15 Underrated Cities for Your Great US Road Trip

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Getting off the Beaten Path on a US Road Trip

When it comes time to plan any US road trip, there are cities and landmarks that immediately leap out as ‘must see’ inclusions.

The likes of New York City, Las Vegas, Los Angeles, Chicago, Miami, Washington DC, and Philadelphia automatically earn their place on your itinerary just as surely as the Grand Canyon, Yellowstone, and Yosemite claim a day or three.

While these cities and landmarks are sure to be highlights of any US road trip, there is a host of other cities that are just begging to be explored and experienced.

From hipster-friendly craft beer heavens to hiker’s paradises to charming New England escapes, there is far more to any US road trip than the obvious. Below, you’ll find fifteen underrated cities worthy of a day, a weekend, or even a week on your itinerary.

15 Underrated Cities for Your US Road Trip

There’s never a dull moment on a road trip.

Some of the most memorable experiences on my 2016 Great US Road Trip occurred in towns I never even thought about in planning the trip.

From getting the death stare in a West Texas burger joint to visiting the Roswell Museum to boozy wine tour days in southern California, even the shortest pit stop made for an unforgettable memory.

Looking for a hidden gem to add to your US road trip? Here, you’ll find fifteen cities that don’t get the credit they deserve.

greenville carolina
Image courtesy of James Willamor.

#15 – Greenville, South Carolina

The Carolinas don’t tend to get a lot of love when it comes time to plan a US road trip. Without the world-famous landmarks or bustling cities to draw people’s attention, both North and South Carolina are often missed, and it’s a crying shame.

Take Greenville, for example. A dynamic foodie city with small town charm in spades, Greenville well and truly lives up to its name with an abundance of nearby hiking trails and the famous Swamp Rabbit Trail – a former stretch of rail that has been converted into a stunning cycling route.

But it’s as a food destination that Greenville has earned its plaudits, and every ‘reasons to visit Greenville’ article you’re likely to find will rattle off so many restaurants that you’ll want to devote a week to this charming corner of the States.

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While I haven’t made it to Greenville myself, Feast and West has a great piece on why you’ll love Greenville.

Annapolis Maryland
Image courtesy of m01229

#14 – Annapolis, Maryland

Maryland is often overlooked in favour of its more prestigious neighbours such as Pennsylvania, Washington DC, and New York.

The allure of a day in the Big Apple, the City of Brotherly Love, or the US Capitol is obvious, and I would never suggest something as crazy as cutting one of the East Coast Three to make room for Maryland.

While many might favour Baltimore, I found myself just a little bit in love with Maryland’s capital, Annapolis.

Why Annapolis?

Located on the shores of the mighty Chesapeake Bay, Annapolis is a city that well and truly embraces its proud naval tradition.

Whether you’re out on the water sailing, paying a visit to the US Naval Academy, feasting on blue crab at Cantler’s, or just soaking in the capital’s rich history, Annapolis is a cute little city that is a great break from the bigger and busier cities you’ll doubtless visit while on the East Coast.

The city might not be awash with landmarks you’ve daydreamed about since your youth, but it’s possessed of a quiet charm that is hard not to love.

I spent two sunny weeks in 2012 exploring Annapolis with a local; soaking in the sun on the waterfront, eating my fill of Maryland’s signature blue crab (with lots of Old Bay), and enjoying its laid back nightlife.

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While I never wrote about my experience in Annapolis, it’s also a short drive from the East Coast’s popular seaside playground, Ocean City.

bixby bridge monterey california
Bixby Bridge has got to be right up there with the Golden Gate and Sydney Harbour as one of the most visually stunning bridges on earth.

#13 – Monterey, California

The drive down California’s Pacific Coast Highway is one of the most breathtaking stretches of road you’re likely to ever encounter.

Stretch from San Francisco all the way down the windswept, craggy coast, Route 1 has featured on two of my previous US road trips and stands out as one of the absolute highlights.

Located not too far from San Francisco, quaint Monterey is a seaside town with a lot of charm.

From the world-famous Monterey Aquarium to saltwater taffy and fresh seafood on the waterfront to gorgeous Carmel-by-the-Sea to its proximity to picturesque Bixby Bridge, Monterey is a stop every Pacific Coast road trip should include.

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Interested in Monterey? You can read more about how to spend two days in Monterey.

flagstaff arizona
Image courtesy of Nicholas A Tonelll

#12 – Flagstaff, Arizona

Flagstaff doubtless makes it on to a lot of US Road Trip itineraries due to its proximity to the Grand Canyon.

A popular base from which to explore the iconic Grand Canyon, Flagstaff is a charming city of its own. It has a great hipster mountain town vibe to it that is hard not to love, and it would be criminal to leave Arizona without having given a little time to Flagstaff.

More than just the Grand Canyon

Many picture Arizona as dry desert, but Flagstaff’s location in the mountains means it gets downright chilly in the winter. The cool mountain air makes for world-class stargazing, and the Lowell Observatory is a must for anyone with a love of the night sky.

The town itself is awash with brew pubs and brunch joints (my personal favourites are Beaver Street Brewery and the Toasted Owl Cafe, and it’s perfectly located to visit a number of national parks and landscapes such as Petrified Forest National Park, Meteor Crater, and Walnut Creek Canyon.

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Everybody has been to the Grand Canyon, but have you ever explored the Indian cave dwellings at Walnut Creek Canyon? I have, and it was fascinating.

abq albuquerque balloon festival
Image courtesy of Larry and Linda

#11 – Albuquerque, New Mexico

ABQ might be best known for its role as the backdrop to Walter White’s crystal meth empire onĀ Breaking Bad, but there’s a lot more to the New Mexico city than the often oppressive way it was portrayed in the AMC hit.

While my own US road trip featured Sante Fe instead of ABQ, there are plenty of reasons to visit Albuquerque including their world-famous Hot Air Balloon Festival.

Located along iconic Route 66 and home to some of a unique melting pot of Hispanic, Native American, Latino, and Anglo culture, this is truly the US Southwest epitomised.

Whether you’re hiking the surrounding desert, visiting Native American desert dwellings, eating your fill of delicious chili, or just taking a spin out on America’s most famous stretch of road, Albuquerque is more than just a quick stop for gas.

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Lonely Planet has plenty of ideas when it comes to things to do in ABQ.

Image courtesy of Karah Levely-Rinaldi

#10 – Moab, Utah

The name might not immediately leap to mind when you’re thinking of dream US destinations, but take a look at Moab’s location on a map and you’ll see why it’s a must have in my eyes.

Located at the crossroads between Canyonlands National Park and Arches National Park, Moab is the perfect launching point from which to explore these two stunning national parks. For those with a love of the great outdoors, there are few places better suited.

For adrenaline junkies, you’ve got white water rafting, rock climbing, skydiving, ATVing, and mountain biking to keep you occupied. For the more sedate, simply hiking these iconic parks is a once in a lifetime experience.

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Utah was a last-minute cut from my most recent US road trip, but Hike Bike Travel has a fantastic Moab itinerary that ought to inspire.

asheville pisgah forest blue ridge mountains
Image courtesy of Jeff Gunn

#9 – Asheville, North Carolina

It’s probably not a well-kept secret anymore, but Asheville in North Carolina is the one city I was most disappointed I missed in my most recent road trip. Named as Lonely Planet’s #1 destination in the US in 2017, Asheville is a city on the rise.

A foodie and beer lover’s heaven, Asheville has captured the hearts of most anybody who has had the wherewithal to add it to their itinerary.

With a thriving arts scene and access to the nearby Blue Ridge Mountains for hiking and day trips, Asheville is a city I am determined to get to and thoroughly explore just as soon as I can.

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You can read a little bit more about Asheville and seven other cities I was sad to miss in my article 8 Places I’m Sorry I Missed on my US Road Trip.

portland maine lighthouse
Image courtesy of Roger Goun

#8 – Portland, Maine

I’ve had an enduring fascination with the New England ever since I got my hands on my first Stephen King book. The seminal horror writer has based a great many of his novels in his home state of Maine, and Portland perhaps best exemplifies the New England aesthetic.

Cobblestone streets, salty breezes, a lonely lighthouse, clam chowder, ice cold beers, and that unmistakable New Englander personality all blend together to make Portland the quintessential coastal New England town.

You half expect a haunted mist or time-eating Langoliers to come looming up out of the morning fog…

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The New England continues to elude me, but Travel and Leisure has a great three day Portland itinerary to get you inspired.

savannah georgia
Image courtesy of Predl

#7 – Savannah, Georgia

My own US road trip featured the underwhelming city of Atlanta, so I’m a little disappointed when I read more and more about why Savannah is the best place to go to experience true Southern comfort and hospitality.

Shaded by gorgeous oak trees, the classic Colonial architecture of this fading Southern Belle speaks of a different time in American history. With amazing food, oodles of history, and that all-important southern hospitality, Savannah is a city I am dying to visit and you should be too.

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While I was busy being disappointed by Atlanta, Adventurous Kate was falling in love with Savannah. You can read her reasons to love Savannah here.

page arizona horseshoe bend
Image courtesy of Petr Melssner

#6 – Page, Arizona

On the shores of gorgeous Lake Powell and set amid some of the most stunning scenery the American west has to offer, Page is your gateway to unforgettable sights such as Antelope Canyon and Horseshoe Bend – two of the most photographed landscapes in all of America.

Whether you choose to take in this remarkable scenery on foot, on a Colorado River cruise, or from a kayak – it’s a corner of the US that should be on any respectable cross-country road trip.

With a huge variety of Page hotels to choose from, visitors can do the backpacker thing or live in the lap of luxury as they explore the canyons, cliffs, and windswept desert at their own pace.

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Page was another last-minute cut from my Great US Road Trip, but you can read plenty of reasons to visit Page, AZ over at Miss HappyFeet.

niagara falls buffalo ny
Image courtesy of Greg Knapp

#5 – Buffalo, New York

New York State inevitably ends up on every US road trip, but more often than not, it’s just New York City that gets a few days assigned to it.

The American gateway to Niagara Falls, Buffalo is more than just a place to base yourself ahead of a ride on the Maiden of the Mists. Like the other underrated US cities on this list, it’s a thriving foodie scene that has plenty to keep your taste buds occupied for a weekend or more.

Travel and Leisure named Buffalo as America’s third most underrated city in 2016, citing the city’s thriving craft beer scene, it’s perfect pizza, vibrant arts scene, and jam-packed festival calendar as reasons why the city warrants a visit.

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The Crazy Tourist has fifteen reasons to visit Buffalo that might get your imagination in overdrive.

durant lake raleigh nc
Image courtesy of Russell Harrison

#4 – Raleigh, North Carolina

You’ve got to be a pretty remarkable city to capture the hearts of Caz & Craig from yTravel, but that’s exactly what Raleigh, North Carolina has done. The jet-setting family of four have singled out Raleigh as their favourite spot in the US and even have a fantastic guide on how to move to Raleigh.

Why do they love it so? It’s a cruisy, green, modern, hip city with stunning natural beauty to pair with its thriving food, beer, and arts scene – the kind of place whose charm is apparent from the moment you enter its city limits.

To me, Raleigh’s food and beer scene is one of its biggest appeals, and it might be best for my waistline that I wasn’t able to make it in my 2009, 2012, or 2016 road trips…

A city with small town charm, there are plenty of cheap Raleigh hotels to make it a good stop on your trip north (or south), but why not spend a few days between Raleigh and Asheville to really see what North Carolina has to offer?

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Rebel Heart Travel has come up with fifteen things to do in Raleigh that ought to inspire. Go check them out!

broadway honky tonks nashville
Image courtesy of spablab

#3 – Nashville, Tennessee

Music City is a must-see for country music lovers, but the Tennessee city is an often overlooked gem when it comes to US road trips.

While it may not have the same drawcard appeal as New Orleans or Florida, there’s plenty of reasons why Nashville should feature in your exploration of the US South.

Country music may not be your cup of tea, but you haven’t partied until you’ve spent a night sipping Bud Lite and bouncing from honky tonky to honky tonk in Nashville. With live music in every bar and people singing along to their old favourites, it’s hard not to get swept up in the atmosphere.

Just steer clear of those cheap Fireball shots…

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I recently discussed whether Nashville or Memphis is the more deserving road trip destination.

portland oregon
Image courtesy of Twelvizm

#2 – Portland, Oregon

The premier hipster haven in North America, Portland is a city that well and truly embraces its weirdness.

One of the only places I’ve made a point of visiting on multiple occasions, Portland’s craft beer scene, food scene, and overall atmosphere of general weirdness makes it the kind of city I’d love to call home someday.

Why Portland?

Beer lovers will be spoiled for choice by the city’s dizzying array of craft beers, and the opportunity to design your own Portland brewery tour is a fun way to get out and explore.

Add in the presence of the nearby Colombia River Gorge and the gorgeous Pacific Northwest coastal towns such as Astoria and Tillamook, and you’ve got a recipe for a city that well and truly surpasses all expectations.

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I’ve waxed lyrical about Portland on many occasions, most recently when I compared it to Seattle and Austin in my Hipster City Showdown.

pretty girl road trip
My friend, Kait takes the wheel during a SLO wine tour. I’m really stoked with how this photo turned out.

#1 – San Luis Obispo, California

I’d never evenĀ heard of San Luis Obispo (henceforth known as SLO) until my friend, Kait suggested I swing by on my way from San Francisco to Los Angeles.

I certainly never would have guessed that SLO would go down as one of my favourite stops on the entire road trip.

Wine tasting, bar crawling, and delicious food devouring were all on the agenda in this sunny, youthful college town.

If you’re looking to fully embrace Southern Californian life in a hidden gem that hasn’t been ruined by tourists yet, you could do a lot worse than SLO.

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I’ve written before about the many reasons to visit SLO.

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