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Win Wyndham Hotels & Resorts’ Route 66 Sweepstakes

by Aoife O'Riordan

Apr 15, 2026

© North2south | Dreamstime.com

Destinations / North America

Wyndham Hotels & Resorts just launched The (Grand) Mother Road Trip Sweepstakes in honor of Route 66’s 100th anniversary. The hotel brand and its loyalty program Wyndham Rewards are bringing generations together by giving one lucky road tripper $20,000 (inclusive of a stipend) to hit the highway with their grandparent.

 

From quirky American pit stops to retro roadside motels, one winner and their grandparent will serve as Wyndham’s open-road ambassadors, driving into the heart of Route 66 while staying at familiar favorites from the Wyndham family.

 

Along the way, the winning duo will document every turn, twist and roadside attraction for social media, capturing the same stretch of road but through two different perspectives. This includes visits to Cadillac Ranch, Lou Mitchell’s in Chicago, the Blue Whale of Catoosa, Midpoint Café in Adrian and more.

 

The winner and their grandparent will work closely with Wyndham to craft a custom itinerary.

 

How can you enter? Send a short video explaining your connection, sense of adventure and why Route 66 was made for you and your grandparent. Or you can submit a short essay along with a photo that captures who you are together. Apply here.

 

Applicant must be at least 18 and driver must be 21 or older with a valid license. Applications are open to grandparent-grandchildren pairs of all kinds, including step-grandparents and chosen family. In other words, if they’ve played an important role in your life, they count here.

 

Perks include $15,000 cash; a $5,000 travel stipend to cover airfare, meals, car rental and activities; seven complimentary nights at Hotels by Wyndham along the journey; Wyndham Rewards Diamond membership for you and your travel companion; and official Wyndham swag.

 

Applications close May 1.

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