One lucky grandparent–grandchild duo will hit the open road for a once-in-a-lifetime Route 66 adventure—just in time for the highway’s 100th anniversary
PARSIPPANY, N.J., April 7, 2026 /PRNewswire/ — This summer, buckle up—because grandma’s calling shotgun. As Route 66 marks its 100th anniversary, Wyndham Hotels & Resorts and its award-winning loyalty program, Wyndham Rewards®, are bringing generations together—paying one lucky road tripper $20,000 (inclusive of a travel stipend) to hit the highway with their grandparent. Dubbed The (Grand) Mother Road Trip, the selected traveler will prove once and for all that the best travel companions might just be family.
From retro roadside motels to quirky Americana pit stops, the duo will hit the road as open-road ambassadors, diving into the heart of Route 66 while staying at familiar favorites from the Wyndham family including, Days Inn®, Super 8®, La Quinta®, Ramada®, and Howard Johnson®, brands that have been part of the American road trip for generations. Along the way, they’ll document every twist, turn, and roadside attraction for social media—the same stretch of road, documented through two very different sets of eyes.
“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.”
– Michael Shiwdin GVP, Integrated Marketing, Loyalty & Digital, Wyndham Hotels & Resorts
Buried Eldorados at Cadillac Ranch, the quirky charm of the Blue Whale of Catoosa, legendary bites at Lou Mitchell’s in Chicago, and a slice of pie at the Midpoint Café in Adrian, Wyndham’s grandparent–grandchild duo will chase down every curio, roadside oddity, and hidden gem the Mother Road has to offer. Working closely with Wyndham to craft a custom itinerary, they’ll document every mile in real time, turning each stop, every story, and all the moments in between into content that makes the rest of America wish they were in the passenger seat.
And they can be. The Route 66 centennial is an open invitation for everyone to hit the road. With hundreds of Hotels by Wyndham lining the route from Chicago to Santa Monica, every traveler has a place to pull over, recharge, and wake up ready for whatever comes next.
The Gig
Ready to hit the road? Call your grandparent—this one’s for the two of you. Take on Route 66 together, document the journey along the way, and earn $20,000 total (including a $5,000 travel stipend). You’ll spend seven nights at Hotels by Wyndham, receive Wyndham Rewards® Diamond Membership for you and your travel companion, and cover 2,400 miles of America’s most iconic highway. Here’s what you’ll take on:
Responsibilities:
- Drive Route 66 from Chicago, hitting some of the highway’s most iconic stops over one week between July and October 2026.
- Capture every mile through photos, videos, and social content for Wyndham Rewards and your own social channels.
- Stay at Wyndham hotels across multiple cities, experiencing each brand’s unique style while sharing the journey with followers at home.
Qualifications
- Applicant must be at least 18; Driver must be 21 or older with a valid license.
- Open to grandparent–grandchild pairs of all kinds, including step-grandparents and chosen family. If they’ve played that role in your life, they count here.
- A legal U.S. resident (including D.C., Guam, and Puerto Rico) with valid government-issued ID.
- Comfortable on social media and confident creating the kind of content that makes people stop scrolling—stories, reels, videos, photos, all of it.
The Perks
- $15,000 cash.
- $5,000 travel stipend to cover airfare, meals, car rental, and activities for the trip.
- Seven complimentary nights at Hotels by Wyndham along your journey.
- Wyndham Rewards® Diamond membership for you and your travel companion.
- Official Wyndham swag.
- A once-in-a-lifetime road trip with someone who’s been there for all of yours.
How to Apply
Apply on behalf of yourself and your grandparent by May 1—show us why your duo is the ultimate road trip team! Send a short video explaining your connection, sense of adventure, and why Route 66 was made for you both. Prefer to write it out? You can also submit a short essay along with a photo that captures who you are together. Applications must include:
- Full names and U.S. city/state (or territory) of residence for both grandchild and grandparent.
- Grandchild’s telephone number and email address.
- Grandchild’s publicly viewable social media profile links.
Entries will be assessed on creativity, authenticity, and the duo’s ability to capture the spirit of Route 66. In the final round of judging, both the grandchild and grandparent will be required to attend an interview. For full details, including how to apply and official rules, visit wyndhamrewards.com/roadtrip.
About Wyndham Rewards
Part of Wyndham Hotels & Resorts (NYSE: WH), the world’s largest hotel franchising company, Wyndham Rewards is the #1 hotel rewards program as named by readers of USA TODAY. Members—over 122 million enrolled around the world—earn a guaranteed 1,000 points with every qualified stay and can redeem for free nights starting at just 7,500 points. With thousands of hotels, vacation club resorts and vacation rentals globally, no other hotel rewards program is more generous. Join for free at WyndhamRewards.com.
View original content to download multimedia:https://www.prnewswire.com/news-releases/the-grand-mother-road-trip-wyndham-will-pay-you-20k-to-live-it-up-exploring-route-66-with-your-grandma-this-summer-302734958.html
SOURCE Wyndham Hotels & Resorts
