Forget the typical summer getaway. Wyndham Hotels & Resorts is dangling something far more meaningful than your average hotel voucher: a fully funded cross-country road trip worth $20,000, complete with seven nights of accommodation across their brands. The catch? You've got to pack a grandparent in the passenger seat.
The prize celebrates Route 66's centennial in 2026, that storied stretch of asphalt connecting Chicago to California. For more than a century, this highway has represented pure American wanderlust, and Wyndham is betting that sharing it with a grandparent transforms a road trip into something genuinely unforgettable. They're calling it "The (Grand) Mother Road Trip," a clever nod to John Steinbeck's nickname for the route. In The Grapes of Wrath, families chased hope westward, and Wyndham seems to want modern travelers doing something similar, except hopefully with better luck.
Who Can Enter and What You'll Get
To qualify, you need to be a US resident aged 18 or older with a valid driver's license holder who's at least 21. The beauty here is flexibility: your grandparent doesn't have to be biologically related. Step-grandparents, in-laws, or anyone who's played that role in your life counts. Wyndham explicitly welcomes blended families and those who've experienced loss, recognizing that family takes many forms.
Winners will stay at Days Inn, Super 8, La Quinta, Ramada, and Howard Johnson properties along the route. That's seven nights of comfort breaks scattered across one of America's most scenic drives, turning pit stops into proper resting points instead of rushed parking lot naps.
How to Enter the Competition
This isn't a passive lottery. Wyndham wants to hear your story. Applicants must create a short video or submit a written essay paired with a photograph, explaining your connection to Route 66 and why this particular road trip matters to you. They want to understand your sense of adventure, your relationship with the grandparent joining you, and what makes this journey feel essential rather than just another vacation.
Social media comfort is non-negotiable. Winners will need to document their trip and share it, becoming ambassadors for open-road travel and intergenerational adventure. If you're camera-shy, this competition probably isn't your ticket.
The Route 66 Factor
Route 66 isn't just a highway; it's mythology wrapped in asphalt. The road winds through eight states, passing ghost towns, vintage diners, neon signs from another era, and landscapes that shift from urban grit to desert vastness. Driving it with someone from an earlier generation adds another dimension entirely. You're not just moving through space; you're moving through time together, hearing stories about the world as they knew it while you both experience it as it exists now.
Michael Shiwdin, Wyndham's Global VP of Integrated Marketing, framed it perfectly: the company's iconic roadside brands have been part of Route 66's story for decades. This competition brings that legacy full circle, handing travelers the keys and saying, "Go make something memorable."
The Details You Need
Full competition rules, terms, and the application portal are live on Wyndham's rewards page. The deadline and specific requirements are posted there, so don't assume anything without checking. Planning a Route 66 road trip can feel overwhelming, but winning one takes the financial pressure off and lets you focus on what matters: the drive itself and the company keeping you company.
Whether you're chasing Steinbeck's vision of escape or simply craving uninterrupted time with someone you love, Route 66 delivers both. And if you win, Wyndham's picking up the tab.
