The Coolest Small Cities in the U.S.

Where small town charm meets the perks of urban life.

It’s a tale as old as time: An ambitious kid grows up in a small town or cookie-cutter suburb, counting down the days until they’re old enough to move to the Big City™ and live out all their sitcom-fueled fantasies. Armed with a truck full of boxes and a lifetime’s worth of sheltered naivety, that kid lands in the nearest concrete jungle determined to make it no matter the cost.

Fast forward a handful of years, however, and living in a cramped apartment with three roommates, their rotating cast of paramours, and a single bathroom no longer seems so glamorous. Especially when the stock market takes a deep dive and inflation drives the cost of your daily bagel and coffee up to the high heavens. That’s exactly where America’s smallest but mightiest cities come in, appealing to all those ambitious kids who now dream of slower paces, cheaper rents, and cleaner air—without sacrificing the urban amenities they’ve come to enjoy.

Across the US, you’ll find dozens of 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. According to the Demographic Research Unit of the Department of Finance, to qualify as a “small city,” an incorporated area must have a population of 100,000 or less—all of which, we can only assume, will welcome you to town and swiftly point you to their favorite neighborhood dive bar.

Visit any one of these shining locales 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 far beyond antiquing—whether you’re just passing through or considering another big leap. Here are the 16 coolest small cities in America.

couple walking down the streets of bloomington, indiana
Visit Bloomington

Population: 79,968
A quintessential Midwestern college town imbued with enough indie grit to satisfy even the most discerning shoe-gazing hipster, Bloomington combines fairytale-level pastoral charm with all the perks of a larger city. Headlining live music acts in an intimate venue? Check. Unbeatable global cuisine? Double check. Celebrated breweries, wineries, and distilleries? Oh yes. Rugged hiking, biking, swimming, and fishing opportunities? You got it. All that plus dive bars aplenty, top-quality sporting events, thoughtful art galleries, farm-to-table eats around every picturesque corner, and rents so cheap they make nearby Chicago look like Dubai.

Must eat & drink: Upland Brewery and its handful of local off-shoots is a rite of passage for any B-towner, as is grabbing pints at the Bishop or shooting a round of pool at the Vid. Pillowy momos beckon from Himalayan mainstay Anyetsang's Little Tibet Restaurant, while FARMbloomington has cheffy New American creations on lock. Finish your night like a true college kid with a slice from Mother’s Bear Pizza.

Don’t leave without: Catching the Little 500, a premiere town-gown cycling event that draws upwards of 25,000 cheering fans every April. If you haven’t seen Breaking Away, the 1979 blockbuster charmer showcasing the student-centric event, get on that. —Meredith Heil

university of california merced building
UC Merced

Population: 89,308
Imagine you wanted to visit Yosemite, but along the way, you get a chance to live out your retro road trip dreams. Enter Merced, a town just an hour from the national park, with a selection of vintage eras to choose from, spanning old western saloon vibes, 1920s art deco architecture, 1950s neon signs, vinyl or cassette tape shops, and a theater suitable for Back to the Future screenings. Everything here is in with the old and in with the new, since modern remodeling awaits on the insides.

Dig for treasures in the Merced Antique Mall or at Second Time Around. If you’re into old machines, check out the Grapes of Wrath-style farming equipment and old railway machinery at the town’s Agriculture Museum. Or head to the Castle Air Museum in nearby Atwater for retro aircraft. All you’ll be missing at that point is your DeLorean.

Must eat & drink: Merced’s central-California location means you’ll have all your Napa and Sonoma wines in easy reach at Hi-Fi Wine or Vinhos, but kick things up a notch by visiting Vista Ranch, where you can see (and taste!) the magic as it's happening. Chase it down with cocktails from Native Son and craft beer from 17th Street Public House. Get high-end, seasonal farmers produce turned into clever dishes at Rainbird, or go for traditional Mexican cuisine with vegetarian options at J&R Tacos.

Don’t leave without: Lighting up fresh buds grown right in the valley. In fact, there’s even a convent of nuns in Merced who grow their own cannabis, and are you really gonna pass up a chance to ask a sister to pass the bowl? —Danielle Hallock

aerial view of juneau, alaska
Photo courtesy of Visit Juneau

Population: 31,973
Alaska’s capital city is the embodiment of the great frontier, where you can get your nature fix by scaling broad glaciers, watching whales frolic in the teal blue waters, following overgrown trails up to breathtaking summit views, and kayaking to your heart’s content, all before settling in for a hearty meal of wild-caught shellfish at a top-notch restaurant. And don’t forget the beer—home to Alaskan Brewing Company, Juneau takes its suds very seriously.

Fortify yourself against the sharp winter winds (or blinding summer sunlight) with a sturdy Smoked Porter, then get to know the downtown scene by way of South Franklin Street’s historic lineup of original saloons and Victorian-era architecture. The 1898 Gold Rush town’s backdrop could easily double as the set of any dusty Western film, in the best way possible. Or venture out to Heritage Square, where various forms of Southeast Alaskan indigeneous art are on display at Sealaska Heritage Institute and beyond.

Must eat & drink: Booze-wise, Alaskan Brewing Company is the obvious no-brainer here, followed by stops into Devils’ Club Brewing Company and Amalga Distillery—or The Narrows for a quality cocktail. Hungry? Snag a table at local favorites like The Rookery, In Bocca Al Lupo, Salt, and the stately Alaskan Hotel & Bar, which dates back to 1913. Last but not least, the Red Dog Saloon is the place where you’ll want to post up for that iconic John Wayne-style photo-op.

Don’t leave without: Sure, it’s a touch corny, but if you go all the way to Juneau and don’t try your hand at panning for gold in Gold Creek, you’ll absolutely regret it. —Meredith Heil

fort myers beach
Photo by Jason Boeckman, courtesy of Visit Fort Myers

Population: 92,245
Forget Miami. Smell ya later, Tampa. It’s all about fun in the sun in Fort Myers, one of Florida’s most underrated beachfront escapes. This laid-back small city makes good use of its positioning on the state’s western edge, with easy access to a number of idyllic islands as well as inland draws like wildlife preserves, outdoor recreational areas, and, perhaps most famously, a network of world-class baseball stadiums and practice facilities that spring to life each March during MLB’s Spring Training. Sports fans descend upon the city for the annual event, infusing Fort Myers with an infectiously enthusiastic spirit while catching the Bigs in action for a fraction of the cost of regular season admission.

But that’s not to say it's all peanuts and CrackerJack down here—Fort Myers is also rife with excellent places to eat and drink, from sandy seafood shacks and buzzy breweries to white tablecloth emporiums. And don’t forget about the beaches: miles of soft sand giving way to warm, crashing waves, bordered by a bounty of secluded pockets to lounge the day away.

Must eat & drink: The Lighthouse Restaurant serves up the classics alongside sweeping waterfront views, while local institution Matanzas Harborside Restaurant ups the class factor without venturing into stuffiness. The Tubby Pig Brew Pub merges housemade brews with one-of-a-kind American Thai fusion dishes, Smoke'n Pit Bar B Que caters to the carnivorous crowd just north of downtown, and Heavenly Biscuit on Fort Myers Beach is, well, the name says it all.

To drink, beer fans make a beeline to Fort Myers Brewing Company (which, incidentally, also pours an excellent original hard seltzer), Crazy Dingo Brewing Co. marches to the beat of its own sudsy drum, and Millennial Brewing Company leans into its eponymous generation’s tech-savvy vibes.

Don’t leave without: Taking an afternoon excursion to nearby Sanibel Island, where you can rent bikes and cruise the shoreline in search of tasty frozen cocktails, captivating bird-watching, and the ultimate summer tan. —Meredith Heil

firefighters walking a parade in hot springs, arkansas
Visit Hot Springs

Population: 38,114
As to be expected with a city named Hot Springs, it first developed thanks to the boiling geothermal water flowing beneath its surface. Mobsters like Al Capone and Owen “The Killer” Madden flocked to the soothing substance for their preferred vacations (also the gambling); baseball players like Babe Ruth used them to relax after spring training. They’re the reason part of the city is now enveloped by technically the nation’s first national park—with miles of gorgeous mountain trails to explore.

Years later, a historic bathhouse row remains the main attraction, and a few are still in operation. Superior Bathhouse Brewery whips up tasty brews utilizing the hot springs. There’s a hotel, a spa museum (kept exactly as it was when it was in operation) and tourist shops. Two bathhouses, Buckstaff and Quapaw, still operate; only Buckstaff still utilizes the geothermal water. Every year there’s a “world championship” running of the tubs race (which is pretty much exactly what it sounds like). For more history, the Gangster Museum of America and the Josephine Tussaud Wax Museum tell quirky tales. The wax museum even gets immersive: as the former Southern Club casino, at the end of the tour you’re privy to the escape tunnel used by patrons when it was raided. On the other side sits the storied Arlington Hotel.

Then, take advantage of the Natural State. Beyond the national park, nearby Lake Catherine and Lake Ouachita State Parks offer hiking, waterfalls, houseboating, and all the usual water sport suspects. The 210-acre Garvan Woodland Gardens throws an annual tulip festival extravaganza. And the area’s unique topography makes it an unusually fertile place to dig for gems—including diamonds. Try your luck at Crater of Diamonds State Park; as of the beginning of May, 260 diamonds had already been found this year.

Must eat & drink: It’s the only place you can have beer made with geothermal waters, so a stop at Superior Bathhouse Brewery is mandatory. There are 18 rotating styles on tap to try in a four-ounce sample, a flight of four, or a Beer Bath of all 18 ($35). Pair it with a burger and top off with a root beer float, also made with the hot springs.

Don't leave without: You’re in town, you gotta try the water. If a stop at Superior or Buckstaff isn’t in the cards, bring an empty jug to fill up at one of the water fountains around town. There’s a reason people thought they had healing powers. —Vanita Salisbury

boardwalk leading to ferris wheel in myrtle beach, south caroline
Visit Myrtle Beach, South Carolina

Population: 37,100
So much more than the Myrtle Beach of your debaucherous high school senior trip memories, this South Carolina vacation hub has been keeping visitors of all ages on their toes since 1936, when the final stretch of the 2,700 mile-long Intracoastal Waterway linked to Horry County. Today the coastal playground attracts thousands of visitors, thanks to its blend of flashy attractions, diverse bars and restaurants, pro golf courses, jaw-dropping natural areas, and, of course, 60 full miles of shoreline bliss.

Vegas-style shows top the bill at the area’s many performance venues, while outdoorsy types can’t get enough of the jet ski-ready surf, and everyone’s inner child can’t help but marvel at centrally located Family Kingdom’s iconic SkyWheel, one of the tallest Ferris wheels in America. Aquatically inclined? Pop over to Ripley’s Aquarium for 85,000-square-feet of underwater sights, or face your fears with a scaly animal encounter over at Alligator Adventure. There’s no shortage of live music venues, beach bars, dance clubs, and the like to keep night owls happy—just be sure not to miss that early morning tee time at one of the 100+ manicured courses. And considering it’s one of the fastest growing small cities in the country thanks to a recent uptick in international business investment, Myrtle Beach’s future looks brighter than the SkyWheel on a pitch-black night.

Must eat & drink: Overstuffed tacos from Nacho Hippo, La Poblanita Restaurant, or Banditos Cantina are an instant crowd-pleaser. Retro boardwalk fixture Peaches Corner grills up the best foot-long hot dogs in town with vibes to match. And Duck Donuts, Hoskins, and Olympic Flame Pancake House cover all your breakfast bases. For barbecue—this is South Carolina, after all—pop over to Little Pigs Bar-B-Q for some hickory-smoked pork butts laced with a tangy mustard sauce. And for ocean-fresh seafood in varying atmospheres, it’s all about sustainability focused Hook & Barrel, Fire and Smoke, Sea Captain's House, Wicked Tuna, and the hokey yet always-packed Captain Benjamin's Calabash Seafood Buffet.

Don’t leave without: Sampling the wares at Palmetto Distillery, South Carolina’s first-ever legal moonshine distillery known for their award-winning White Lighting and ready-to-drink cocktails, before getting schooled in the Shag, SC’s official state dance, with a free lesson over at Fat Harold’s. —Meredith Heil

winding road leading to the ocean in kahului, hawaii
Tim Roberts Photography/Shutterstock

Population: 29,993
Boasting a super well-connected airport, a comparative dearth of tourist traps, and an up-and-coming dining scene to rival its firmly established surf scene, Maui’s largest city offers a welcome respite from more overrun island destinations. The population hovers around 30,000 at any given time, representing a healthy mix of mainland expats and local lifers raking in a household income that falls within the top 10 for small American cities. Bars and restaurants run the gamut here, as do other attractions like shopping districts, art, and cultural museums, but let’s get real—this is Hawaii, and you’re here to hit the beach.

Surfers of every skill level can be found splashing among Kahului’s inviting waves, while casual beach-goers admire their efforts from their posts on the soft sand. Windsurfing, parasailing, and kitesurfing are commonplace at Baldwin, Kanaha, and Ho’okipa Beach Parks. Further inland, verdant natural escapes like Kanaha Pond State Wildlife Sanctuary (with its plethora of colorful birdlife), Iao Valley State Park, and Maui Nui Botanical Gardens offer the turf crowd plenty to see and do.

Must eat & drink: From celebrity chef-helmed restaurants to sandy roadside stands, there’s no going hungry here. Food trucks abound, with standout options including Geste Shrimp Truck, Maui Fresh Streatery, Sumo Dogs Maui, and Plate Lunch Market’s Thai Me Up, Ono Teppanyaki & Seafood, Like Poke, Tacos Maui 8 Wonder, MoOno Acai Bowl, and Kalei’s Lunch Box. Elsewhere, Top Chef vet Sheldon Simeon packs a punch at Tin Roof, fancy fare dominates Bistro Casanova, Poi by the Pound peddles the best bang-for-you-buck Hawaiian eats, buzzy Wow-Wee Maui’s Kava Bar & Grill whips up the best Loco Moco in town, and nothing hits the spot on a sunny day better than a pineapple sherbet from Tasaka Guri-Guri.

Don't leave without: Cruising Hana Highway, a 64.4-mile stretch that winds dramatically around Maui’s eastern coast, passing through dense tropical rainforests, quiet shorelines, majestic waterfalls, and a whopping 59 richly historic bridges. —Meredith Heil

waterfall in ithaca, new york
Visit Ithaca

Population: 31,710
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 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. Do go chasing 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 miss Finger Lakes Distilling, where you trace a spirit’s journey from still to barrel to cocktail all in one breathtaking setting.

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

telescope pointing at a starry sky in flagstaff, arizona
Discover Flagstaff

Population: 76,989
If you’re ready to unpack your preconceptions about Arizona—namely, that it’s a barren expanse of lonely cacti, dusty highways, and bronzed snowbirds—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. Trekking highlights include 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 temperatures dip, hit the slopes at the Arizona Snowbowl, where we’re sure you’ll be more than satisfied with 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. In other news, Flagstaff is Arizona’s craft beer hub, with standout joints like Mother Road, Historic Brewing, and Proper Meats + Provisions holding it down.

Don’t leave without: Stargazing at the Lowell Observatory. This is the world’s first International Dark Sky City, after all. —Lauren Topor Reichert

aerial view of deschutes river in bend, oregon
Visit Bend Oregon

Separated from 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—serenely bisected by the mighty Deschutes River—manages to give off immaculate small-town warmth despite the fact that the city’s sprawl has recently pushed its population to just over 100k. It’s an ever-growing mix of cowpokes and creatives, college kids and career bartenders, free-spirited artisans and hardy agrarians, all here to breathe in the scenery and take advantage of 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 the multi-award-winning 10 Barrel, 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 succulent 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

aerial view of greenville, south carolina
VisitGreenville SC

Population: 72,095
You might assume South Carolina’s best small city would be found along the coast, but head inland and you’ll find the true shining star. Just under two hours down the road from Asheville, NC, 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, or Fall for Greenville. The neighborhood of West Greenville is an arts hub in and of itself, and throughout the city, you’ll find more than 95 public works of art, including glass-master Dale Chihuly’s striking Rose Crystal Tower.

Must eat & drink: The walkable, bikeable 22-mile Swamp Rabbit Trail is lined with good eats, including Soby’s or, further out, Swamp Rabbit Café & Grocery. There’s also Gather, a food hall fashioned out of repurposed shipping containers and stocked with indulgent goodies from all across the country, including fried chicken and donuts, Miami-style 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

live band performing at bozeman hot springs
Bozeman Hot Springs

Population: 54,539
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: Feast 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, for crying out loud. —Jay Gentile

eau claire river, wisconsin
Visit Eau Claire, WI

Population: 69,441
You might be thinking, “Wisconsin? That place with all the cheese?” And yes, it’s true. Yet while it’s 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, a long-running two-day music festival that has drawn acts like Chance the Rapper, Erykah Badu, Sufjan Stevens, and more out to America's Dairyland. And while that particular fest's days seem to have come to an end, the Rock Fest and Country Jam are there to fill the void, as are the dozens of genre-spanning outdoor concerts and arts gatherings that sweep the city year-round.

There’s also a helluva lotta beer in these parts. Leading the charge are Lazy Monk Brewing’s German beer hall and Chippewa River and Brewster Bros’ dual suds-and-spirits facilities. The most exciting of the bunch is arguably The Eau Claire Brewing Projekt, where the taproom lurks inside the brewery, so you can watch the very beer you’re drinking get fermented, canned, and zipped around on a forklift.

Must eat & drink: Hit up old classics like Stella Blues and Mona Lisa’s, plus plenty of secret cheap eats you’ve got to ask a local to find. For example, the best flaky egg rolls in the Midwest hail from Egg Roll Plus, while dive bar Ray’s Place hawks the most amazing hot beef sandwiches.

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 set sail in a canoe. —Dustin Nelson

boats docked at a harbor in portland, maine
Photo by Serena Folding, courtesy of Visit Portland

Population: 68,313
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 just so damn cool. Like, really, really cool. The walkable downtown boasts dog-friendly breweries, boutique wineries, fancy donuts, industrial-chic restaurants, and food trucks that serve as 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 scattered about scenic 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 (duh). The fries are legendary, and the main restaurant operates 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 assuredly know Allagash Brewing Company, but you may want to check out boutique options like Rising Tide and Bunker Brewing while you’re at it.

Don’t leave without: Cruising out to one of the many Calendar Islands. Maine Sailing Adventures takes people out on a variety of rides; check out the day sail aboard the 74-foot British design gaff rigged cutter (if that means something to you, you belong in Portland). More importantly, they offer a wine sail, where you get to learn about (er, drink) wine on the water complete with pairable snacks.—Meagan Drillinger

friends enjoying hangout music festival in gulf shores, alabama
Hangout Music Festival

Population: 15,736
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 lays claim to being one of the best in the state, however unexpected. Closer to the sand, 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: Considering it’s a pretty popular vacation spot, it’s easy to go out for dinner in Gulf Shores and accidentally wander into a tourist trap. Avoid the commoners by heading to Cosmo's for an ace 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

burlington parks waterfront
Burlington Parks, Recreation & Waterfront

Population: 44,781
It might be a relative metropolis compared to its fellow Green Mountain hamlets, but Burlington maintains 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—pronounced sur-up—would be uncouth), pizza dotted with maple-fennel pork sausage from American Flatbread, and a Vermont Maple Creemee from any roadside stand.

Burn off all that maple sugar with paddle boarding near Leddy Park or 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 is always a good time, while visiting nearby Jeffersonville to ski Smugglers' Notch is a wintery must. And—for the truly granola—there’s always a few rounds of Frisbee golf in the summer.

Must eat & drink: Suck down a coveted 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 much-revered Hill Farmstead, which rose from a college homebrew club to a world-renowned beer nerd white whale. A proper brewery crawl should run from Fiddlehead to Magic Hat to Switchback, before culminating at Citizen Cider.

Don't leave without: Taking in an evening of charming debauchery on Church Street, the city's main drag that bridges the neighborhood dive bars of the old north end with the burgeoning arts district on the south end. The circuit will go something like: college bar, dive bar, college bar, dance party at Club Metronome, Kountry Kart Deli. —Sean Cooley

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