More American road trips are turning into strings of destinations instead of a single one. Drivers link several cities in a single trip, treating each overnight stop as its own mini-vacation rather than a rest along the way to somewhere else. What used to be one long haul is starting to look like a collection of short getaways, stitched together by an open road.
The country’s 250th anniversary and Route 66’s 100th anniversary both fall in 2026, giving the American highway a reason to be part of the conversation again. Control plays a role, too. Travelers want the freedom to change plans mid-trip, skip a city that isn’t working out and add one that wasn’t on the list to begin with. It’s the kind of trip where the plan can change on day two without throwing off the whole vacation.
Hilton’s own survey found that 71% of Americans plan to drive on their next vacation this year. Almost as many, 61%, say they won’t drive more than five hours without stopping at a hotel, a sign many road trippers already build multiple stops into their plans.
Hotels market to travelers making multiple stops
Hampton by Hilton properties sit close enough together that road trippers are rarely more than 30 minutes from the next one on most major highways. That density matches what road-tripping guests say they care about most. A comfortable bed is the top priority for 90% after a full day of driving, and 83% won’t get back on the road without free breakfast first.
Campgrounds and planning apps catch up
Nearly 30 KOA campgrounds sit within an hour of Route 66 as the historic highway heads toward its 100th year, part of a network that spans more than 500 locations across North America. In a survey of its own campers, KOA found 43% are planning a heritage or history-focused road trip this year, with a stated interest in longer routes that string together small towns and roadside landmarks rather than one final stop.
Roadtrippers, a trip-planning app with no ties to any hotel brand, has now been used to plan more than 42 million trips covering 35 billion miles. This year, the company partnered with America250, the organization behind the country’s anniversary celebrations, on a campaign focused on experiencing the country from the road.
Route 66 stretches across 8 states
Route 66 runs roughly 2,400 miles through eight states, from Illinois to California, and turns 100 this year. A survey found 41% of U.S. adults plan to drive some part of it this year, with another 15% saying the centennial made them interested for the first time. Few travelers drive the highway start to finish in one trip. Its length across eight states makes multiple overnight stops the practical way to cover it.
Luxury travel tells the same story
Classic Vacations, a luxury travel advisor network, named “hotel hopping” one of its defined trends for summer 2026, describing multi-destination itineraries that pair city time with a stretch in the countryside or coast. A five-star travel network and a mainstream highway hotel chain describing the same basic behavior suggest the pattern extends across price points, not just to travelers looking to save money. Several travel companies, not just one corner of the market, are now seeing customers plan trips the same new way.
This year’s anniversary gave the trend its moment, but it won’t need an anniversary to keep going. Hotel chains, campground networks and planning apps are already catering to guests who stop more than once, and that positioning doesn’t disappear when 2026 ends. The next version of the American road trip may not be about the mileage at all. It may be about how many places a traveler can fit into one route.
Mandy Applegate 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.