Happy birthday to America’s most iconic road trip, Route 66, which turns 100 this month. Stretching from Chicago to LA, it winds through neon-lit towns and landscapes that tell the story of the country itself.

You’ll pass through places like Amarillo, where Dust Bowl history still lingers, and Tulsa, where legends like Elvis and Johnny Cash once played stages that are still alive today.

But the real magic happens between the stops, in the offbeat, kitschy roadside attractions you’ll be talking about long after the trip ends.

These are the places worth pulling over for.

PLAN YOUR ROUTE 66 STOPS→

Here’s your chance to catch up on our most popular stories in March:

You might have missed this in yesterday’s email while out on an egg hunt, but it’s worth calling out again. If flying already feels expensive, it’s about to get worse, especially if you wait until the last minute.

SEE NEW FEES→

Rome isn’t a one-day city, but sometimes that’s all you’ve got.

If you’re arriving via cruise, you’ll dock in Civitavecchia, about 43 miles away, with only a few hours to explore. The good news: with the right plan, you can still hit the highlights in five hours or less.

PLAN YOUR ROMAN HOLIDAY→

From California poppy super blooms to Texas bluebonnets and wisteria-draped streets in Charleston, spring brings a full spectrum of color across the US. Here’s when and where to go to catch peak blooms.

FIND THE BEST BLOOMS→

Philadelphia is set to host six World Cup matches in 2026, and the city is already gearing up.

With a stadium just minutes from downtown, you can spend the morning at the Liberty Bell and be in your seat by kickoff. But with tens of thousands of fans arriving, hotels won’t stay available for long.

START PLANNING YOUR PHILLY TRIP→

The Matador Editorial Team