20.) Billings, Montana
I have only been to Billings once, but it completely exceeded my expectations when I went there, because first off, I didn’t expect to see any skyscrapers when I went to Montana, and second, it actually had a lot to do for a mid size city in the middle of nowhere. After driving all day through boring Wyoming, Billings seemed like New York City to me once I finally arrived there shortly after crossing the Montana border. Billings makes my list at number 20, because for being very remote and in a state no one ever talks about, it has a lot to offer and is definitely a great pit stop city to spend a night or two in. I had one of the best cuts of filet mignon in my life at a very nice restaurant downtown called Jake’s steakhouse, then had some amazing beer right around the corner at Montana Brewery company. Montana as a state is one of the best kept secrets in the country, because it has amazing scenery, great bars and restaurants, and pretty much no crime or bad areas. Also nearby worth checking out is the college town of Bozeman, and make sure to take a ride on the Beartooth Highway, which is one of the most incredibly scenic drives I have ever taken in my life, and will lead you into Yellowstone National Park. I’m sure I will like Missoula more than Billings once I go there, but for now Billings squeezes in at #20 on my list.
19.) Reno, Nevada
Sure, Las Vegas is a fun city, but it’s little brother to the north can be just as much fun, for a fraction of the price. Nicknamed “the biggest little city in the world”, Reno has all of the lights, casinos, parities, clubs, and sloppiness of Sin City, just with a smaller skyline and price tag. Many people don’t take the time to explore other parts of Nevada besides Sin City, but the state does have more to offer. When you are coming from east to west along route 80, you will be driving for about 500 miles through absolute nothingness, so once you finally arrive to Reno, you will be very relieved, excited, and ready to get out of the car and have some fun. By no means is Reno one of my favorite cities, but I acknowledge is as a very underrated place, because Vegas gets all the attention in Nevada, and Reno often gets forgotten. Reno actually is in an excellent location too, because it is just a very short drive to Lake Tahoe, the California border, and Yosemite National Park. So, if you ever find yourself on the most boring drive in the country (I-80 across Nevada), fear not, because at the end of the state, Reno will rescue you.
18.) Omaha, Nebraska
Omaha is another city, Just like Billings, Montana, that I have only been to once but it completely blew me away and exceeded my expectations when I arrived there, because it’s another city and state that no one ever talks about or bothers to visit. Iowa is one of my least favorite states in the country, so it’s fitting that Omaha lies right on the border of Nebraska and Iowa, because as soon as you drive across awful Iowa, you reach a really fun city the second you cross into Nebraska. There is a really neat area downtown called Old Market, which has many good restaurants, art galleries, shops, and the area has a unique, historic feel to it, with brick paved streets and horse-drawn carriages. Also within an hour’s drive away is the capitol, Lincoln, which is an equally fun college town and worth checking out. There isn’t much to get excited about in the middle of the country, so Omaha is one of your best options of a city to check out if you are planning on driving cross country.
17.) Chattanooga, Tennessee
Chattanooga is one of the best small cities I have ever visited in my travels. It has a very fun downtown full of excellent restaurants, bars, and shops, the Tennessee aquarium, a river walk, and many other attractions. It’s a very walkable city, and definitely one that I like to visit anytime i’m in that part of the country. Most importantly, the city has scenery so beautiful that it should be a national park. “Rock City” which includes Lookout Mountain, Ruby Falls, and the Incline Railway, is some of the most amazing scenery I have seen in the eastern half of the country. A trip to Lookout Mountain is worth the visit to Chattanooga alone, because it is claimed that you can see 7 states from the top. Lookout Mountain is technically in 3 states itself (Tennessee, Georgia, and Alabama). Definitely put Chattanooga on your list of a city to check out during your next road trip in the southeast, you will not be disappointed.
16.) Portsmouth, New Hampshire
Portsmouth is the perfect quintessential, picturesque New England maritime town. It’s a perfect small city to take a stroll downtown and marvel at the old, historic architecture, or to enjoy views of the ocean, or for whale watching as well. There’s not much to say about this town other than it’s probably my favorite small city in New England, because it represents everything New England is supposed to represent. It’s only an hour north from Boston, so take a day trip there next time you visit Beantown, to escape the city and witness what real New England feels like.
15.) Providence, Rhode Island
A lot of the smaller cities in New England get overlooked and overshadowed since they are crammed between New York City and Boston. Providence is a perfect example of this, and is definitely a city worth checking out next time you’re in New England. The capitol of Rhode Island has a lot to offer; you can take a gondola ride on the river through downtown, or in the summer time, enjoy “Water Fire”, which is an event where 100 bonfires are lit up in the rivers through downtown, and music and other festivities are downtown as well. In addition to all of that, Providence also is home to the ivy league college Brown University, which is a beautiful campus and has a fun section near it on the top of the hill with lots of good coffee shops, stores, and restaurants. Since Rhode Island is such a tiny state, everything else is nearby, including Newport, which is definitely worth checking out as well. Next time you plan on coming to the northeast, make sure to add Rhode Island on your itinerary.
14.) Portland, Maine
I personally like to consider Maine the “Alaska of the East Coast”, because of it’s raw beauty, untouched wilderness, diverse wildlife, and because overall it’s a pretty badass state. Portland is different than the rest of Maine north of the coast, but it’s still a beautiful, fun seaside city. The Old Port district is known for its cobblestone streets, 19th century brick buildings, and fishing piers. Portland has the second highest number of restaurants per capita in the country, second to Seattle. I like Portland for a lot of the same reasons why I like Portsmouth, New Hampshire, and that’s why both made this list. It’s a shame that when most people hear the name “Portland” they automatically think about Oregon and forget about this hidden gem of a city in Maine. Portland, Oregon has plenty of reasons to go visit as well in it’s own right, but Portland, Maine deserves more attention and recognition as well, because it is an incredibly unique city worth spending some time in.
13.) Memphis, Tennessee
Memphis isn’t exactly an “unknown” city or a hidden gem, but it’s still underrated. It’s probably most famous for Elvis’s home “Graceland”, which is definitely neat and worth checking out, but that’s not why Memphis made my list. New Orleans is one of my favorite cities in the country, and Memphis is kind of like a much smaller version of NOLA. The Beale Street area in Memphis can definitely be comparable to Bourbon Street in New Orleans, and that entire area has fun nightlife, some excellent street performers, as well as live Blues music pouring out of nearly every bar on the street. For those of you looking for the excitement and party like atmosphere of the French Quarter without going to New Orleans, then Memphis is the place for you.
12.) Madison, Wisconsin
Madison, the capitol of Wisconsin, is one of the nicest college towns I have ever been to in the country, yet not many people bother to check out Madison, and go to the much less impressive Milwaukee instead. It is one of the most beautifully set cities in the US, and one of only two cities in North America situated on an isthmus (the other is Seattle), Madison is defined by its five lakes. Through a combination of factors, including the state capital and the University of Wisconsin–Madison has more to offer than might be expected from a metropolitan area of about 500,000. There are many excellent restaurants, an active theater community, lots of music, and good shopping, yet Madison is just minutes from the beautiful rural countryside. National groups and magazines rank Madison highly for being a very bike-friendly city, a great place to raise a family, having a healthy and fit population, and an overall quality of life. Madison is a melting pot of the Midwest. You’ll find professionals, students, families, hippies, musicians and everything in between. It has a vibrant nightlife scene with lots of live
music and pubs. It shares many qualities of other well-known college towns like Berkeley and Austin, a creative and educated population, but retains a small-town feel. This is one of the best cities in the midwest to both visit and live in, and yet sadly, most people never think to come here.
11.) San Antonio, Texas
San Antonio is definitely a touristy city and is well known, but it’s still underrated because it is often overshadowed by the bigger cities in Texas, such as Dallas, Houston, and Austin. There is a lot to do in San Antonio besides just the Alamo and the river walk though. The 750 foot tall Tower of the Americas has a really nice restaurant and lounge at the top, with fantastic happy hour deals. Every time I am in this city, I always go up there for a few tasty 5 dollar mango mojitos while enjoying amazing views of the skyline below. Definitely one of the best deals for any upscale lounge I have ever been to. Market Square / El Mercado has some excellent authentic Mexican restaurants as well as plenty of Mexican themed shops full of souvenirs. San Antonio is a very unique city, and no other city in Texas reflects the state’s Spanish and Mexican heritage better.
10.) Fort Worth, Texas
Everyone knows about Dallas, but the only reason why most people know about Fort Worth is because it shares it’s name with the airport. Since Dallas is so close to Forth Worth, it often gets overlooked and not many people bother to check it out. However, Fort Worth happens to be one of my most favorite small cities in the country, and has nearly just as much to offer as Dallas does. The downtown area is full of great restaurants and bars, but the real attraction to Fort Worth is the Stock Yards, a really neat section of the city a couple miles away from downtown, which has an authentic Texas cowboy feel to it. This section is full of cowboy bars, steakhouses, and shops, and has a wild wild west feel to it. Everyone here is wearing cowboy boots and hats, which is something you don’t see much of in the other big cities in Texas. They also let a few dozen cattle out on the streets in a parade of sorts twice a day, which is neat to check out. Next time you’re thinking about visiting Dallas, make sure to spend a day in Fort Worth also, it’s a completely different feel from Dallas, yet is right n its backyard.
9.) Fort Collins, Colorado
Everyone goes nuts over Boulder, and Boulder deservingly gets a lot of attention and credit because it’s a great college town in it’s own right, but the other college town about 45 minutes north barely gets any attention. Fort Collins has just as much to offer as Boulder does, and has a really fun downtown area full of excellent craft beer bars, restaurants, and shops, as well as beautiful scenery with the mountains right nearby since it’s on the foothills just like Boulder is. Many excellent breweries are located in Fort Collins also, including New Belgium, Odell, Equinox, and Pateros Creek. The people in Fort Collins tend to be friendlier than in Boulder also. Overall, I have grown to like Fort Collins more than Boulder, and next time you’re in Colorado, make sure to visit this city and you’ll also see why.
8.) Louisville, Kentucky
The Kentucky Derby may be its claim to fame, but the famous horse race isn’t all Louisville has to offer. Nestled on the banks of the Ohio River, this Southern underrated city has loads of small-town charm, a cosmopolitan riverfront district, a diverse art scene—thanks to the Kentucky Center for the Arts—and a growing foodie market with its own Restaurant Row. Sports lovers should make a stop at the Louisville Slugger Museum, while history lovers can sip mint juleps on a river cruise aboard the Belle of Louisville, a National Historic Landmark. Downtown also has a really neat area called 4th Street Live! which gives Louisville a big city feel, and kind of resembles Times Square a little bit, just not as obnoxious or tacky. Overall, Louisville is one of the best hidden gems in the county, and a city I always love coming back to visit.
7.) Washington D.C.
There’s a lot more to D.C. than just monuments, museums, and statues. Sure those are all fun and worth checking out, but definitely take some time to enjoy the other parts of the city as well. The Georgetown area has a historic feel to it and is the perfect place to take a stroll alongside the canal and shops, The Adams Morgan section is a lot of fun for nightlife, and Dupont Circle is an excellent place to relax in the park and to people watch. Also, make sure to stop by Ben’s Chili Bowl to enjoy some Chili Dogs and a half smoke, it’s one of the yummiest places to eat in the country. Nearby, Alexandria, Virginia and Annapolis, Maryland are both very beautiful, old, fun historic towns worth spending a day in. Washington D.C. is very underrated because it is famous for it’s tourist attractions and politics, but not for the things that truly make it a fun and special place to visit.
6.) Philadelphia, Pennsylvania
I struggled to put Philly on this list, because a part of me doesn’t think it’s underrated, but at the same time, I feel it is, because most people rightfully and justifiably think the city is, for lack of a better word, a shithole. And most of the city is, in fact, a dumpy ghetto, and I used to hate Philly as well. But the more times I kept coming back here, the more I fell in love with it. This city has a lot of bad parts, but it also has some really fun sections if you know where to look. First off, it is one of the best food cities in the country, no stop in Philly is complete without a trip to Geno’s for a Cheesesteak. Also, the Reading Terminal Market downtown is one of the best city markets I have been to, and definitely better than the more famous Quincy Market in Boston. In addition to the food, Philly has some fun nightlife as well. A stroll up and down South Street is always fun, and one of my favorite bars, the Darkhorse Bar, is right around the corner from there. Other fun sections include Penn’s Landing and Northern Liberties. The Liberty Bell and Constitution Hall are definitely worth checking out (because they are free), but there’s much more to do in Philly than the tourist attractions. Just make sure to stay in the good areas, and you’ll learn to enjoy this city as much as I have.
5.) Savannah, Georgia
Savannah is a well known city, but still not enough people care to visit it. It is one of the most beautiful cities in the country, and with a beautiful Spanish moss tree lined park nearly every block, it has more parks than any other city in the country. Savannah is one of the best examples of southern architecture and charm. River Street is a popular cobblestone street worth checking out along the bank of the Savannah River, and Chippewa Square is where the famous scenes of Forrest Gump were filmed where he’s sitting at the bench waiting for the bus. The best thing about Savannah is just to walk up and down its streets and enjoy the beautiful architecture and trees all around. Nearby is Tybee Island which is a perfect beach getaway to spend the day in. If you’re stressed out or need a break from a big city, come to Savannah and all of your problems will ease away.
4.) New Haven, Connecticut
I know I’m being a little hometown biased here, but my home city definitely deserves more recognition than it gets. It gets almost no attention since it’s in between New York and Boston, yet New Haven is honestly one of my favorite cities in the country. New Haven is so underrated, that a lot of people even in Connecticut do not bother to go to it! The entire area downtown near the Yale University campus is full of amazing restaurants, fun bars, beautiful gothic style architecture, unique shops, and impressive museums. In addition to all of this, New Haven is one of the best food cities in the country, and has so many good restaurants, that I feel it can compete with cities 10 times its size in that department. It’s right up there with San Francisco, Chicago, and Philly in terms of good eats. The best pizza in the country can be enjoyed after waiting in a long line at Pepe’s, and the first burger was invited at Louis Lunch, which is also very delicious and is in a neat, historic little building. One of my favorite mexican restaurants, Viva Zapata, is also here and has amazing cheese enchiladas. Mamouns is also a great place for a late night snack and has fantastic falafels and fresh mango juice. Since Yale is here, there is a ton of diversity and culture in the city. These are just a few of the dozens of amazing and unique restaurants New Haven has to offer. There’s also great Asian, Ethiopian, and Italian food, as well as a couple great steakhouses and burger joints. Also, New Haven is on the coast, so you’re just a short drive to some great beaches and views of the Long Island sound, or enjoy a view of the skyline from the top of East Rock park. I’m proud to call New Haven my home, and I’m kind of happy that it is a hidden gem that more people don’t know about, because that means I get to enjoy it more without it being overcrowded.
3.) Indianapolis, Indiana
Peyton Manning may have put Indianapolis on the map, but Indiana is still far from a tourist destination that people think to come visit. Both Forbes and Livability.com rank Indianapolis as one of the best downtowns in the United States citing “more than 200 retail shops, more than 35 hotels, nearly 300 restaurants and food options, movie theaters, sports venues, museums, art galleries and parks” as attractions. The Mass Ave. area is a great area full of nightlife, and is home to a great jazz bar called Chatterbox. The Broad-ripple section is also full of fun bars and nightlife, and less than an hour away is the town of Bloomington, one of my favorite college towns in the country and the home of the University of Indiana. Indiana is one of the last states people ever think about taking a trip to, but if you’re going to road trip to Chicago, Indianapolis is only a few hours away and definitely worth spending a day or two in.
2.) Columbus, Ohio
Columbus is the perfect mid size city in my opinion. Most people think of Cleveland or Cincinnati when they think of Ohio, but Columbus is actually the best and most fun city in this state. It has several different sections, all of which are equally fun. It is home to Ohio State University, which has one of the biggest campuses in the country, and a very fun college town area next to the campus. The city also has a German section which has cobblestone streets and some of the best German food I have had in the country. And of course the downtown area has tons of great restaurants and bars also, and has the feel of a big city. Columbus is one of the best cities in the midwest, and one that hardly anyone ever talks about or visits.
1.) Salt Lake City, Utah
Salt Lake City makes my list as the most underrated city in the country for many reasons. Like many other small cities that I had visited for the first time, I had zero expectations for SLC when before arriving, but once I got there, I was completely blown away with how much I fell in love with the city. To me, it is the perfect city to settle down and raise a family in. It has the perfect mix of everything. If you’re looking for the best nightlife in the country, then Salt Lake City probably isn’t the city for you, but if you’re looking for a nice balance of everything, then this place is perfect. For being a pretty small city, it has a big city feel downtown, and has some amazing modern shopping and dining areas, plus the best bars and nightlife you’ll find anywhere in Utah. It is one of the safest cities I have ever been to, and I can walk around downtown any time of night by myself without feeling in danger at all. It is also one of the most scenic cities in the country, and is surrounded by beautiful mountains as well as the nearby Great Salt Lake. Some of the best skiing in the country is just minutes away from downtown, including the very beautiful ski town of Park City. Unlike the rest of the state, the Mormon religion is not really as in your face here, since half of the population isn’t Mormon, and that is clearly evident by the presence of bars, breweries, and nightlife. And you’re just a short weekend trip away from all of the beautiful National Parks southern Utah has to offer, including Arches, Bryce Canyon, Zion, and Canyonlands. Salt Lake City is one of the cleanest, safest, scenic, and most fun small cities I have ever been to. When I was in my late teens or early 20’s, I probably wouldn’t have appreciated SLC as much as I do now, but I think Salt Lake City would be an excellent choice of a city to settle down in, because it’s the best of all worlds, you get the city feel and life without the price tag or traffic of being in a big city, you get the incredibly scenery and nature all around you, and you get the safety and security of being in great neighborhoods. For all of these reasons, SLC is the best hidden gem in the country.