Expedia Viewfinder

21 super cool US cities, ranked

When it comes to cool, we already know that the major cities have it on lock. NYC, LA, Chicago, Boston, San Francisco—we recognize your cool cred. America’s small and mid-size cities are stepping up, giving the big metropolises a run for their trend-setting money. The cities on this list landed on our radar for interesting festivals, thriving art scenes, young and fresh demographics, and a hunger for the hipper things in life—from foodie districts to contemporary galleries. To determine the cream of the crop of cool cities to visit in the U.S., we then ranked them with the following criteria:

Scoring system:

Total possible: 28 points

Here’s our list of the coolest towns in America:

  1. Jacksonville, Florida

Photo via Flickr/Erin Murphy
Don’t let it fool you: Florida isn’t all sultry, sizzling clubs, and glistening, tanned beach worshippers. There’s also a more counterculture face to the state, and you’ll find it in Jacksonville.

Highlights:

Total score: 7 points

  1. Sioux Falls, South Dakota

Photo via Yelp/Ryan F.
With so many famous landmarks and parks surrounding the city, Sioux Falls also has its fair share of hidden gems. Come see them before everyone else discovers them.

Highlights:

    Total score: 10 points

     

    1. Chattanooga, Tennessee

    Photo via Yelp/Keith M.
    There’s more to Tennessee’s coolness cred than the music venue-strewn streets of Nashville. Sure, Scenic City is pretty to look at, but it’s got plenty of substance, too.

    Highlights:

      Total score: 10 points

      1. Grand Rapids, Michigan

      Photo via Flickr/Steven Deplo
      AKA Beer City, USA, this place knows when it’s time to let loose. Friendly, accessible, and cultured, Grand Rapids leaves more than a passing impression.

      Highlights:

        Total score: 13 points

         

        1. Laguna Beach, California


        Laguna Beach embodies every cliché of laidback California cool in all the best ways.

        Highlights:

          Total score: 15 points

          1. Duluth, Minnesota

          Photo via Flickr/Randy Stern
          Authentic, open, and super chill—if Duluth were a person, you’d definitely want to hang with her. Part outdoor enthusiast, part gallerista, she’s well-versed in good food, good vibes, and eclectic tastes.

            Total score: 15 points

            1. Oakland, California

            Photo via Flickr/PunkToad
            The city across the bay shouldn’t get all the glory. When it comes to the forefront of trendsetting food, art, music, and culture, Oakland often has San Francisco beat. It is truly one of the great cities to visit.

            Highlights:

              Total score: 16 points

              1. Bozeman, Montana

              Photo via Flickr/Kirk Olson
              Part college town, part cultural enclave in a vast wilderness, Bozeman boasts rural-grown individuality in spades.

              Highlights:

                Score: 17 points

                1. Hoboken, New Jersey

                Photo via Yelp/Brook S.
                Yes, Hoboken. Experience hipster culture-lite without drowning in a sea of cooler-than-you attitudes as in, say, Brooklyn. Yes, it’s only one square mile, but there is a lot to uncover in this compact town.

                Highlights:

                  Score: 17 points

                  1. Tampa, Florida

                  Photo via Yelp/Rob B.
                  Favorable weather and laidback vibes lend a certain easygoing something to this Florida city. See it all with a Tampa CityPASS. Or, crank up WMNF on the radio and head to Tropical Heatwave with a Cuban sandwich in one hand and a Cigar City beer in the other.

                  Highlights:

                    Score: 17 points

                    1. Santa Fe, New Mexico


                    What it lacks in size, Santa Fe makes up for in history. As the oldest capital city in the U.S., Santa Fe was cool before “cool” was a thing.

                    Highlights:

                      Score: 18 points

                      1. Amherst, Massachusetts

                      Photo via Flickr/Bart Everson
                      With three colleges in town, the population of Amherst swings toward the young and bright. Indie movie theatres, relaxed cafes, and edgy art galleries are peppered throughout town, where you can mingle with locals (43 percent of whom are ages 20-34) and pick up some tips of the town.

                      Highlights:

                        Score: 18 points

                        1. Davis, California

                        Photo via Flickr/UC Davis Arboretum and Public Garden
                        At first it may seem like just another college town, but there is a lot going on in this northern California spot.

                        Highlights:

                          Total score: 19 points

                          1. Lawrence, Kansas

                          Photo via Flickr/kansasphoto
                          Indie record stores and live shows galore, Lawrence is full to the (hipster hat) brim with rad things to see and do.

                          Highlights:

                            Total score: 19 points

                            1. Charlotte, North Carolina

                            Photo via Flickr/James Willamor
                            If art, food, and culture are on your list of musts, this city should be also. Cultural festivals abound, the restaurants scene is booming, and art is everywhere in Charlotte.

                            Highlights:

                              Total score: 20 points

                              1. Charleston, South Carolina


                              There are many reasons to visit Charleston, from the ever-expanding and exciting food scene, to the sleepy southern nonchalance that is at once friendly and cool.

                              Highlights:

                                Total score: 21 points

                                1. Seattle, Washington

                                Photo via Flickr/Ethan Kan
                                From music to fashion to art, Seattle practically was the arbiter of cool in the 90s. Though many of the decade’s fads are back, Seattle has been consistently ahead of the curve on what constitutes cool, and remains one of the most popular vacation spots.

                                Highlights:

                                  Total score: 22 points

                                  1. Iowa City, Iowa

                                  Photo via Flickr/Alan Light
                                  A city so cool, the state is named after it. But really, as the only UNESCO City of Literature in the U.S., even Holden Caulfield would admit this place is no phony.

                                  Highlights:

                                    Total score: 24 points

                                    1. Arlington, Virginia


                                    The right equation of neighborhood chill and city energy can be found in Arlington. What else could be called a perfect pairing? A delicious meal and a refreshing drink. Good thing Arlington does both to a T.

                                    Highlights:

                                      Total score: 24 points

                                      1. Madison, Wisconsin

                                      Photo via Yelp/Eric T.
                                      Live music and a robust festival season keep Madison’s social calendars chock-full throughout the year. Don’t miss a show at classic venues like High Noon Saloon, which has something on seven nights a week.

                                      Highlights:

                                        Total score: 26 points

                                        1. Austin, Texas

                                        Photo via Flickr/Heather Cowper
                                        The only uncool thing about Austin can be the weather, and it takes care of that with awesome watering holes (ahem, Barton Springs), cool places to crash (hotels like Kimpton Hotel Van Zandt), and killer cold treats (Lick Honest Ice Creams, anyone?).

                                        Highlights:

                                          Total score: 26 points

                                          What tops your list of cool places to go on vacation?