How does Wyndham's initiative make family travel easier?

Wyndham’s Route 66 road trip contest is all about bringing families closer—literally. By offering $20,000 to cover expenses, they’re removing one of the biggest hurdles for travelers: cost. This isn’t just about seeing cool places; it’s about sharing those moments with someone you love, like a grandparent. Imagine swapping stories in the car, laughing over weird roadside attractions, or bonding over a plate of diner pancakes. It’s a chance to create memories that’ll last way longer than any souvenir. Plus, with more people craving experiences over stuff, this kind of trip fits right into what travelers are looking for these days—real, meaningful adventures.

What’s the real deal with Route 66’s economic boost?

Reviving Route 66 isn’t just about nostalgia—it’s a serious economic opportunity. Think about it: more travelers mean more business for local diners, motels, and shops. The U.S. Travel Association estimates this could pump up local economies by around 15% annually. That translates to more jobs, more money circulating in small towns, and even new businesses popping up to cater to tourists. It’s a win-win: travelers get an authentic slice of Americana, and communities get a much-needed boost. But it’s not just about the money—it’s about keeping the spirit of the road alive for future generations.

Are there any downsides to all this Route 66 love?

Absolutely, and it’s not all sunshine and open roads. More tourists mean more wear and tear on the route—think crowded attractions, litter, and even damage to historic sites. There’s also the risk of over-commercialization, where the road loses some of its gritty charm in favor of tourist traps. And let’s not forget the environment: more cars on the road mean more pollution, and fragile desert ecosystems could take a hit. The key is balance—enjoying the road while respecting it. That means traveling responsibly, supporting local businesses, and leaving no trace. After all, we want Route 66 to stay special for the next 100 years, too.

Is nostalgia travel here to stay, or just a passing trend?

Nostalgia travel isn’t going anywhere—at least not anytime soon. People love the idea of stepping back in time, whether it’s cruising Route 66 or visiting a retro diner. But for it to stick around, it can’t just be about looking backward. Travelers want authenticity, not just a polished version of the past. That means preserving the real stories, the local flavors, and the quirks that make places like Route 66 unique. And let’s be real: as long as there are grandparents sharing stories and travelers craving something different, nostalgia will have a place in the travel world. The trick is keeping it fresh while honoring the past.

Wyndham Will Pay You $20K to Live It Up Exploring Route 66 with Your Grandma This Summer

As Route 66 approaches its 100th anniversary in 2026, Wyndham Hotels & Resorts is offering a unique chance to experience the legendary highway in a way few ever will. One fortunate traveler and their

April 8, 2026

As Route 66 approaches its 100th anniversary in 2026, Wyndham Hotels & Resorts is offering a unique chance to experience the legendary highway in a way few ever will. One fortunate traveler and their grandparent will receive $20,000 to embark on a cross-generational road trip, a journey that promises more than just sightseeing—it’s an invitation to step into living history. This initiative reflects a broader shift in how people travel today, with more and more adventurers seeking experiences that are rich in meaning, connection, and personal growth. Route 66, often called the 'Main Street of America,' is the perfect backdrop for this kind of adventure. It’s a road that winds through the heart of the country, offering a mix of nostalgia, quirky charm, and raw beauty. Unlike typical tourist destinations that feel polished and predictable, Route 66 is alive with character—each mile tells a story, whether it’s the faded glory of a vintage motel, the friendly chatter of a roadside diner, or the vast, open landscapes that stretch endlessly under the big sky. This road trip isn’t just about reaching a destination; it’s about the people you meet, the memories you create, and the shared moments that will stay with you long after the journey ends. As the travel industry continues to evolve, initiatives like Wyndham’s highlight a growing appetite for experiences that are immersive, family-oriented, and deeply rooted in history. Whether you’re a history buff, a road trip enthusiast, or simply someone looking to reconnect with a loved one, this is an opportunity to dive headfirst into the spirit of adventure that defines Route 66.

Person standing in front of bright blue doors — Photo by Samuell Morgenstern on Unsplash

What to Expect

Embarking on a Route 66 road trip is a sensory overload in the best possible way. Picture yourself behind the wheel, the hot sun beating down on the black asphalt, shimmering in the distance. The air is thick with the scent of gasoline and frying food from roadside diners. You hear the steady hum of the engine, punctuated by the occasional blast of a truck horn and the twangy melodies drifting from the car radio, playing classic country tunes. The wind whips through your hair as you roll down the windows, feeling the grit of the desert air on your skin. You'll see vintage gas stations, quirky roadside attractions" class="internal-link">attractions like oversized dinosaurs, and sprawling desert landscapes stretching as far as the eye can see. In the evenings, the sky explodes with color as the sun sets, casting long shadows across the desolate terrain. You might even hear the lonely howl of a coyote in the distance, adding an eerie beauty to the experience. Each stop offers a taste of Americana, from the greasy burgers at classic diners to the friendly faces of the locals who have kept the spirit of Route 66 alive. It’s a journey that engages all your senses, leaving you with a deeper appreciation for the road and the stories it holds.

Wyndham Will Pay You 20K to Live It Up Exploring Route 66 with Your Grandma This Summer experience - Travel Guide

Wyndham Hotels & Resorts is making waves in the travel industry with a unique initiative aimed at celebrating Route 66's centennial. They're offering $20,000 to one lucky traveler who embarks on a cross-generational road trip with their grandparent. The year 2026 marks a time when travelers increasingly crave journeys that stir the soul—think of the crunch of gravel underfoot at a roadside stop, the laughter shared over a greasy-spoon breakfast, or the quiet awe of watching a desert sunset paint the sky in hues of orange and purple. This venture taps into that desire, blending the nostalgia of the iconic route with modern travel incentives while fostering familial bonds through shared adventures. Imagine cruising down the Mother Road, the smell of asphalt mixing with the sweet scent of blooming desert flowers carried on the warm breeze. You pass iconic landmarks like the Cadillac Ranch in Amarillo, its spray-painted cars standing as a testament to American car culture. The distant rumble of a semi-truck horn breaks the silence of the vast landscape, a constant reminder of the road's enduring legacy. The sun beats down, warming the leather seats as you cross state lines, each mile a step back in time. Consider a stop at the Blue Whale of Catoosa, a quirky roadside attraction that captures the whimsical spirit of Route 66. Don't forget to grab a classic diner meal in Tucumcari, where the neon signs still flicker, beckoning weary travelers. Embrace the unexpected detours and the stories you'll collect along the way—like the time your grandparent recounts tales of their own youthful adventures or the moment you stumble upon a hidden gem that isn’t in any guidebook.

Visitor Tips

Planning a Route 66 adventure requires some foresight. **Best Time to Visit:** Spring and fall offer the most pleasant weather, avoiding the scorching heat of summer and the potential for winter storms. **Pro Tips:** * Book accommodations in advance, especially during peak season. * Pack plenty of water and snacks, as services can be sparse in some areas. * Download offline maps and navigation apps, as cell service can be unreliable. * Bring a camera to capture the iconic sights and quirky roadside attractions. * Respect the locals and their businesses – they are the heart and soul of Route 66. **Save Money:** * Travel during the shoulder seasons (spring or fall) for lower prices on accommodations. * Pack your own meals and snacks to avoid expensive tourist traps. * Look for free attractions and activities, such as hiking trails and scenic overlooks. * Consider camping to save on lodging costs. Compare gas prices at different stations and use a gas app to find the cheapest option.

How to Get There

While Route 66 itself is a driving experience, reaching its starting point and navigating specific segments requires planning. **Metro (Chicago):** If starting in Chicago, take the 'L' train to downtown, then rent a car. A single ride on the 'L' costs $2.50. **Taxi (Chicago):** A taxi or rideshare from O'Hare International Airport (ORD) to downtown Chicago will cost approximately $40-$60. **Car:** Renting a car is essential for experiencing Route 66. Daily rental rates vary, but expect to pay around $50-$100 per day, depending on the vehicle and rental company. Consider starting your Route 66 journey in Chicago, Illinois, the traditional starting point. Alternatively, you can fly into major airports along the route, such as Oklahoma City or Albuquerque, and rent a car from there.

Frequently Asked Questions

How does Wyndham's initiative make family travel easier?: Wyndham’s Route 66 road trip contest is all about bringing families closer—literally. By offering $20,000 to cover expenses, they’re removing one of the biggest hurdles for travelers: cost. This isn’t just about seeing cool places; it’s about sharing those moments with someone you love, like a grandparent. Imagine swapping stories in the car, laughing over weird roadside attractions, or bonding over a plate of diner pancakes. It’s a chance to create memories that’ll last way longer than any souvenir. Plus, with more people craving experiences over stuff, this kind of trip fits right into what travelers are looking for these days—real, meaningful adventures.
What’s the real deal with Route 66’s economic boost?: Reviving Route 66 isn’t just about nostalgia—it’s a serious economic opportunity. Think about it: more travelers mean more business for local diners, motels, and shops. The U.S. Travel Association estimates this could pump up local economies by around 15% annually. That translates to more jobs, more money circulating in small towns, and even new businesses popping up to cater to tourists. It’s a win-win: travelers get an authentic slice of Americana, and communities get a much-needed boost. But it’s not just about the money—it’s about keeping the spirit of the road alive for future generations.
Are there any downsides to all this Route 66 love?: Absolutely, and it’s not all sunshine and open roads. More tourists mean more wear and tear on the route—think crowded attractions, litter, and even damage to historic sites. There’s also the risk of over-commercialization, where the road loses some of its gritty charm in favor of tourist traps. And let’s not forget the environment: more cars on the road mean more pollution, and fragile desert ecosystems could take a hit. The key is balance—enjoying the road while respecting it. That means traveling responsibly, supporting local businesses, and leaving no trace. After all, we want Route 66 to stay special for the next 100 years, too.
Is nostalgia travel here to stay, or just a passing trend?: Nostalgia travel isn’t going anywhere—at least not anytime soon. People love the idea of stepping back in time, whether it’s cruising Route 66 or visiting a retro diner. But for it to stick around, it can’t just be about looking backward. Travelers want authenticity, not just a polished version of the past. That means preserving the real stories, the local flavors, and the quirks that make places like Route 66 unique. And let’s be real: as long as there are grandparents sharing stories and travelers craving something different, nostalgia will have a place in the travel world. The trick is keeping it fresh while honoring the past.