This summer, one of the world’s most iconic road trips is beckoning thanks to a hotel prize giveaway worth thousands, but applicants will have to be family-minded to be in with a chance of winning the trip of a lifetime.
Route 66, stretching from Chicago to the California coast and one of America’s original highways, celebrates its 100th anniversary in 2026. To mark the occasion, Wyndham Hotels & Resorts is offering $20,000 (around €17,000) to hit the tarmac, but there’s one special condition: the winner will need to take a grandparent with them for the ride.
The intergenerational journey is being dubbed “The (Grand) Mother Road Trip” in a nod to a nickname for the historic road coined by US literary giant John Steinbeck, for whom the route served as a symbol of escape, transience, and new beginnings. In his masterpiece, The Grapes of Wrath, a poor family sets out together towards California in search of a happier future, encountering other voyagers and stories along the way. With seven nights at Wyndham properties, including Days Inn®, Super 8®, La Quinta®, Ramada®, and Howard Johnson® on offer, presumably the hospitality group is anticipating their competition will provide a family today with the same chance of shared adventures—hopefully with a happier ending.
“Route 66 is one of the most enduring symbols of American travel, and for decades, Wyndham’s iconic roadside brands have been part of that journey. As we celebrate its centennial, this incredible road trip brings that legacy to life, handing the keys to our open-road ambassadors for an unforgettable adventure that inspires travelers everywhere to hit the road, explore new destinations, and create lasting memories,” said Michael Shiwdin, GVP, Integrated Marketing, Loyalty & Digital, Wyndham Hotels & Resorts.
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To take part, applicants must be legal US residents of at least 18 years of age. The nominated driver must be 21 or older with a valid license. The competition does not discriminate against blended families or those who have suffered loss. Any grandparent figure can be recognised for the application, including step-grandparents and “chosen family,” Wyndham says, adding: “If they’ve played that role in your life, they count here.”
Being comfortable creating and sharing social media content is a must. Would-be participants will need to send Wyndham a short video or essay with a photo, explaining their “connection, sense of adventure, and why Route 66 was made for you.” For full details and conditions, see Wyndham’s reward page online.
