Wyndham Is Paying $20K for a Grandparent-Grandchild Route 66 Road Trip

What Is the Wyndham Route 66 Road Trip Gig?

Wyndham is calling it The (Grand) Mother Road Trip, and the name does most of the explaining. One selected duo will spend seven nights driving Route 66 from Chicago to Santa Monica sometime between July and October 2026, staying at Hotels by Wyndham along the way and documenting the journey through photos, videos, and social content.

Here's what the full package looks like:

• $15,000 cash

• $5,000 travel stipend for flights, food, car rental, and activities

• 7 complimentary nights at Hotels by Wyndham along the route

• Wyndham Rewards Diamond membership for both travelers

• A full Route 66 itinerary covering roughly 2,400 miles of road

The stops along the way lean into classic American roadside brands like Days Inn, Super 8, and La Quinta. These are the kinds of places that have quietly been part of road trips for decades, which feels exactly right for a centennial celebration.

Why Route 66 and Why Now?

Route 66 was commissioned on November 11, 1926, which makes 2026 its centennial year. The highway runs 2,400 miles from Chicago through Missouri, Oklahoma, Texas, New Mexico, and Arizona before ending in Santa Monica, California. It was the road that connected a country during the Dust Bowl migration, the postwar road trip boom, and about a century of American restlessness.

The stops along the way have taken on a life of their own. Cadillac Ranch outside Amarillo, where ten Cadillacs are buried nose-first in a wheat field and covered in spray paint. The Blue Whale of Catoosa in Oklahoma, a turquoise roadside sculpture that's been sitting on a pond since 1972. Lou Mitchell's diner in Chicago, which has been serving breakfast near the start of the route since 1923. The Midpoint Café in Adrian, Texas, which sits exactly halfway between Chicago and Santa Monica and sells pie accordingly.

Taken together, these stops are the road as much as the highway itself. You don’t drive Route 66 just to get somewhere. You drive it to see what’s still there, and what’s changed along the way. A hundred years in, it’s still doing what it was built to do.

Who Can Apply?

The requirements are straightforward, and Wyndham is keeping the definition of family pretty open:

• Grandchild must be at least 18; driver must be 21 or older with a valid license

• Both travelers must be legal U.S. residents, including D.C., Guam, and Puerto Rico

• Step-grandparents and chosen family count if they've played that role in your life

• You'll need to be comfortable creating social content — photos, videos, reels, stories

That last point is worth taking seriously. Wyndham wants someone whose grandparent-grandchild dynamic is genuinely fun to watch. If that's you, it's your biggest competitive advantage.

How to Apply

Applications are open now and close May 1. You'll apply on behalf of both yourself and your grandparent at wyndhamrewards.com/roadtrip. Entries are judged on creativity, authenticity, and how well you capture the spirit of Route 66, which is a polite way of saying they want a duo with actual chemistry and a good story.

You can submit a short video explaining your connection and why Route 66 was made for you, or a written essay with a photo if video isn't your thing. Finalists will be asked to attend an interview, so keep that in mind when you're crafting your entry.

Some travel opportunities are worth writing home about. This one is worth applying for. Route 66 at 100 is the kind of trip that doesn’t need much selling, and getting paid $20,000 to drive it with your grandparent while the rest of the country watches is a story you’ll be telling for a long time. Just make sure you apply by May 1 before someone else beats you to it.

Frequently Asked Questions: Wyndham Route 66 Road Trip Gig

What is the Wyndham Route 66 road trip opportunity?

Wyndham Hotels & Resorts is hiring one grandparent-grandchild duo to drive Route 66 this summer as part of a paid ambassador program called The (Grand) Mother Road Trip. The selected pair will document the journey on social media and receive $20,000 total, including a $5,000 travel stipend.

How much does the Wyndham Route 66 gig pay?

The total package is $20,000, which includes $15,000 in cash and a $5,000 travel stipend for airfare, meals, car rental, and activities along the route.

When is the application deadline?

Applications close May 1, 2026. You can apply at wyndhamrewards.com/roadtrip.

Who is eligible to apply for the Wyndham Route 66 road trip?

Applicants must be at least 18 years old, and the driver must be 21 or older with a valid license. Both travelers must be legal U.S. residents, including residents of Washington D.C., Guam, and Puerto Rico. Wyndham accepts step-grandparents and chosen family.

When would the road trip take place?

The trip will happen sometime between July and October 2026, over the course of seven nights on the road.

What does Route 66 celebrate in 2026?

Route 66 was commissioned in 1926, making 2026 its 100th anniversary. The highway runs 2,400 miles from Chicago, Illinois to Santa Monica, California.

What hotels will the duo stay at?

The pair will stay at Hotels by Wyndham properties along the route, including Days Inn, Super 8, La Quinta, Ramada, and Howard Johnson. Seven nights of accommodation are included in the package.

How do I apply for the Wyndham Route 66 road trip gig?

Submit a short video or written essay with a photo explaining your connection with your grandparent and why your duo is right for the trip.