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Travel Inspiration | Road Trip
Holiday Road Trips Reimagined: 4 Classic Routes & Must-See Pitstops


Holiday travel season has finally arrived! Time to pack up the woody wagon and hit the open road. Whether you’re visiting relatives or simply making the most of winter break, a road trip is a rite of passage—and they’re about much more than getting from point A to point B.

Keeping boredom at bay on a road trip is no small feat, and that’s especially true in winter. That’s why we’ve rounded up our favorite holiday pitstops and roadside attractions along four classic U.S. road trip routes. As you finalize your holiday road trip itinerary, be sure to build in plenty of time to stop, recharge, and experience all-American holiday magic with the ones you love.

Multnomah FallsMultnomah Falls in Winter; Photo by 4nadia/

If you grew up in the 90s, you likely spent hours playing this pioneering video game. But did you know the Oregon Trail is a real place that spans the northern U.S. from coast to coast? Here’s your chance to flex those fording skills—without all the suffering and hardship, of course.

Columbia River Gorge National Scenic Area, Hood River, OR. Located just minutes outside Portland, there’s no wrong time to visit this natural wonderland. But locals know the best time is winter, when the majestic Multnomah Falls are blanketed in snow.

Field of Dreams, Dyersville, IA. Baseball may be a summer sport, but that doesn’t keep this popular tourist spot—built for the 1989 movie of the same name—from hosting a double dose of all-American magic at its annual Christmas Expo.

The Strong National Toy Hall of Fame, Rochester, NY. ‘Tis the season to introduce your kids to some of the world’s most beloved toys at this interactive museum devoted to the history and exploration of play.

Pacific Coast Highway 101Charles M. Schulz Museum and Research Center; Photo by Brennan Spark Photography, courtesy of the Schulz Museum, Santa Rosa, CA.

Offering some of the world’s most jaw-dropping coastal scenery, the northern Pacific Coast Highway stretches more than 1,000 miles from Seattle to San Francisco—and there’s no shortage of leg-stretching stops along the way.

Lewis and Clark Interpretive Center, Ilwaco, WA. If the weather outside is frightful, head inside the 158-seat theater for fascinating historical depictions or climb the glass-enclosed observation tower for some of the West Coast’s best whale spotting.

Old Town & Waterfront, Eureka, CA. Sip hot cider as you wander the charming streets of one of America’s best preserved historic districts, where more than 150 Victorian-era buildings are decked out each year in twinkling holiday lights.

Charles M. Schulz Museum and Research Center, Santa Rosa, CA. What’s a holiday party without Charlie Brown and his pal, Snoopy? This nostalgic spot pays homage to the beloved Peanuts creator with all-ages workshops and events all season long.

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Clingmans Dome Observation Tower, NCClingmans Dome observation tower, Great Smoky Mountains National Park; Photo by smartstock/

Spanning 14 states from Maine to Georgia, the Appalachian Trail is known as a hiker’s paradise. But many of its sections and trailheads are accessible by car, so you can stay toasty and warm on your holiday road trip while you dabble in the snow-blanketed scenery.

Clingmans Dome Observation Tower, NC. Just a stone’s throw from the Tennessee border, visitors enjoy panoramic views of the Great Smoky Mountains from the cozy comfort of the historic observation tower.

Harpers Ferry, WV. Known as the “psychological midpoint” of the Appalachian Trail, this historic town hosts annual events like the Olde Tyme Christmas Festival that blend holiday magic with rich Civil War history.

Bennington, VT. Looking for that quintessential New England Christmas vibe? Look no further than historic Bennington, whose quaint streets and vibrant arts culture seem custom-made for holiday cheer.

Lava River CaveLava River Cave, Flagstaff, AZ; Photo courtesy of Coleman Becker and Arizona Office of Tourism

No road trip roundup is complete without Route 66, the fabled highway stretching more than 2,200 miles from Chicago to Santa Monica. Show your kids how to get their kicks from the Great Plains to the American Southwest with these unforgettable holiday stops.

The Gathering Place, Tulsa, OK. Nestled on the Arkansas River, this 66.5-acre park boasts an array of indoor and outdoor events for all ages. Treat the family to cozy story time, crafting workshops, winter birdwatching, and more.

Sixth Street Historic District, Amarillo, TX. After checking out the graffitied graveyard at Cadillac Ranch, hit this lively downtown strip for eclectic souvenirs and some of the best tacos this side of the Rio Grande.

Lava River Cave, Flagstaff, AZ. Staying warm usually isn’t a problem in the desert, but should the temps take a dive, heat up next to this mile-long lava tube—one of only a few known volcanic wonders in the continental U.S.