A Road-Tripper's Guide To Some Of The Country's Oddest, Most Amazing Roads

A Road-Tripper’s Guide To Some Of The Country’s Oddest, Most Amazing Roads

Growing up, my family went on a lot of car trips. A lot of them. Along with our trusty steed, the maroon minivan, my mom, sister and I journeyed all around the country, from Death Valley to Cape Cod, Yellowstone to Galveston, and as many points as we could hit in between. My interest in geography came, in large part, from my role as a navigator on these trips. Examining road maps and AAA guides, I came to appreciate a good highway. Here are seven roads that I believe are worth building a dream road trip around; some of them I’ve already visited, some are definitely in my future. I don’t know about you, but my favorite kind of road trip includes an excursion off the beaten track for excitement, danger and mayyyybe a covered bridge or two. If I’m lucky.

Like You Need Another Reason Not To Pick Up Hitchhikers: Archer Avenue, Illinois

The Chicago area’s most famous ghost story involves not a mansion or an abandoned asylym but a single stretch of roadway. Dozens of young men have reported picking up an attractive blonde on Archer Ave in Justice, Illinois, and dropping her off at Resurrection Cemetery, where she vanishes once past the gates. I’d be tempted to call it the work of an audacious girl with an amazing sense of humor, but reports of incidents go back as far as 1930s. The name of the ghost is Resurrection Mary, and the story goes that she got into a fight with her boyfriend late one night and stormed out of the dance hall. She was shortly thereafter hit by a car while walking along the road in the dark and died; now she hitches rides to her final resting place just a few miles down the road. Research efforts by local author Ursula Bielski have recently tied the legend to an actual girl, Anna Marija, who was struck by a car on the road in 1927. Spooky.

These Curves Are All Natural: Going-To-The-Sun Road, Montana

You may recognize these two lanes of twisting, scary-cliff-adjacent roadway from the opening of The Shining. That opening captures two aspects of the road that make it so noteworthy: the beauty of its scenery and its impressive lack of guardrails. Named, logically enough, for nearby Going-to-the-Sun Mountain, the roadway can be found on both the National Parks Service’s list of National Historic Landmarks and the American Society of Civil Engineers’ list of National Civil Engineering Landmarks — a dual distinction usually reserved for bridges and lighthouses. Traversing across 50 miles of Glacier National Park’s interior, the road is a case study in daring design and construction, featuring swooping curves, nail-bitingly-scarce shoulders and treacherous elevation climbs and dips, carved into mountainsides. Completed in 1932, it took 11 summers and a budget of just over $2 million to construct. Trip-planning note: save this one for a mid to late summer roadtrip. In June of this year, the road still had drifts 20 feet deep; with so much snow to contend with, plows can sometimes cover only a few hundred feet per day. (During the spring snows, you can track the plows’ progress at the park’s website.)

Hitch Up Your Buggy: Covered Bridge Scenic Byway, Ohio

Do you like covered bridges? Do you really like covered bridges? How do you feel about barns? You are way into neat old barns? Hooo boy, do I have the road for you! Forty-four miles of the best darn covered bridges, rustic barns and charmingly ramshackle fences this side of that calendar in your grandmother’s kitchen. It’s like living stock photography. Following State Route 26, between Marietta and Woodsfield, Ohio, you will drive across eight historic covered bridges, between which you’ll pass a series of barns painted with quilts and Depression-era tobacco pouch ads. Though I’m sure it’s gorgeous year-round, it seems like an ideal trip for autumn leaves viewing. Also, there is a not-too-small chance you will have to stop for livestock in the road.

Best Place To Befriend A Buffalo: I-90, South Dakota

Yes, I’m serious, the section of I-90 that passes through South Dakota is one of America’s greatest roads. A more or less straight line east-west, this particular section of Interstate 90 ranges across expansive farmland, Sioux reservations, the Badlands and Black Hills. Along the way you’ll cross the Missouri River, pass the Buffalo Gap Grasslands (where there are actual buffalo just, like, hanging out), Mount Rushmore and Crazy Horse monuments and come within spitting distance of the exactly-what-you-think-it-is Corn Palace. Most importantly, you will be treated to a truly staggering number of signs directing you to the town of Wall, home of the legendary Wall Drug, the world’s largest drugstore. Make sure you get your free ice water! Also, and I’m speaking from personal knowledge here, there are spots along I-90 where you can totally pull over, get out of your car and feed prairie dogs, buying your “prairie dog food” from one of the manned stands along the highway. Some parts of the landscape are so filled with holes they’re downright whack-a-mole-esque (though way cuter and featuring minimal whacking). I don’t know if they’re legally sanctioned, but I do know that they’re a lot of fun.

You Say “Steve,” I Say “McQueen”: Lombard Street and others, San Francisco

It’s not enough that it has a series of eight hairpin turns on one city block. It’s not enough that it’s paved with relatively uneven bricks. It’s not enough that it has a mandatory (and heavily enforced) five-mph speed limit. No, the famous block of Lombard Street is magnificently steep as well. Drivers navigate an astounding 27-percent gradient from the top of the one-way block to the bottom of Russian Hill. Though it’s the most famous, Lombard isn’t even the steepest street in San Francisco: both 22nd St and nearby Filbert Street claim a 31-percent gradient. And they’re just a straight shot down. Vermont Street, a mere four miles away, has only seven turns, but the turns are much sharper. The neighborhood hosts an annual Bring Your Own Big Wheel event, where hundreds of people race down the hill on, as the name suggests, plastic tricycles. Afterwards, unwanted trikes are donated to the San Francisco Fire Dept’s charity. (And should you want to follow in the tracks of that car-chase scene in Bullitt, an enterprising fan has a map for you here.)

Watch Out For Road Rash: Tail of the Dragon, North Carolina

Tail of the Dragon, located in Deal’s Gap (population: six), is an 11-mile section of US Route 129. Though the scenic overlooks of Calderwood Lake and views of the southern edge of the Great Smoky Mountains are well worth mentioning, it’s this road’s 318 bends that give it a place on our list. The reckless driver in you might be tempted to zip through it — the all-time record is a celeritous eleven minutes — but feel free to chicken out once you take in the Tree of Shame, a large tree adorned with broken motorcycle parts from crashes, a “makeshift shrine dedicated to those bitten by the dragon.” As the sign says, “All Pain & No Gain.” (Indeed, this grisly map marks the locations of the 31 deaths that have occurred on the highway since 2000.) Weaving by such landmarks as Gravity’s Cavity, Crud Corner and Beginner’s End, the serpentine highway is an ideal destination for daredevils, sports car drivers and anyone with really excellent brakes. But be careful of your fellow vehicles on the road: there is a petition out to ban 18-wheeler trucks as the sharp turns mean big rigs occasionally cross into the opposite lane.

Get Your Shining Seas: Overseas Highway, Florida Keys

And finally, the mother of all scenic journeys, the 127 miles of road that link the Florida Keys. Long stretches of this highway were originally a railway, but, after a 1935 hurricane damaged the original tracks beyond repair, the rail company sold what remained of the roadbed and bridges to the state of Florida. This highway is gorgeous, surrounding you on both sides with shimmering sea. Make the hours last longer: along the way, visit the self-proclaimed capital of diving, Key Largo, for lessons and explore some area reefs. Grab lunch at one of the numerous tiny Cuban restaurants in the area. Go to Bahia Honda State Park to gaze at an incredibly well-preserved rail-truss bridge, or stop by Duck Key to pat a dolphin: they’re rubbery! The drive ends in Key West, at which point, since this is the only road into or out of the Keys, you get to do the whole thing over again!

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Victoria Johnson is a cartographer and this is her Tumblr.

Photo of Resurrection Cemetery by MrHarman; Hills Bridge photo courtesy of US Forest Service; Wall Drug sign courtesy of Wikipedia; Lombard Street photo by Y6y6y6; Tree of Shame photo by RinzeWind; Overseas Highway photo by Marc Averette.