You’re itching to see more of the country but don’t want to face hordes of tourists. And you definitely don’t want to do the same old touristy things. So we compiled a list of underrated cities we think you should see. The destinations were chosen for being historically unique, trendy and cool, or just a little weird. Which one is going on your road trip bucket list?
Okay, but besides lobster, what’s up with Portland? Maine’s quintessential crustacean is a big draw, but the state is also known for its historic lighthouses (60 to be exact) along its rocky 3,478-mile coast. The oldest and most iconic is the Portland Head Light on nearby Cape Elizabeth, built during the Civil War and used as armed fortification of Portland Harbor through WWII. Five more lighthouses are within a 20-minute drive. See these famous beacons from land or water, or book a stay in the former keepers’ quarters for a singular lodging experience. This New England town also claims quaint nineteenth century architecture and cobblestone streets, historical landmarks and Victorian-era homes. Plus a lively, funky art district. But perhaps the coolest thing is the state’s largest city has a charming small-town feel.
Yes, of course the Indy 500 is reason enough to visit Indianapolis. But did you know the city is also known as one of the most haunted places in the country? The third largest cemetery in America can be found here, and serves as the final resting place to over 200,000 souls (including many Civil War soldiers), so it’s off to a spooky start. Then there’s Gravity Hill where your car will mysteriously and unexplainably roll uphill. A visit to Hannah House is another ghostly go-to, a stately red brick mansion famous for its role in the Underground Railroad where abolitionist Alexander Hannah hid slaves until a group perished in a basement fire. Whether you’re intrigued from a historical perspective or just morbid curiosity, Indianapolis may be a must-see.
Kentucky’s largest city is known for hosting the Kentucky Derby and creating baseball’s most celebrated bat. Plus, there’s bourbon. But there’s more to the city than meets the eye. Its downtown boasts the country’s second largest collection of nineteenth century cast-iron storefronts, (bring a magnet to test it out) maintaining its architectural and historical charm. You can also catch ten local attractions in the “Museum Row” neighborhood on historic West Main Street, just a block from the Ohio River. Museums here are dedicated to such subjects as the Louisville Slugger, Muhammad Ali, science, bourbon, and more. Today the area is known as one of the most interesting creative arts-inspired cultural districts in the nation.
This city played a major role in the Civil War, so it’s naturally steeped in tradition. But these days, residents are creating a new story. With more than 30 craft breweries, Richmond is home to the region’s fastest growing beer scene. No wonder it’s been called the world’s top beer destination. (Sorry, Seattle.) Of course, as one of the oldest major cities in the country, there’s plenty of history to be experienced: from the site where Patrick Henry made his famous “liberty or death” speech to the historic slave trail that chronicles the path slaves traveled to the auction blocks. So there’s something for beer drinkers and history buffs alike. Plus, don’t miss a wealth of Federal-style mansions, and museums dedicated to Edgar Allen Poe and the Civil War.
San Antonio, TX
We’re calling it the new Austin. While not the state’s cultural epicenter, San Antonio is the next up and coming star of Texas featuring chic hotels, internet-famous foods, and of course, the Alamo. With eighteenth-century Spanish flair, the city boasts attractions that blend history with modern chic. Featuring the largest Mexican market outside of Mexico, caves and caverns for adventurous explorations, the Cathedral of San Fernando (the country’s oldest, built in 1750), historic homesteads and the LBJ ranch (known as the “Texas White House”). The city is rich in history, bursting with culture, and booming with attractions both modern and olden.
Once known as the dirtiest city in America (thanks, Walter Cronkite) Chattanooga has seen a major renaissance since the early ’90s. This unsung hero of the south features the perfect balance of city life and outdoor activities. Visit Ruby Falls, the mysterious underground waterfall accentuated with multicolored lights. Or Rock City, a marvel of nature featuring ancient rock formations and panoramic views. Of course, for our diehard auto fans we would be amiss if we didn’t point out the International Towing and Recovery museum, famous for a diorama of a man being saved from a sinking car. And then there’s the famous Chattanooga Choo Choo, born as a train terminal but now a hotel, providing travelers with a comfortable stay in unique Pullman Train Cars.
With an unusually bohemian vibe for a southern town, Asheville mixes outdoor activities with more breweries per capita than anywhere in the U.S. A slightly eccentric downtown scene is vibrant with restaurants serving locally-grown food, a growing art scene starring colorful murals and street artists, and small lounges and clubs playing jazz, bluegrass and rock. Farm-to-table dinning is a big attraction, with over 250 restaurants serving locally produced meats and homegrown fruits and veggies. The city is also a mecca for golf, fly fishing, waterfall tours, bird watching, hiking and more. Or go just for the stunning view of the Blue Ridge Mountains.
Portland is proud of its motto: Keep Portland Weird. A stone’s throw from our headquarters in Seattle, it’s a destination visited often by our team. As experts of the city, we wanted to showcase some of its quirkiest activities: a 727 jetliner turned home in the woods, a hike up to Witches Castle or Multnomah Falls, the annual naked bike ride, a Bug Eaters Delight sundae at Freakybuttrue Peculiariuma and the famous food truck park. You can’t visit Portland without experiencing its famous vegetarian/vegan restaurants, the multi-cultural Saturday market, and last (but definitely not least), Voodoo Doughnut for one of their uniquely flavored fried treats (Cap’n Crunch, Tang, Vanilla Pepto and Nyquil).
Discovered by nomadic tribes thousands of years ago, the city takes pride in the famous Taos Pueblo, the only Native American living community that’s both a National Historic Landmark and a World Heritage site. Most of the buildings were built between 1000 and 1450 following the Spanish conquest of the Taos Valley. It’s also where Georgia O’Keefe and Aldous Huxley created their most famous works. Today, the historic Taos Plaza is the center for local businesses, galleries, and shops that feature American Indian arts, crafts and pottery. Restaurants offer seasonal menus that marry American Indian cuisine with Spanish influences in rustic adobe buildings. The Rio Grande Gorge Bridge is the second highest on the U.S. Highway System and boasts a spectacular lookout point.
There’s more to Savannah than just being the oldest city in Georgia, having an abundance of southern charm, oak-lined streets, antebellum mansions, historical revolutionary war sites and being the home of Forrest Gump. Savannah is possibly more affordable and laid back than Charleston, with a vibrant art community, burgeoning bar scene and picturesque beaches. They say the wine and fried pickles are better, too. Don’t leave without a riverboat cruise, trip to the beach (where bartenders have been known to hand out free shots), or stuffing yourself with extra-crispy fried chicken, fried green tomatoes, or authentic shrimp and grits.