Road trips used to mean point A to point B, with a few gas station stops in between. Not anymore. Drivers are stringing together entire cities now, treating each overnight stop like its own vacation instead of a pit stop on the way to somewhere else.
Part of it is timing. The country turns 250 this year, and Route 66 hits its 100th birthday too, so the open road has a reason to be in the conversation again. But a lot of it comes down to control. Travelers want to change plans on day two if a city isn’t working out, or add a stop that wasn’t even on the map to start.
Hotels Are Already Planning Around It
Hilton’s own survey found that 71% of Americans plan to drive on their next vacation this year. Almost as many, 61%, said they won’t drive more than five hours without stopping at a hotel, which tells you people are already building multiple stops into the trip.
Hampton by Hilton properties are rarely more than 30 minutes from the next one on major highways, and that matters to road trippers. A comfortable bed is the top priority for 90% of guests after a full day of driving, and 83% won’t get back in the car without free breakfast first.
Campgrounds and Apps Are Catching Up Too
Nearly 30 KOA campgrounds sit within an hour of Route 66 as the highway heads into its 100th year. In KOA’s own survey, 43% of campers said they’re planning a heritage- or history-focused road trip this year, with a growing appetite for longer routes that string together small towns instead of driving straight to one final stop.
Roadtrippers, a trip planning app, has now helped plan more than 42 million trips covering 35 billion miles. This year the company partnered with America250 on a campaign built around experiencing the country from the road.
The excitement isn’t limited to app users. A separate survey found 41% of U.S. adults say they plan to drive some part of Route 66 this year, with another 15% saying the centennial made them interested for the first time. Tulsa is leaning into its own piece of that celebration with a summer-long party planned around the highway’s birthday.
Even Luxury Travelers Are Doing It
Classic Vacations, a luxury travel advisor network, named hotel hopping one of its trends for summer 2026, describing trips that pair city time with a stretch in the countryside or on the coast. When a five-star travel network and a mainstream highway hotel chain are describing the same behavior, it’s safe to say this isn’t just about saving money.
The anniversary gave this trend its moment, but it’s not going away when the celebrations end. Hotels, campgrounds and planning apps are already built around guests who stop more than once, so if you’re mapping out a summer trip, consider skipping the straight shot and building in a few extra stops along the way.
Mandy is a luxury travel, fine dining and bucket-list-adventure journalist with expert insight from 47 countries. She uncovers unforgettable experiences around the world and brings them to life through immersive storytelling that blends indulgence, culture and discovery, and shares them with a global audience as co-founder of Food Drink Life. Her articles appear on MSN and through the Associated Press wire in major U.S. outlets, including NBC, the Daily News, Boston Herald, the Chicago Sun-Times and many more.