Highway to Heaven: 15 Iconic U.S. Road Trips

atacama desert
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Does the thought of loading down the Mustang, queuing up a playlist, and going your own way thrill you? 

If so, you can join the leagues of road trippers who trek across America year after year. Below, we’ve outlined 15 of the best road trips, from transcontinental highways to smaller, stateside journeys. 

1. The Loneliest Road

the golden gate bridge
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If you’re taking a year off and have a mind to see all of America, you may find yourself on the Loneliest Road. 

Spanning from Ocean City, Maryland, to San Francisco, California, you can see it all. Granted, you might spend a good deal of time landlocked, but that’s okay! You’ll certainly get a gander of the heartland as you travel through 12 distinct states. 

2. The Oregon Trail

oregon, united states
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Alternatively, if you want to travel along higher lines of latitude and do approximately half the country, you could take the ancient Oregon Trail. This was the road that the pilgrims and pioneers took in creaky-covered wagons in the 1800s, offering a bit of a haunting feel. 

If you take it from Wayne City, Missouri, to Portland, Oregon, you can enjoy a nice little stay in Portland to congratulate yourself. 

Along the way, you can augment that haunting feeling and make a few of these ghost towns your pit stops. Not only will they make for great photos, they may also make for a few meet and greets from both the living and the dead. 

3. The Great Northern

seattle, washington
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If you want to move even further north, you might consider the Great Northern or US-2. This, too, gives a nod to the pioneers, but this time to the railroad that parallels part of the route.

The trick with this epic road trip is to plan it during milder months because you’re traveling all the way from Seattle, Washington to Bar Harbor, Maine – Acadia National Park. What a way to start and end what could be the greatest adventure of your life.  

4. Southern Pacific

san diego, california
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If the winter months are the only months on the table, you can still make a full-country trek a little further south. Here, you’ll make your way from Savannah to San Diego – easily, two of the best cities in the country, if not the world. 

5. Bluebonnet Trail

bluebonnets in texas
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Along the way of the Southern Pacific, if Texas steals your heart, feel free to extend your stay in the Lonestar State. You’ll have to make your way to Austin, but your road will be lined with the prettiest bluebonnets the world has to offer. Ending in Houston, you’ll be glad you made this detour off the Southern Pacific. 

5. Pacific Coast Highway

pacific coast highway
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No list of road trips would be complete without a nod to the Pacific Coast Highway. It starts all the way up in Washington’s Olympic National Park and continues for 1,650 miles until you reach the sunny shorelines of San Diego. 

Along the way, you’ll take in a wide array of American landscapes, from rainforests to near-deserts and, of course, the cliffs of the Pacific. 

To round out your journey, we have an extensive guide to 30 of the most charming spots to visit on the West Coast. 

6. The Appalachian Trail

the appalachian trail
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If, instead, you’d prefer to explore a portion of the East Coast, you might want to consider the Appalachian Trail, especially in the fall when the leaves are changing. 

You could start in the gorgeous German town of Helen, in Georgia, and travel all the way north to Monson, Maine. Along the way, be sure to make a meal out of your stay in or around the Great Smoky Mountains National Park. 

7. Blue Ridge Parkway

blue ridge parkway
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For a comparable drive, you also have the Blue Ridge Parkway. This trip really extends the beauty of the Great Smoky Mountains, as well as Shenandoah National Park. Here, you’re moving from Waynesboro, Virginia, to Cherokee, North Carolina. 

As you drive, you’ll be able to indulge in the rich tapestry of the forest, including the canopy of greenery and a wild array of animal species to meet and greet – from a distance, of course. 

8. The Atlantic Coast

seven mile bridge
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You could also consider the Atlantic Coast to spread things out further along the eastern corridor. Here, you’ll start all the way down in the Florida Keys and make your way to another famous beach, The Jersey Shore. 

ABe prepared to savor the delights of Savannah, a true Southern Belle, as well as New York City, one of the greatest cities on earth. To help you plan your pitstops, here are 30 of the most charming spots to visit on the East Coast. 

9. U.S. 1, Florida Keys

the florida keys
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If you find yourself second-guessing The Atlantic Coast, that’s perfectly alright! You can stick to the Keys, a.k.a. paradise. While U.S. 1 technically stretches from Florida to Maine, it’s perfectly acceptable to remain in Margaritaville as you move from Key Largo to Key West. 

Spend as much time here as you possibly can because every evening you pull off offers tasty margaritas, strolls beneath lighthouses, and dives amidst coral reefs – especially if you make this journey during the summer months when daylight can extend as late as 9 pm.

10. Ocean Drive

castle hill lighthouse
Image by Tripadvisor

Going back to The Atlantic Coast, if you’ve continued past the Keys, there’s a special detour worth taking – into Newport, Rhode Island. 

This is only a 10-mile drive, but it’s filled with towering seacliff mansions that date all the way back to the Gilded Age. They were once inhabited – or, more likely, summer homes – for the likes of the Astors, Morgans, and Vanderbilts. 

11. Route 66

route 66
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How many songs have been written about Route 66? And why is it so popular? The main reason might be that it offers a pretty little glimpse into the past. 

With old American diners and ancient truck stops, you can see what a small-town living in Middle America feels like. Ironically, it starts and ends in two of the biggest cities in America – Chicago and Los Angeles – while taking you through dots of desert terrain. 

12. Hana Highway

hana, maui
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From California, why not make your way down to Hawaii? You’ve certainly earned an award for your monumental achievement. People often wear the proud badge of honor that says, “I survived the road to Hana,” even though it’s hardly a trial. 

Moving from Kahului to Hana, you’ll savor the sights of insatiable sea cliffs, monk seals, and red sandy beaches. Clocking in at only 52 miles, this could be a lovely little day trip to cap off your cross-country accomplishment. 

13. Lake Shore Drive

lake shore drive
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Alternatively, you can reverse your drive along Route 66 and make Chicago your focus instead of California or Hawaii. This is only a 15-mile trek, so it’s sort of like the nightcap after a delicious day. 

Savor your feat as you take in the unique architectural creations in Chicago, from the Willis Tower to the Belle Époque beauty of Daniel Burnham’s work.

14. 17-Mile Drive

bixby creek bridge
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As long as you’re not dizzy yet, let’s reverse the drive along Route 66 again and say you end in California. If so, your victory lap there could be the 17-mile drive. Or, maybe it’s your precursor to the Pacific Highway. 

Either way, this is a delightful little 17-mile journey that loops around the world famous Monterey Peninsula. What’s wonderful about this sweet treat is that you’ll see the sea cliffs in cities like Carmel, as well as the dense green hues of the Del Monte Forest. 

May the Road Rise Up to Meet You

car on road
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There’s an Irish blessing that says, “May the road rise up to meet you. May the wind be always at your back.” Take our blessings with you, whether you’re making a local trek or a transcontinental journey. 

Wherever you stop along the way, it’s likely we already have a destination guide geared for you. Here’s hoping we meet along the highway called life! 

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