5 Unexpectedly Awesome Cities to Explore on Your Next Road Trip

Since domestic travel is here to stay for the foreseeable future it’s time to start planning summer road trips. According to Expedia’s Traveler Sentiment Study, 62% of global travelers took or would be willing to take, a road trip during the pandemic. So where are people going? Here are five of Esquire’s unexpectedly awesome domestic cities to explore on your next road trip and a few reasons why these cities are a good choice for a first-time return to travel after the pandemic.

1. Chattanooga, Tennessee

Chattanooga is the Scenic City in Tennessee that everyone is chatting about. It’s caught a lot of attention of remote workers since it boasts the fastest internet connection in the world and has a lot to offer for adventurers and downtown enthusiasts. Adventurists should visit The Sculpture Fields at Montague Park, which is a 33-acre landfill turned international sculpture park that features more than 40 large-scale contemporary works to take in. Plus, a brand new 25-mile Riverwalk is nearly complete nearby the CHI Memorial Stadium where the Chattanooga Red Wolves play. After you get your adrenaline pumping by visiting one of the country’s oldest hang-gliding schools at Lookout Mountain Flight Park, head downtown to experience an innovative testing ground for new dining concepts at Proof Bar & Incubator or the city’s first rooftop bar, Whiskey Thief. If you’re looking for a balance between downtown vibes and adrenaline-pumping adventure, Chattanooga is the city to see.

Where to stay: The Hilton Garden Inn Chattanooga Downtown Hotel, The Westin Chattanooga , or Chattanooga Marriott Downtown.

2. Tucson, Arizona

Tucson, Arizona’s second city, is where the food is as delicious as it is diverse. Foodies driving through famous southwest freeways can find comfort on every corner in this designated UNESCO City of Gastronomy. Phoenix Magazine recently said its top-notch Sonoran-style cuisine should be on every traveler’s bucket list. But grub isn’t the only thing this desert city has going for it. Get a true taste of Tucson by trekking through Saguaro National Park where Saguaro cacti grow up to 40 feet tall and live for centuries. Park visitors can view the iconic treelike cacti along the eastern and western limits of the park via hike or drive. Plus, this otherworldly desert is home to the best stargazing spots and the Arizona-Sonora Desert Museum, which has one of the world’s most comprehensive regional mineral collections, more than 200 different animal species and 98-acre sanctuary.

Where to stay: JW Marriott Tucson Starr Pass Resort and Spa, Loews Ventana Canyon Resort or Joshua Tree House Tucson.

3. Milwaukee, Wisconsin

Milwaukee is a great city on a great lake located in southeastern Wisconsin, just an hour away from Chicago. Make the most of your time in Milwaukee because when the weather gets warm, this Midwestern metropolis comes alive with something for everyone: music festivals, beer gardens and so much more. Music lovers can check out Summerfest, the world’s largest music festival, on the shore of Lake Michigan. For a more relaxed local live music vibe, Chill on the Hill in Humboldt Park is also a hit every Tuesday. Brew city is also the place to be for beer lovers with authentic outdoor options like The Bavarian Bierhaus, The Beer Garden at the Deer District, Estabrook Park Beer Garden and Hubbard Park Beer Garden. When you want to get a taste of the city and don’t have the sit-down time, you’ll find a variety of food trucks at almost every summer event here. From Zocalo Food Park to Food Truck Friday near Red Arrow Park downtown, a local Milwaukeean startup made it easy to find food trucks on the streets of Milwaukee by time and location on this app. Art lovers can head to the Milwaukee Art Museum or explore city streets that transform into an open-air art gallery every year thanks to Sculpture Milwaukee. Plus, travelers of all abilities can enjoy Milwaukee’s natural beauty and attractions thanks to free beach wheelchair rentals at Bradford Beach, sensory-friendly performances at First Stage, the Milwaukee Ballet, accessible transit on The Hop and more.

Where to stay: DoubleTree by Hilton Milwaukee Downtown, Hyatt Place Milwaukee Downtown, or Saint Kate Arts Hotel.

4. Bend, Oregon

Bend is Oregon’s outdoor playground that should be on every road tripper’s radar. It’s a great spot for family-friendly fun, outdoorsy adventures and where beer drinkers can imbibe. For family-friendly fun in the outdoors, scale boulders in Smith Rock State Park or go night canoeing on the iconic Cascade Lakes. Plus, you can’t miss hiking Pilot Butte, a dormant cinder volcano or the 5.5-mile Sun-Lava path in Deschutes National Forest at the Newberry National Volcanic Monument. Back in the day, Bend was a logging town and now they’re a lager town – and porter, and IPA. For beer enthusiasts on a mission to leave no keg untapped, pedal along the largest beer trail in the West on the 22-stop Bend Ale Trail. This trail covers seven territories in one ale trail and is home to more than 24 distilleries, cideries, wineries and kombucha brewers. If you’re looking for a more laid-back, simple pleasure approach on your trip to Bend, blend in a walk around one of their 80 public parks or stroll through bustling shopping districts.

Where to stay: The Lodge at Eagle Crest Resort or LOGE Bend’s dog-friendly inn.

5. San Antonio, Texas

San Antonio is the Texas town that invites visitors to discover what’s old and explore what’s new. Here you can walk, bike, hike and play through spectacular parks, green gardens and outdoor spaces filled with modern attractions and historical landmarks. Plan a picnic and feed ducks at Brackenridge Park or explore magical Texas Hill Country Views at Enchanted Rock State Natural Area. And don’t miss The Japanese Tea Garden that features a lush, year-round garden and floral display with shaded walkways, ancient stone bridges, concrete sculptures and a 60-foot waterfall and ponds filled with Koi. The creative community in Ol’ San Antone is always evolving when it comes to creating authentic experiences for history buffs, arts and culture aficionados to explore. Visit marketplaces with modern European and American art at the McNay Art Museum or go where nature, science and culture meet at The Witte Museum. Rediscover the gem of Texas history by strolling through the Alamo that features interactive tours and exhibits and hosts reenactments of the Texas Revolution. San Antonio is one of America’s fastest growing cities and is eager to inspire travelers to check boxes they didn’t even know existed.

Where to stay: Grand Hyatt San Antonio Riverwalk, The St. Anthony, a Luxury Collection Hotel San Antonio, or Hotel Emma.

Let us know where you’re heading on your next road trip in the comments below!