Built in 1869, this now-retired structure looks more like a medieval fortress than a county lock-up.

This diner serves Route 66 nostalgia and what it claims is the 'original' hot dog on a stick.

This abandoned 19th century orphanage started as a boarding school for children of Civil War veterans.

This tiny historic jail along Route 66 is the perfect fit for exactly one criminal and their partner-in-crime.

A journey begins with a single step, and for many, the road-trip of a lifetime started at this Chicago intersection.

At the largest railway museum in the United States, you can see everything from an early steam engine to a functioning Thomas the Tank Engine.

This tribute to a local man towers within a quaint lakeside park.

This national park on the shore of Lake Michigan features remarkable dunes that lie at the heart of a Chippewa legend.

An enormous roadside pan tells the story of a battle for pie glory.

National Mall monument to the inventor of the screw propeller.

The collection is housed in an exquisite mansion that makes you feel like you've been transported to an Italian villa.

A clear blue swimming hole with hidden caves, still unexplored.

A classic Route 66 landmark that was built with scrap lumber and is held together with kitsch and puns.

A collection of anti-communist sculptures stands watch in the Mojave Desert.

Like a kitschy mirage in the Mojave, this eatery serves up classic 50s-style diner meals and a dinosaur sculpture garden.

A desert ghost town—occupied for only 12 years—was once home to more than 500 silver mines.

The ghost town that ended up on Ebay.

A pair of large white marble lions guard this stretch of the Mojave Desert, and it is utterly mysterious how they got there.

The "world's biggest dinosaur" once housed a creationist museum in its abdomen.

Hundreds of trees made from glass bottles make up this forest on Route 66.

High on a hill overlooking Los Angeles lives a world famous, high-power conical Tesla Coil.

These delicate buggers are some of the rarest fossils that have bubbled up from the Tar Pits.

A second generation sun-powered marvel lights up the night.

An eerie natural formation that looks right back at you.