Wyndham will pay you $20,000 to explore Route 66 with your grandma this summer | News

This summer, buckle up, ’cause grandma’s calling shotgun. As Route 66 celebrates 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 (including travel reimbursement) to hit the highway with his grandparent. Called The (Grand) Mother Road Trip, the selected traveler will prove once and for all that the best travel companions may be family.

From retro roadside motels to quirky Americana pit stops, the duo hit the road as ambassadors of the open road, delving into the heart of Route 66 while staying at familiar Wyndham family favorites including Days Inn®, Super 8®, La Quinta®, Ramada® and Howard Johnson®, brands that have been a part of the American road trip for generations. Along the way, they document every bend and attraction along the way for social media: the same stretch of road, documented by two very different 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 and 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 Midpoint Café in Adrian, Wyndham’s grandparent-grandchild duo hunt for every curio, roadside oddity and hidden gem that Mother Road has to offer. Working closely with Wyndham to create a custom itinerary, they document every mile in real time, turning every stop, every story, and all the moments in between into content that will make the rest of America wish they were in the passenger seat.

And they can be. Route 66’s centennial is an open invitation for everyone to hit the road. With hundreds of Hotels by Wyndham along the route from Chicago to Santa Monica, every traveler has a place to stop, recharge and wake up ready for whatever comes next.

The performance
Ready to hit the road? Call your grandparent, this one is for the two of you. Take Route 66 together, document the trip along the way, and earn a total of $20,000 (including a $5,000 travel allowance). You’ll spend seven nights at Hotels by Wyndham, receive a Wyndham Rewards® Diamond membership for you and your travel companion, and travel 2,500 miles on America’s most iconic highway. This is what you will do:

Responsibilities:

Drive Route 66 from Chicago and take in some of the highway’s most iconic stops for a 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 in multiple cities and experience each brand’s unique style while sharing the journey with followers at home.
Qualifications

Applicant must be at least 18 years old; The driver must be 21 years or older and have a valid driver’s license.
Open to all types of grandparent-grandchild couples, including step-grandparents and chosen families. If they played that role in your life, they count here.
A legal resident of the US (including DC, Guam and Puerto Rico) with a valid government-issued ID.
Comfortable on social media and confidently creating the kind of content that makes people stop scrolling: stories, reels, videos, photos, everything.
The benefits

$15,000 cash.
$5,000 travel reimbursement to cover airfare, meals, car rentals and activities for the trip.
Seven free nights at Hotels by Wyndham during your trip.
Wyndham Rewards® Diamond Membership for you and your travel companion.
Official Wyndham swag.
A once-in-a-lifetime road trip with someone who has already been there before you.
How to apply
Register before May 1 on behalf of yourself and your grandparent and show us why your duo is the ultimate road trip team! Send a short video explaining your connection, your sense of adventure, and why Route 66 was made for both of you. Would you rather write it out? You can also submit a short essay along with a photo that shows who you are together. Applications must include the following:

Full names and U.S. city/state (or territory) of residence for both grandchild and grandparent.
Phone number and email address of your grandchild.
The publicly visible links to your grandchild’s social media profiles.
Entries will be judged on creativity, authenticity and the duo’s ability to capture the spirit of Route 66. In the final round of assessment, both the grandchild and grandparent must attend an interview. For full details, including how to sign up and the official rules, visit wyndhamrewards.com/roadtrip.