Everyone has a different travel “bucket list.” Mine includes Japan, Africa, Iceland, and Hawaii, while other people may dream of visiting Norway, New Zealand, or France.
Many U.S. travelers are drawn to certain destinations each year because of events such as the Olympic Games or special concerts. One massive event dominating the 2026 travel landscape is the FIFA World Cup.
Another is the Route 66 Centennial, according to Future Partners 2026 report.
“At 47.6 percent overall interest, Route 66 is one of the highest-performing travel occasions in this year’s survey — and its standout characteristic is income-agnostic appeal: interest is consistent across all income bands, from 47.7% among those earning under $50K to 50.5% among the $100K–$199K segment,” reveals the report.
While Route 66 is a popular tour on its own, being one of the first highways in the U.S. Federal Highway System passing directly through the heart of eight states, this year the route celebrates 100 years since its inception, making it even more attractive.
To celebrate its Centennial in 2026, Wyndham Hotels will pay one lucky traveler $20,000 to take the trip with their grandmother.
Wyndham Hotels will pay $20k to explore Route 66 with grandma
Wyndham Hotels shared on April 7 that it will pay one lucky road tripper $20,000 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,” the hotel giant said in the press release.
“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,” stated Michael Shiwdin, Wyndham GVP for integrated marketing, loyalty & digital.
Related: Marriott makes huge changes to its loyalty program
The highway’s appeal isn’t just historical; it’s deeply personal for those who’ve experienced it firsthand.
“Driving it from beginning to end opened my eyes to corners of America many never experience. Set against a kaleidoscope of landscapes — from deserts to mountains to cities to endless plains — it reveals stories of resilience, ingenuity and pride, kept alive by generations of travelers and small-town stewards,” a traveler Erica Bray wrote for The Extra Mile Magazine.
The (Grand) Mother Road Trip deal highlights:
- The prize: You get $15,000 in cash plus a $5,000 travel budget for gas, food, and fun.
- The trip:A 7-day drive from Chicago to California along the famous Route 66 to celebrate the highway’s 100th birthday.
- Free stays:7 free stays at Wyndham hotels (like Days Inn and Super 8).
- VIP Status: Both you and your grandparent get Wyndham Rewards Diamond Membership, which usually offers perks such as room upgrades and late checkout.
More than a tourist, the lucky traveler should be an open-road ambassador
The lucky traveler who wins the prize has certain responsibilities, Wyndham noted. The idea is to be more than just a simple tourist and serve as an open-road ambassador.
Travelers’ responsibilities on the road
- Two perspectives: Wyndham wants to see the road through two sets of eyes: younger and older.
- Content creation: The traveler must be comfortable making social content for Wyndham Rewards and their own social channels. This includes filming videos and taking high-quality photos.
- Timing: The trip must take place over one week between July and October 2026, hitting some of the highway’s most iconic stops.
Specific Route 66 stops
The trip covers 2,400 miles from Chicago to Santa Monica. Wyndham suggests visiting these specific famous landmarks:
- Lou Mitchell’s (Chicago): A legendary diner for breakfast.
- Blue Whale of Catoosa (Oklahoma): A famous giant waterfront structure.
- Cadillac Ranch (Texas): Where cars are buried nose-first in the ground.
- Midpoint Café (Texas): Famous for being the exact halfway point of the route and serving great pie.
Wyndham Hotels will pay $20k to a lucky traveler to explore Route 66 with their grandma.
Nyokki/Shutterstock.com
Who qualifies for the (Grand) Mother Road Trip and how to apply
Applicants must be legal U.S. residents (including D.C., Guam, and Puerto Rico) with a valid government-issued ID. They also need to be at least 18, while drivers must be 21 or older with a valid license.
Wyndham accepts biological, step-grandparents, and chosen family, saying, “If they’ve played that role in your life, they count here.”
How to apply
To enter, travelers interested in the special Route 66 road trip must submit their application by May 1, providing the following.
- A video or essay: A short video is preferred, but you can write an essay with a photo. You must explain your connection to your grandparent and why Route 66 was made for you both. Include full names and U.S. city/state (or territory) of residence for both grandchild and grandparent, as well as the grandchild’s telephone number and email address.
- Social media links: You must provide links to your public social media profiles so they can see your content-making skills.
- The interview: If you are chosen as a finalist, both you and your grandparent must participate in an interview with the judges.
Wyndham Hotels Route 66 campaign reflects 2026 travel trends
The U.S. travel industry currently faces an interesting contradiction. Even as consumers are generally squeezing their wallets and increasingly seeking deals, actual travel spending has reached all-time highs.
“…The average maximum annual leisure travel budget climbed to a new record high of $6,630 — surpassing last month’s record and running nearly $1,000 above this time last year,” according to the Future Partners State of the American Traveler report.
Wyndham Hotel’s The (Grand) Mother Road Trip campaign comes at a perfect time for another key reason. The Forbes 2026 Travel Trends report highlights nostalgia as one of the biggest drivers of 2026 travel.
“Travelers are increasingly booking vacations in search of a feeling, rather than by destination. From nostalgia-driven escapes to human-centered rituals, early signs suggest that travel trends in 2026 center around journeys that feel authentic and connected,” wrote Forbes’ Alex Ledsom.
Likewise, industry reports suggest that travelers are shifting away from bucket-list trips to simpler, more flexible travel “that leave[s] them feeling recharged, not depleted,” according to RVshare’s report.
A AAA Texas survey from October 2025 even revealed strong interest in Route 66 travel during the 2026 Centennial, noting that “41% of U.S. adults plan to visit some part of Route 66 in 2026, with another 15% expressing interest after learning about the upcoming Centennial.”