsible for much more than offering savory eats – their business has become an important part of the town of Greybull. To recognize the commitment to their business and community, Robert, Deanna, and Bob’s Diner & Bakery have been selected as the winners of the 2025 Spirit of Wyoming Award.

Robert and Deanna forged the dream of Bob’s Diner from unique backgrounds. Robert, immersed in the bustling atmosphere of his parents’ restaurant from a young age, learned the nuances of food service and the importance of hospitality. Deanna, raised amidst the steadfast values of ranch life and inspired by her mother’s passion for baking, harbored a lifelong aspiration of owning her own bakery. In 2020, Bob’s Diner & Bakery opened its doors.

The Wyoming SBDC Network assisted in the diner’s formative stages, providing guidance and expertise in a variety of areas. “The Wyoming SBDC was invaluable, helping us with everything from legal structure to financial planning,” Deanna says. “(Regional Director) Devan Costa-Cargill works hard to keep us in the loop about small business opportunities that we normally would not see. (The SBDC) really helped us understand our revenue needs, which was critical for a successful start.” This support helped in the purchase of their building and the adjacent property, which now serves as both a source of lease income and a community arts space.

Bob’s Diner & Bakery has become a place where the community gathers to celebrate, support, and connect. The diner has hosted charity events, the Big Horn County Arts Guild, and has a wall showcasing the talents of local artists. Robert and Deanna also support organizations like 4H, FFA, and the Annual Firefighters Dinner. Recently, Bob’s Diner & Bakery launched a monthly Open Mic Night, raising funds for local families facing medical crises. Robert is also involved in the Greybull Chamber of Commerce and stresses the importance of the family’s commitment to the town’s economic vitality. “Beyond the charities,” Robert says, “We want to see our community grow in a positive way.”

Last year, Bob’s diner was featured on America’s Best Restaurants – an event that brought the community together for a celebratory watch party. “It’s just a neat place to be,” says regular Charlie Baumer. “They’re always fresh and you just come down and have coffee and a cookie. You can talk about anything and everything.”

The Skillman’s resilience has been tested by profound personal challenges, particularly their son Ayden’s heart transplant journey. Balancing the demands of running a thriving business with the emotional and logistical complexities of supporting a child facing a critical medical situation was immense. Despite these hardships, the family and diner have persevered, overcoming challenges and continuing to evolve and grow.

Bob’s Diner & Bakery embodies the essence of Wyoming’s spirit. Through their unwavering dedication to community, resilience in the face of adversity, and commitment to serving quality food in a hospitable place, Robert and Deanna have created something special. Their generosity and commitment to Bob’s Diner & Bakery make them deserving recipients of the 2025 Spirit of Wyoming Award, recognizing the profound and lasting impact they have had in the lives of others.

https://www.bobsdinerandbakery.com/