Wyndham Hotels & Resorts will reward one lucky grandparent–grandchild duo with $20,000 to embark on a once-in-a-lifetime Route 66 road trip during the highway's 100th anniversary this summer.
How It Works
Wyndham Rewards will task the two contest-winning family members with driving Route 66 from Chicago, touring some of the highway's most iconic stops on the way to the Pacific Ocean over one week between July and October 2026.
They'll capture and share their experience through photos, videos and social content for Wyndham Rewards and their own social channels, and also stay at Wyndham hotels across multiple cities.
Perks include $15,000 cash and a $5,000 travel stipend to cover airfare, meals, car rental and activities for the trip, in addition to seven free nights at Hotels by Wyndham, Wyndham Rewards Diamond membership for the winner and their travel companion and official Wyndham swag.
How To Apply
Travelers age 18 and up (21 with a valid license to be the driver) can apply on behalf of themselves and their grandparent by May 1.
Williams, Arizona along Route 66. (Photo Credit: Hanna Tor/Adobe)
Applicants must submit full names and U.S. city/state (or territory) of residence for both grandchild and grandparent, along with the grandchild’s telephone number and email address and the grandchild’s publicly viewable social media profile links.
Send a short video explaining your connection, sense of adventure and why Route 66 was made for you or submit a short essay along with a photo that captures who you are together, says Wyndham, which will assess entries on creativity, authenticity and the duo’s ability to capture the spirit of Route 66.
Keep in mind that both the grandchild and grandparent will be required to attend an interview for the final round of judging.
"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," said Michael Shiwdin GVP, Integrated Marketing, Loyalty & Digital, Wyndham Hotels & Resorts.
"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."
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