Wyndham Route 66 Road Trip Contest: Win $20,000 Cash!

This summer, trade routine for the open road with The (Grand)Mother Roadtrip Contest—a heartwarming, adventure-packed opportunity that pays you to travel. Imagine cruising down the iconic Route 66 with your favorite co-pilot—your grandma or grandpa—creating unforgettable memories along the way. With a massive $20,000 cash prize, this isn’t just a getaway—it’s a paid road trip experience designed for storytelling, bonding, and pure fun.

From retro diners to quirky roadside attractions, every mile becomes part of your journey as you document your adventure and share your unique connection. This summer travel contest blends nostalgia with excitement, making it perfect for duos ready to turn their relationship into a once-in-a-lifetime experience. It’s more than a trip—it’s a family adventure giveaway that celebrates connection across generations.

What makes this even more special is the chance to showcase your story. Whether it’s laughter-filled car rides or heartfelt moments along the way, this content creator road trip opportunity invites you to capture it all. If you’ve been dreaming of a meaningful escape that combines travel, creativity, and reward, this unique travel sweepstakes delivers it all in one unforgettable package.

Spots are limited, and the deadline is approaching fast. Submit your entry and prove why your duo deserves to hit the road in style. This is your chance to turn a simple road trip into an epic, paid summer adventure.

Limit: Only one entry per person is allowed. The minimum age limit to enter the giveaway is 21. 

How to Enter in The Grand Mother Roadtrip Contest:

Entry Method #1: Video Submission via Email

During the contest period, entrants must submit an original short video via email to [email protected]. The video should feature the entrant (or entrant pair), explain their relationship, and share why they want to take the Route 66 trip together. The video can be attached (MP4 format recommended) or shared via a public link (such as cloud storage).

Entry Method #2: Essay Submission via Email

Alternatively, entrants may submit a short essay (minimum 50 words) to [email protected]. The essay should describe the relationship between the entrant pair and explain why they want to take the trip. A high-resolution photo of the entrant and accompanying participant must also be included.

Required Details              

All entries must include full names, U.S. residency, phone number, email address, and social media profiles of both participants.

Route 66 Road Trip Contest Winner Selection:

Entries are judged by a panel of three judges based on:

• Passion for Route 66 travel & adventure (33%)
• Cross-generational connection (33%)
• Overall quality of submission (33%)

Round 1 (around May 15, 2026):
Top 2 highest-scoring entries are selected as finalists and contacted for a video interview.

Round 2 (around May 28, 2026):
Finalists attend a live interview to verify their entry, share enthusiasm, and discuss social media comfort.

Final Winner (by June 2, 2026):
One winner (Entrant Pair) is selected based on interview performance.
In case of a tie, the Head Judge decides. If a finalist is unreachable or ineligible, an alternate may be chosen. 

Wyndham Mother’s Day Giveaway Prizes:

One Grand Prize winner will win:

• Seven nights of lodging at hotels within the Wyndham portfolio (ARV: $1,400 USD)
• $15,000 USD cash payment
• $5,000 USD cash payment to cover travel-related expenses, including airfare, car rental, gas, tolls, meals, and activities
• Wyndham Rewards Diamond status upgrade for one year for both members of the winning Entrant Pair
• Wyndham-branded merchandise (swag) for both individuals (total ARV: $200 USD)

(ARV: $21,600 USD)