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Note: All travel is subject to frequently changing governmental restrictions—please check federal, state and local advisories before scheduling trips.

With gas prices low and the current aversion to air travel in full swing, now is the time to scratch that travel itch and hit the open road. The common wisdom is that summer was made for road trips, but we beg to differ. Every season is road trip season in our opinion. Read on to discover the best season to tackle America’s most iconic road trips. Your adventure begins here!

RELATED: Road tripping California’s Hwy 395


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Putting key to ignition and hitting the open road in search of adventure and new horizons is the ultimate American journey. Everyone knows to traverse New England in autumn, but what about everywhere else? Here are 10 iconic U.S. road trips and the best times of year to take them.


Blue Ridge Parkway
This curvy drive fires up the imagination with the promise of dramatic mountain scenery, picturesque small towns and spine-tingling, zigzag curves along its 469-mile scenic trek. The journey kicks off in crunchy, cool Asheville and ends in Shenandoah National Park in Virginia and is best traveled in spring when wildflowers are in peak bloom.

The Loneliest Road in America
Transcontinental U.S. 50 includes a Nevada portion so desolate it has been named the Loneliest Road in America. But we mean it to include a grand road trip that loops all around the Silver State and includes weird attractions like the Amargosa Opera House, forgotten Pioche, Valley of Fire State Park, Las Vegas and Reno and so more. Go in spring to beat the heat. 


Great River Road
Follow the Mighty Mississippi in all her glory along this rambling 2,000-mile trek which touches no less than 10 states as it hurdles from Minnesota toward New Orleans and touches bluff-top views in Wisconsin, a touch of bluegrass in Kentucky and charming riverside towns in Arkansas and Mississippi along the way. Cool off in steamy N’Awlins with a hurricane at the finish line.

Lake Michigan Circle Tour
This 900-mile excursion circumnavigates a beautiful Great Lake while taking in the dramatic scenery of four states including picturesque small towns, lighthouses, sandy beaches and gorgeous lakefront sunsets and sunrises. Start and end in thrilling Chicago but escape city life in woodsy Wisconsin and Michigan. For heat without humidity go in either June or September.


Pacific Coast Highway
The grand icon of coastal highways, this California road trip is best started in sunny Malibu and finished in buzzy San Francisco. Laidback cities like Santa Barbara and Santa Cruz and earthy big Sur are stunning, but the real thrill is the coastline’s crashing waves, spiky trees and spine-tingling hairpin turns your vehicle makes along the way. Fall is quiet and virtually fog free.

Route 66
The most famous road trip on earth boasts Chicago and L.A. as its start and finish line, but this two lane, 2,000-mile trip is mostly a trek through small town America full of kitschy highlights like the Blue Whale of Catoosa, the Wigwam Motel, Cadillac Ranch and so much more. The scenery is constantly shifting and is universally stunning in September and October.


 The Overseas Highway
Bid adieu to Miami and put a few clicks on the old odometer in pursuit of the Florida Keys, a sun-drenched drive surrounded by turquoise water. The adventure includes John Pennekamp State Park in Key Largo, the dramatic 7-Mile Bridge, the tranquil Lower Keys and the main prize, the quirky Conch Republic—a.k.a. Key West! A winter drive is perfectlylovely.

The Road to Hana
Rent a Mustang convertible and hit up Hawaii’s most scenic roadway as it loops around numerous waterfalls, black sand beaches, spindly palm trees, roadside farm stands peddling fruit smoothies and impossibly delicious banana bread and scenic vistas galore. From start to finish it’s a mere 64.4 miles, but you’ll stop so often this journey will take a full day indeed!

Tagged: California, Hawaii, Las Vegas, Midwest

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Jason Heidemann

Jason Heidemann

Jason is a Lead Content Specialist for Expedia Group, and manages content initiatives across numerous Expedia-owned brands. His work has been featured in the Chicago Tribune, Time Out, the Huffington Post, Chicago Magazine, Passport and many others.

One thought on “The perfect road trip for every season (infographic)”

  1. How do I get further details on the Lake Michigan Circle tour. Recommendations on what to see, where to stay, etc.

    Thanks, Margie

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