Wyndham Offers $20K Route 66 Road Trip With Grandparent
Wyndham Hotels & Resorts is launching a unique travel campaign that will award one grandparent–grandchild duo $20,000 to experience an iconic American road trip along Route 66. The initiative celebrates the highway’s 100th anniversary and taps into the growing demand for multigenerational travel experiences.
Through its Wyndham Rewards program, the company will select one winning pair to embark on a week-long journey from Chicago to the Pacific Coast between July and October 2026. The trip will include stops at some of Route 66’s most recognizable landmarks, offering a mix of nostalgia, exploration, and storytelling opportunities.
The selected duo will be required to document their journey through photos, videos, and social media content, sharing their experiences across both Wyndham’s platforms and their own channels. The campaign is designed to highlight the cultural significance of Route 66 while promoting Wyndham’s portfolio of roadside and destination hotels.
The prize package includes $15,000 in cash and a $5,000 travel stipend to cover airfare, meals, car rental, and activities. In addition, winners will receive seven complimentary nights at participating Wyndham properties, Wyndham Rewards Diamond status for both travelers, and branded merchandise tied to the campaign.
Applications are open to travelers aged 18 and older, with a minimum age of 21 required for the designated driver. Interested participants must apply by May 1, submitting details for both the grandchild and grandparent, including their names, location, and contact information. Applicants must also provide links to publicly accessible social media profiles.
To complete the application, candidates are required to submit either a short video or a written essay accompanied by a photo. Submissions should highlight their relationship, sense of adventure, and why they are the ideal pair to represent the spirit of Route 66. Entries will be evaluated based on creativity, authenticity, and storytelling ability.
Shortlisted finalists will be invited to participate in an interview as part of the final selection process. Wyndham said the campaign aims to celebrate the enduring appeal of road travel while encouraging families to create shared experiences across generations.
The promotion underscores a broader trend in the travel industry toward experiential and multigenerational journeys, positioning Route 66 as a timeless symbol of exploration and connection.
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