The Coolest Small Cities in the U.S.
Plan your next weekend trip—or your next move.
In 2021, it’s become a classic story: One of your good friends decided to give up the hustle and bustle of the big city and move somewhere a little more low-key. “I want cheaper rent,” they said, “maybe even a yard.” You were skeptical—that is, until you went to visit.
Across the US, you’ll find smaller cities that offer all the trappings of a small town—fresh air, tree-lined streets, plenty of opportunities to use the word “quaint”—with enough culture, bars, and restaurants to keep up with the big boys. The sweet spot, we figure, is somewhere under 100,000 people — who we can only assume will welcome you to town and swiftly point you to their favorite neighborhood dive and the bartender to ask for.
Visit any one of these small cities and you can pack your itinerary with gorgeous hikes, award-winning brews, knock-out restaurants, quirky art shows, and fun things to do that go waaay beyond antiquing. You may even find yourself thinking, “Hey, I could get used to this,” and stay awhile.
If you thought you knew the desert, think again
If you’re ready to unpack your preconceptions about Arizona—namely, that it’s a barren expanse of lonely cacti and dusty highways—make a beeline for Flagstaff. It’s home to a 1.8 million acre pine forest, a nearly 7,000-foot tall mountain at Humphreys Peak, and the state’s largest ski resort. Yes, you heard that right: Snow. In the desert.
Where you might expect to find two seasons—blistering summer and sub-zero winter—you’ll actually get all four. In the warmer months, delve into the world’s largest stand of ponderosa pines in Coconino National Forest, or venture out onto any number of epic trails—the best being the Kachina Trail, where you’ll descend lava cliffs and forested canyons, and the Abineau-Bear Jaw Loop, from which you can peep the Grand Canyon 70 miles away. When the temps dip, hit the slopes of the Arizona Snowbowl, where we’re sure you’ll be more than satisfied by the 260-inches of annual snowfall, 55 runs, and ample opportunities for apres-ski showboating.
Must eat & drink: The Monte Vista Hotel has been open for almost 100 years, and has the ghost stories to prove it. Sip cocktails with specters in the hotel’s popular Rendezvous Bar. Flagstaff is Arizona’s craft beer hub, with joints like Mother Road, Historic Brewing, and Proper Meats + Provisions there to hold you down.
Ditch Portland for this fast-growing, free-spirited mountain town
Removed by hipper-than-thou Portland by three hours and a snowy mountain range, Bend is a city of contradictions. It's a ski town that’s also known for white-water rafting, boozy river floats, and high-desert ranch life. The laid-back, artsy downtown — cut through serenely by the mighty Deschutes River — manages to give off immaculate small-town warmth despite the fact that the city’s sprawl has pushed it to some 100,000 residents. It’s an ever-growing mix of cowpokes and creatives; college doofs and career bartenders; free-spirited artisans and hardy agrarians, all here to enjoy the scenery and some of the PNW’s best restaurants.
Must eat & drink:Deschutes Brewery has been at the forefront of craft innovation since the glory days of 1988, and it hasn’t missed a beat. Grab a pint of Mirror Pond pale (or jet-black rarity the Abyss, if you're lucky) at its downtown taproom. Other standouts among Bend's 20+ breweries include Ale Apothecary, Crux and Cascade Lakes. Stave off any after-effects with Peruvian steak stir-fry and catfish tacos at Spork, or go old-school at downtown's The Drake. The fancy diner vibes belie gut-busters like a hot-honey fried chicken and a locally sourced ribeye doused in bone-marrow butter.
Don’t leave without: Jumping in the Deschutes. There are few more refreshing ways to shock the toxins out of your body after a long day of getting to know the city. — Andy Kryza
Greenville, South Carolina
A revitalized community where culinary and creative arts abound
You might assume South Carolina’s best small city is found along the coast, but head inland and you’ll find it’s true rising star. Just 1.5 hours down the road from Asheville, the city of Greenville quietly boasts an active arts community, burgeoning culinary scene, and easy access to some downright spectacular natural beauty.
Let your first impression be Falls Park on the Reedy, a 32-acre park smack in the middle of downtown that includes a 60-foot waterfall and the 345-foot Liberty Bridge. This is also the best jumping off point to the Swamp Rabbit Trail (more on that momentarily). The relatively cheap rent in Greenville has spawned one of the South’s fastest-growing arts scenes, which in turn has spurred the creation of festival after festival; depending on when you visit, you might find yourself mingling with creative types at Artisphere, Euphoria, and Fall for Greenville. The neighborhood of West Greenville is an art hub in and of itself, and throughout the city, you’ll find more than 95 public works of art, including Dale Chihuly’s Rose Crystal Tower.
Must eat & drink: The walkable, bikeable 22-mile Swamp Rabbit Trail is lined with good eats; try Soby’s or, further out, Swamp Rabbit Café & Grocery. There’s also Gather, a food hall made from repurposed shipping containers where you’ll find indulgent goodies from all across the country, including fried chicken and donuts, Miami street food, and Maine lobster rolls.
Don’t leave without: Venturing out to a state park—whether that’s Paris Mountain, Caesars Head, Table Rock, or Jones Gap—to take in views of sweeping lakes, forested mountains, and thunderous waterfalls.—Jay Gentile
Michigan's next "it" destination
Muskegon is one of the best beach towns in the Great Lakes State. But it stands out from the myriad charming, sand-dusted hamlets that dot Michigan’s coastline simply by having, well, people. A short drive from Detroit and Grand Rapids, and a damn-lovely day trip away from Chicago, Muskegon hums with art, music, and great food. No wonder everybody's calling it Michigan's next "it" destination.
Still, none of that would matter without the beaches. That's why you're here, and trust that they are magnificent. The crown jewel here is Pere Marquette Beach, one of the Great Lakes' best maintained patches whose white sands and azure waters look almost Caribbean (except, of course, when they're frozen). The requisite beach activities are all here—sailing, fishing, swimming in a giant body of water without worrying about sharks. Oh, and Muskegon has an amusement park! Michigan's Adventure is smaller scale than, say, Cedar Point, but the very fact that there are good coasters and a big-ass water park in this lake town is astounding.
Must eat & drink: Get your requisite lake perch on the waterfront at the old-school Lake House and your Michigan beer fix at Pints & Quarts. During summer, The Deck, right on Pere Marquette beach, combines great drinks and live music to claim status among America's best beach bars.
Don't leave without: It's not like you're not gonna take a photo of the South Pierhead and South Breakwater lighthouses, so might as well take a tour too. —Andy Kryza
Welcome to the world’s biggest little beer town
A mere 12 miles from Denver, Golden will instantly remind you that Colorado was once the Wild West. Besides its well-preserved Old West charm—including Colorado’s longest standing saloon dating back to the gold-mining era—this town is also home to some of the Centennial State’s best breweries and trails, overlooking the Front Range.
Clear Creek serves as Golden’s center of activity. During summer, rent a tube from Adventure West and join the kayakers and paddle boarders navigating the rapids at the White Water Park with views of neighboring peaks Mt. Zion and the Table Mountains. You can also borrow a free ride from the Golden Bike Library, cruising the smooth bike path that runs all the way to Denver and west through Clear Creek Canyon, where rock climbers dangle from sheer walls and hiking trails abound.
Must eat & drink: Try breakfast at the long-standing Windy Saddle Café, authentic Nepalese at the Sherpa House, or an elk cold cut sandwich at D’Deli. And don’t miss some of the new food halls: There’s Tributary, with 10 tasty vendors to choose from, and the 360-degree-view roof deck at The Golden Mill. You’ll be hypnotized by the contraptions used to make cocktails at the Eddy Taproom, which also serves slow-cooked meats and decadent milkshakes.
Don’t leave without: Drinking beer. Golden is known as the “world’s biggest little beer town,” thanks mostly to resident monster brewery Coors. But Golden’s eight craft breweries must also be duly noted—namely, New Terrain, which serves some of Colorado’s tastiest suds, plus free live music at the base of North Table Mountain, and Golden City Brewery, situated in the backyard of its founders’ historic downtown home. –Shauna Farnell
Ithaca, New York
Galavant past antique houses and 150+ waterfalls
Population: ~31,200 (~60,000 when class is in session)
Home to three universities, Ithaca may seem like just another college town—but there's a lot more to it than Andy Bernard would have you believe. You can enjoy bars and farm-to-table restaurants, catch a theatrical performance or a live outdoor concert, and shop to your heart's content without feeling like you've put 30 miles on your legs. Admire the antique houses in the historic neighborhoods like East Hill and Cornell Heights, then stroll down colorful, tree-lined streets downtown.
Lazy afternoons can be spent following lush trails and crossing historic bridges leading to gorges and lakeside views not far from the city center. Chase waterfalls—there are 150+ of them within 10 miles of downtown—which demand to be photographed before diving in. Take in the sunset over Cayuga Lake from Stewart Park, where you will inevitably wonder why you didn't come to Ithaca sooner.
Must eat & drink: Sample upscale Italian at Gola Osteria or wood-fired pizza at Ciao!, then prepare to get crisp: With the highest density of craft cideries in New York state—10 within a 30-minute radius—your first drink should probably come from an apple. Head to Finger Lakes Cider House, and if you're visiting in early fall, you can hit up the annual Cider Week. Meanwhile, you're smack in the middle of Finger Lakes Wine Country, which boasts over 200 wineries, distilleries, and breweries.
Don't leave without: A hike through Taughannock Falls State Park leads to a 215-foot waterfall roaring off cliffs that tower nearly 400 feet above the gorge. —Carol Cain
The mountain town poised to be the next Boulder, Colorado
Bozeman has long flown under the radar—but not for much longer. Home to Montana State University, you’ve got laid-back college town vibes paired with Western small-town charm and a touch of big-city culture, like the Museum of the Rockies and iconic music venue The Rialto. It's an immediate charmer thanks to its gorgeous mountain setting and walkable downtown district.
Did we mention the outdoors? There's skiing, with Bridger Bowl 30 minutes away and the larger Big Sky resort just an hour from town. There's some of the best fly fishing in the world, most notably in the Paradise Valley region down the road (on the way you’ll pass Livingston, an extra-cool small town and old Bourdain favorite). You’ve got hiking, biking, whitewater rafting, hunting, and anything else you can think of—plus hot springs, from the in-town Bozeman Hot Springs (where live bands rock the outdoor pools) to the world-famous and awesomely funky Chico Hot Springs nearby.
Must eat & drink: Eat and drink as heartily as possible at Open Range and Plonk before making your way to neon-signed dives like Crystal Bar and the local chapter of the Eagles Club, where it's not uncommon to see a live 13-piece jazz band playing to a crowd ranging from hipster poets to military vets. Montana Ale Works and Roost Fried Chicken are additional Bozeman musts, and you’ll definitely want to hit MAP Brewing to take in a pint overlooking the waters edge of the Bozeman Beach.
Don’t leave without: Taking a trip to Yellowstone. It’s only 90 minutes away. —Jay Gentile
Eau Claire, Wisconsin
For good brews and good tunes
“Wisconsin? The place with the cheese?” you might be thinking. And yes, it’s true! While it’s definitely appropriate to spend all your time here eating the two essential food groups—squeaky curds and deep-fried curds—the city of Eau Claire offers so much more. The homegrown music scene is the big draw, mostly thanks to Eaux Claires. The two-day music festival has drawn acts like Chance the Rapper, Erykah Badu, Sufjan Stevens, and more out to America's Dairyland. Although it’s taken a few years off due to Covid, it’s expected to come back in 2022. In the meantime, the Rock Fest and Country Jam are there to fill the void, as are the dozens of genre-spanning outdoor concerts and art gatherings that sweep the city year-round.
There’s also a helluva lotta beer to be sipped in Eau Claire. Leading the charge are Lazy Monk Brewing’s German beer hall and Chippewa River and Brewster Bros’ joint suds-and-spirits facilities. The most exciting of the bunch is arguably The Eau Claire Brewing Projekt, where the taproom is built inside the brewery so that you can see the very beer you’re drinking get made, canned, and zipped around on a forklift.
Must eat & drink: Hit up old classics like Stella Blues and Mona Lisa’s, and there are plenty of secret cheap eats you’ve got to ask a local to find—for example, the best flaky egg rolls in the Midwest at Egg Roll Plus and amazing hot beef sandwiches at dive bar Ray’s Place. Also, The Joynt on Water Street does $1 pints.
Don’t leave without: Enjoying an afternoon on the waterfront. The Chippewa River weaves throughout the city, and there are plenty of beaches where you can swim, ride a rope swing, lounge in a tube, or take a canoe out. —Dustin Nelson
The “other” Portland hasn’t let its newfound coolness go to its head
The East Coast’s Portland is rising in the ranks as a go-to for weekenders from cities like New York and Boston, not just for its historic character (think ivy-draped brick facades and cobblestone lanes) but because it’s cool. Like, really cool. The walkable downtown boasts dog-friendly breweries, boutique wineries, fancy donuts, industrial-chic restaurants, and food trucks that are outposts of those industrial-chic restaurants. Not only that, but the sweeping waterfront is peppered with sailboats ready to take you out to one of the hundreds of Calender Islands that scatter Casco Bay.
Must eat & drink: Duckfat. 100% go to Duckfat. You probably have even heard of Duckfat—it's one of the OGs of that whole chef-driven sandwich thing, and one of the best sandwich shops in the country. They cook everything in duck fat. The fries are legendary, and the main restaurant has a satellite operation that serves only the fried potatoes. For oysters, be sure to visit The Shop, a raw bar and shellfish market. Portland also has a ridiculous wealth of breweries. If you know your suds then you definitely know Allagash Brewing Company, but you may want to check out the boutique breweries like Rising Tide and Bunker Brewing.
Don’t leave without: Taking a sailing trip to one of the many Calendar Islands. Maine Sailing Adventures takes people out on a variety of sails; check out the day sail aboard the 74-foot British design gaff rigged cutter (if that means something to you, you belong in Portland). They also have a yoga sail (if you're into that), but more importantly they have a wine sail. For $65 you get to learn about (um, drink) wine on a boat with pairable snacks.—Meagan Drillinger
A nature-filled boomtown that never went bust
Tucked near the Oregon border in the foothills of Shasta County, it's easy to cruise past Redding, the coolest city between Sacramento and Portland—but doing so means you're missing out on the rugged California of yore. This is the gateway to some of the West’s best untapped natural wonderlands, among them the criminally underexplored Lassen Volcanic National Park and the lush waterways surrounding Shasta Lake. You need only point a vehicle—be it a motorcycle, RV, or bike—in any direction from Redding, and you're bound to get an idyllic swimming hole, roaring waterfall, or hot spring to yourself.
But Redding is more than just its wilderness. The town's most iconic landmark, Sundial Bridge, pulls quadruple duty as a pedestrian walkway over the Sacramento River, a luminescent art installation, a ginormous timekeeping device, and the site of a stellar Sunday farmers market. Stroll the ambling rows of shops in the Victorian house-lined downtown, then dip in for a pint at the region's oldest pub, Ale House, whose worn exterior and divey interior belie a formidable selection of craft taps and 100+ bottles.
Must eat & drink: Redding's not exactly a dining destination, but it's making some noise in the crowded world of California craft beer: A mini-crawl isn't complete without hitting Cedar Crest, Final Draft, and Woody's, each of which has great food.
Don't leave without: Located about 45 minutes north in Dunsmuir, Yaks will inspire curiosity with its nigh endless road signs. Give in. The 20+ burger options are the stuff of road-trip legend, and the place does unforgettable things with bacon, including a candied version made with chocolate porter. — Andy Kryza
Gulf Shores, Alabama
Soft white sands await in the South
Those who’ve never reveled in a mid-May weekend at the Hangout Music Festival might not even know that Alabama has beaches. But once you’ve experienced the soft, balmy magic of Gulf Shores, it’s hard to imagine anywhere along the Gulf Coast that’s closer to paradise. And while the annual music festival—which has drawn the likes of Outkast, Foo Fighters, and the Red Hot Chili Peppers—might be the beach town’s claim to fame, it’s far from the only reason to visit.
The Gulf Coast Zoo opened in a sparkling new facility in late 2019, including a primate island, a giraffe feeding experience, and Safari Club, a restaurant that can lay claim as one of the best in the state, however unexpected. Closer to shore, Gulf Shores boasts its own brewery at Big Beach, a popular work-and-play spot for the town’s growing mobile workforce. Gulf Shores borders Gulf State Park, where you can bike through some of the most stunning nature in Alabama and onto a beachfront snack shack in about half a day. If the place sounds enchanting, there’s even better news: It regularly rates among the most affordable beach towns in America, even as its popularity grows.
Must eat & drink: Being a pretty popular vacation spot, it’s easy to go out for dinner in Gulf Shores and accidentally wander into a tourist trap. Instead, head to Cosmo's for a A+ seafood dinner or The Keg for a cheeseburger that’ll send you home in a daze.
Don’t leave without: Stopping in for church service followed by a rager at the legendary Flora-Bama, just 20 minutes down the road. —Matt Meltzer
A laid-back, maple-infused lakeside getaway
While virtually a metropolis in one of America's most spread-out states, Burlington still has all the small-town vibes you expect from Vermont: outdoorsy style, beautiful brick lanes, and an ultra-chill way of life to go along with its eco-friendly approach to… well, everything. A hyper-local food itinerary should include simple crepes from The Skinny Pancake (skipping the pure maple syrup would be uncouth), pizza with maple-fennel pork sausage from American Flatbread, and maple creemee from almost anywhere.
Burn off all that maple with paddle boarding near Leddy Park and biking the beautiful lakefront path end-to-end; pursuing wares and fare from local culinary and visual artists at the 50,000 square-foot Soda Plant; visiting nearby Jeffersonville to ski Smugglers' Notch in winter; and—for the truly granola—playing Frisbee golf in the summer.
Must eat & drink: A can of Heady Topper at the The Farmhouse Tap & Grill: It's the legendary double IPA brewed in Stowe that launched the hazy/New England IPA craze, and still remains one of the most sought-after beers in America. Burlington itself is a considerable beer haven; be on the lookout for the vaunted Hill Farmstead, which rose from a college homebrew club to a world-renowned must-drink. A proper brewery crawl should run from Fiddlehead to Magic Hat to Switchback and end at Citizen Cider.
Don't leave without: Taking in an evening of charming debauchery on Church Street, the city's main vein of nightlife bridging the neighborhood dive bars of the old north end and the burgeoning arts district on the south end. The circuit will go something like: college bar, dive bar, college bar, Metronome dance party, Kountry Kart Deli. —Sean Cooley