Title: Owner
Workplace: The Starboard Restaurant and Bethany Blues
Alma Mater: Randolph Macon College
Boards: County Bank, Dewey Business Partnership, Rehoboth Beach-Dewey Beach Chamber of Commerce, Delaware Restaurant Association
What is your toughest challenge? “Trying to stay 27 years old… I’ve been struggling to stay that age.”
When it comes to working your way up in a business, The Starboard’s Steve “Monty” Montgomery knows exactly how it’s done. Over the decades, he has worked his way up in the local restaurant and business world, where he’s also helped host hugely impactful community events like the annual Dewey Goes Pink 5K, in support of the fight against breast cancer, and the annual Running of the Bull that’s attracted Hollywood stars like Ryan Phillipe. From working the door to running the show, Montgomery has expanded from working at The Starboard to running several of the most-popular restaurants at the Delaware beaches.
Received the award in 2024 and 2025.
