There are over 4 million miles of roadway in the U.S. — and though many routes are just a way to get from point A to point B, some are remarkable enough to be destinations in and of themselves.

The most interesting roads in America

Here are 11 standout stretches of road to tempt your inner wayfarer.

1. Mount Evans Scenic Byway, Idaho Springs, Colorado

Folks in Colorado love to scale “fourteeners” (as the 58 mountains in the state that top 14,000 feet are called). If you’d rather skip the climb, you can cruise up Mount Evans’ highway instead. Reaching 14,130 feet in elevation, it claims to be North America’s highest paved road. I can personally attest that the view from the top is literally breathtaking.

2. Canton Avenue, Pittsburgh, Pennsylvania

We have some pretty steep streets here in San Francisco, California, but none can compare with Pittsburgh’s Canton Avenue. This cobblestoned street has a brake-defying maximum gradient of 37 degrees. It’s officially the steepest public street in the country (and probably the world, though Baldwin Street in Dunedin, New Zealand, has also claimed that title).

3. Tail of the Dragon at Deal’s Gap, Robbinsville, North Carolina

The U.S. has no shortage of mountain ranges, which means lots of twisting roads filled with hairpin curves. But the windiest road of all may be this 11-mile stretch of Route 129, which boasts no less than 300 turns. Motorcycle and sports car enthusiasts love this route, which can get pretty crowded in the summer months.

4. Lower Wacker Drive, Chicago, Illinois

Movie buffs may recognize this underground shortcut from The Blues Brothers, The Dark Knight, and Batman Begins. A white-knuckle ride of a road with sudden twists and turns, blind merges, and a long tunnel of pillars, it seems tailor-made for a Hollywood car chase. Portions of Lower Wacker were recently reconstructed. It’s not quite as hair-raising as before, but it’ll still boost your adrenaline.

5. Overseas Highway, Florida Keys

Skimming over the turquoise waters of the Atlantic Ocean and the Gulf of Mexico, this 128-mile highway consists of 42 bridges stretching from one tropical island to another. The southernmost portion of Highway 1, it joins mainland Florida with Key West, following the approximate path of an old railway that was wrecked by a hurricane in 1935.

6. White Rim Road, Canyonlands National Park, Moab, Utah

If you want to get off the pavement and live on the edge for a while, take a spin on this unimproved, 100-mile road. Not to be attempted without a 4×4, the trail circles the Island in the Sky mesa (mostly right along the sheer cliffs), offering fantastic views of the national park’s canyons and arches.

7. Drive-Through Trees, Highway 101, California

In the early years of national parks, tunnel trees were fairly common, created as a way to generate interest in the parks. Though that custom ended as conservation practices changed, there are 3 drive-through redwoods still remaining in Northern California, all located along Highway 101 on the Redwood Coast — the Chandelier Tree in Leggett, the Shrine Drive-Thru Tree in Myers Flat, and the Tour Thru Tree in Klamath.

8. Volcano Road, Capulin Volcano National Monument, New Mexico

Feel like driving up the side of a volcano? Here’s your chance. (Don’t worry, it’s extinct.) This 2-mile road spirals around the cinder cone’s circumference up to its rim, where you can safely walk into the crater itself — a rare opportunity.

9. Dinosaur Diamond Prehistoric Highway, Colorado and Utah

Dinosaur fans and geology buffs alike will appreciate this highway, which passes through some of the richest fossil deposits in the world. Check out a plethora of dinosaur museums, see rock art at dozens of archaeological sites, explore quarries where bones are still encased in rock, or even take part in a one-day dinosaur dig.

10. Great River Road, Northern Minnesota to Southern Louisiana

This 3,000-mile byway aligns with the Mississippi River, America’s most iconic waterway. The route cruises by charming towns and big cities like St. Louis, Missouri; Memphis, Tennessee; and New Orleans, Louisiana, whose histories are inseparable from “Ol’ Man River.” And you can learn more about the river’s heritage at over 70 interpretive centers along the way.

11. Journey Through Hallowed Ground National Scenic Byway, Maryland, Pennsylvania, Virginia, and West Virginia

Stretching 180 miles from Gettysburg, Pennsylvania, to Monticello, Virginia, this region is richer in national history than anywhere else in the country. Visitors can tour hundreds of Civil War battlefields, notable sites like Harpers Ferry National Historic Park and General Robert E. Lee’s headquarters, and the homes of 9 U.S. presidents (including Thomas Jefferson, James Madison, Theodore Roosevelt, and Dwight D. Eisenhower).

If you’re into roads, check out some of the creepiest roads in the world, plus what might be in store in the future. Before you head out on your next road trip, make sure you have the right auto insurance.

Travel hacks | Destinations


about Ellen

Ellen has spent many years as a professional wordsmith, helping to shed light on such topics as world travel, cargo pants, and the porosity of bath tiles. As a freelance copywriter for Esurance, she brings her boundless curiosity to the world of insurance. Outside work, she can be found cheering on the San Francisco Giants, hiking in the Oakland hills, and (barely) resisting smuggling penguins home from Antarctica.