The 25 coolest towns in America: 2018
Big, sexy cities get a lot of the hype in the world of American travel. Millions of people and easily accessible airports will do that. But as cities become prohibitively expensive and vacations get shorter, smaller towns have become appealing options. Talented chefs and creative entrepreneurs are going where the cost of doing business is cheaper, and what results are towns across America where the food, drinks, and general good times are often better than in major metropolitan areas. And, in many cases, these towns have way better access to nature than the big cities.
We took a look at towns with populations under 100,000 in this great land of ours, from a California beach town with some of the best surfing in the world to a tiny farm town in the Hudson Valley with an epic food and drink scene. From the plains of Kansas to the mountains of New Mexico and even out to the Hawaiian islands, we’ve found the ultimate collection of towns where people can have the weekend of their lives — and maybe even stay for good. Throughout these 25 selections (in no particular order), you’ll find some of the coolest places in America that don’t get nearly the attention they deserve, and get inspired for your next under-the-radar getaway.
1. Greenville, South Carolina
No small city in America punches above its culinary weight quite like Greenville, a city of just over 67,000 with restaurants better than cities ten times its size. In a 10-block radius near its downtown, you can find over 120 locally-owned spots. You can stroll down Main Street to one of the best burger joints in America at Grill Marks, head across the Reedy River to the James Beard-nominated The Anchorage, or cool off with a drink on the best rooftop bar in South Carolina at Up on the Roof.
But it’s not all calorie consumption in this underrated hotbed of Southern cuisine. Calorie burning is equally enjoyable along the Swamp Rabbit trail, a calm, woodsy recreational trail perfect for biking down to the town of Travelers Rest. To get further into nature, drive a short ways to Caesar’s Head State Park where a four-mile trail takes you to the spectacular Ravens Cliff Falls, where changing colors make for perfect fall photo-ops.
2. Bozeman, Montana
Bozeman sits in a nearly 5,000-foot-high plateau surrounded by stunning mountain ranges and, frankly, some of the most beautiful landscapes in the country. An hour and half drive takes you to Yellowstone National Park, Big Sky Ski Resort is only an hour away, and smaller ski resorts are reachable in 30 minutes. Bozeman is also heaven for fly-fishing fans, who can cast at Gallatin, Madison River, or Yellowstone River. Horseback riding is also big in Bozeman, as are rodeos (a big one each summer is the Bozeman Stampede). Add in hiking and mountain biking, and there’s no shortage of outdoor activities.
Bozeman is also home to Montana State University, which gives it a cool college town vibe – including brewpubs and museums. The Museum of the Rockies actually has the country’s largest collection of dinosaur bones. A crop of new restaurants have recently opened in Bozeman, adding to the great selection of affordable taco spots, Korean barbecue, and other college town fare. Despite the cold weather — December through March can be brutal — Bozeman’s charms have made it one of the fastest growing towns in the region.
3. Flagstaff, Arizona
Flagstaff looks absolutely nothing like the Segoura-cactus-and-active-senior-community Arizona of your mind’s eye. Instead, it’s a woodsy mountain town that’s more akin to Colorado or northern Idaho, full of artists, students, and a smattering of hippies that keep it forever interesting.
The snow-capped mountains loom in downtown Flagstaff’s background, where you can walk to half a dozen breweries like Beaver Street Brewing and Lumberyard before getting the best traditional barbecue in the state at Bigfoot BBQ — then treating yourself to something sweet from Brookside Chocolate Company.
As the outdoorsy jumping-off point to all the spectacular nature of the high desert, Sedona is only 30 miles south, and the Grand Canyon is less than an hour away. Coolest yet, Flagstaff is also home to the Lowell Observatory, one of the oldest observatories in America and one of the best spots in the country to observe stars in the desert.
4. Gardiner, New York
A few years ago, you’d hardly be able to call Gardiner cool. It was little more than a farming town in the Hudson Valley, and its only visitors were families camping at Yogi Bear’s Jellystone Park. Thankfully, a man named Ralph Erenzo unwittingly changed all that. In the early 2000s, Erenzo had a simple dream to buy land and open up a camping hostel for rock climbers. But he was met with protests and insurmountable red tape from people who didn’t want outdoorsy vagabonds in their backyard. But they couldn’t stop him from pursuing agriculture — which, technically, includes booze. Erenzo went on to fight against New York’s outdated Prohibition laws to create the first distillery in the state since the ‘20s, Tuthilltown Spirits.
You can visit the Tuthilltown Spirits farm to tour the distillery, barrel barn, bottling facility, and gristmill. Sample a flight of its famed whiskey, including the award-winning Hudson Baby Bourbon, or try other spirits that range from vodka distilled from apples to fruity liqueurs made from local produce. But Tuthilltown isn’t the only reason worth coming to Gardiner. In town, visit Gardiner Liquid Mercantile, which produces its own spirits and whips them into craft cocktails, from a perfectly-made old fashioned to a whimsy s’mores-inspired White Russian. If you’re a little more health-minded, Gardiner also has an epic farmer’s market, farm-to-table restaurants, nearby upstate New York Airbnbs, and plenty of hiking and rock climbing opportunities in the Shawangunks.
5. Lauderdale-By-The-Sea, Florida
If someone dropped you on the sand in this little beach town, you wouldn’t believe you were smack in the middle of one of the biggest metro areas in the country. But by bucking the Florida trend and banning high-rise condos, this village between Ft. Lauderdale and Pompano Beach has created an identity of its own. Stroll on the sand in front of Aruba, the landmark beach cafe with destination-worthy Bimini bread, and you’ll feel almost like you’re on a remote Caribbean island with nothing but a concert bandshell and beach bar behind you. The hotels are the charming, beachfront two-story spots of family vacation nostalgia, and remind us that while Florida has grown, it still knows its funky coastal roots.
For divers, there is simply no better place in South Florida outside the Keys, where you can access an underwater shipwreck park from nearby Hillsborough Inlet. The SS Copenhagen — the odd wreck on the National Register of Historic Places — sits in only 30 feet of water, meaning novice divers and snorkelers can examine its remains on the reef. You can also find friendly nurse sharks, tropical fish, and stingrays along the coast. And in densely-packed South Florida, a town this relaxing and empty is a true find.
6. Ashland, Oregon
If Elizabethan England were populated by all the people who went to Woodstock — 50 years later — you’d find something like present-day Ashland. The city famous for its Shakespeare festival is decked out in buildings with architecture designed to look like the English countryside 500 years ago. But it’s actually filled with hippies hanging on to the glory days of the ‘60s and ‘70s with all the legal marijuana they can. It’s a place where you’ll meet far-out seniors, and won’t find it the least bit odd to have a long conversation about LSD with a guy in his 70s over a craft beer at Caldera Brewing.
Caldera is one of many Ashland breweries, but if you want to try a few in one spot head to Liquid Assets, which, in addition to having a killer draft selection, boasts over 250 wines by the bottle. If you’d rather be outdoors, grab a kayak and head down the tree-lined Rogue River. You can also trek through the Oredson-Todd woods, home to Oregon’s only native orchid and one of the most underrated waterfalls in the west.
7. Lawrence, KS
Kansas isn’t high up on many traveler’s bucket lists (barring those that are a little too obsessed with The Wizard of Oz), but this mini city is keen on changing everyone’s minds about the state. Home to the University of Kansas, Lawrence is full of youthful energy — especially when it’s basketball season when things can get a little wild at the many sports bars with dirt cheap drink deals.
The historic Massachusetts Street’s facade is a slice of traditional Midwestern America, but the restaurants and bars are anything but old school. Free State Brewing Company has an excellent selection of craft beers, Merchants Pub and Plate’s diverse gastropub menu will satisfy even the pickiest of eaters in your group, and Bon Bon! offers up a unique take on comfort snacks with menu items like Thai-style wings and hot chicken steamed buns. A little-known fact about Kansas: they’re really into cinnamon rolls, and they know how to make them really well. Try Lawrence’s best at WheatFields Bakery Cafe on Vermont Street.
To work off that cinnamon bun weight, head to Prairie Park Nature Center — which features prairie, woodlands, and wetlands — or go further afield to Clinton Lake for hiking and biking trails, as well as excellent freshwater fishing.
8. Taos, New Mexico
For locals, the quirks of living at an altitude of nearly 7,000 feet is a minor trade-off for the joys that their high desert home brings. Taos is a thriving artist community with excellent art museums, including the Harwood Museum of Art, and dozens of galleries and studios that are spread around the town’s sienna-hued adobe structures.
Taos’ artists take inspiration from a landscape of ochre sands filled with sagebrush, with the snow-capped peaks of the Sangre de Cristo Mountains in the background. The mountains turn red in the evening light, hence their name, which translates to “blood of Christ.” The Rio Pueblo de Taos runs alongside the town, which is dotted with willow trees.
In the winter, Taos can be dusted with snow, and the excellent Taos Ski Valley resort is a mere 30-minute drive away (check out the best Taos ski hotels for your trip). But winter temperatures rarely plunge too low; sunny, warm days are the norm most of the year in this arid environment — which means plenty of days to enjoy alfresco patio dining and outdoor music festivals, including the Music in the Park series.
Orange Beach, AL
9. Orange Beach, Alabama
Just west of Florida, you’ll find one of the coolest beach towns in America in Orange Beach, beginning with the sprawling Gulf State Park and finishing with the best Stateline roadhouse in the land. Orange Beach has done a lot to elevate itself from its Redneck Riviera past. It began with opening the Wharf entertainment district, complete with a giant Ferris wheel and the World Food Championships every November. It has also added great restaurants like Anchor Bar & Grill and Big Fish to bring New Orleans-worthy food to this little shore town.
Of course, the reason people come here is for the beach, and unlike a lot of Gulf Coast beach towns, Orange Beach has a huge stretch completely devoid of condos. Along its eight miles of white sandy shoreline, you’ll find Gulf State Park, with plenty of bike trails that’ll take you from the coast into the swamp and back out again. This November, it’ll open its first park lodge, complete with cool stuff like webbed windows so birds can peek in without flying through.
Just down the road, you’ll find Gulf Shores, home of the Hangout Music Festival and the new Big Beach Brewing. Turn the other way and you’ll find the Flora-Bama, a bar on the Florida-Alabama Stateline famous for its annual mullet toss where patrons throw fish from state to state.
New Hope, PA
10. New Hope, Pennsylvania
There are very few places on earth where you’ll find biker gangs sharing the same bar as a bunch of drag queens. But that’s exactly the two main communities you’ll find in this tiny Bucks County town — where motorcycles are parked all the way down Main Street underneath pride flags. New Hope’s biggest draw for families may be the scenic train station and the famous Bucks County Playhouse, but the most fun way to spend the day is hopping between the dozens of quirky shops. Browse funky costumes at Night Bird Vintage Clothing, punk rock clothes at God Save the Qweens, and witchy relics straight out of The Craft at The Creeper Gallery. Be sure to end the day with an ice cream cone at Moo Hope.
There are plenty of festivals held throughout the year in New Hope (and in Lambertville on the New Jersey side of the river, just over the walkable suspension bridge). But you should make a point of visiting in October for the iconic, annual High Heel Drag Race, where participants wearing high heels will carry a pumpkin downtown, decorate it, and return to cross the finish line before hitting the bar.
San Marcos, TX
11. San Marcos, Texas
Over the last decade or so, a lot of Austin’s hippie charm has been replaced by hipsters and tech-talk. So the mantle of quirky, outdoorsy college town has been taken over by San Marcos, about 30 miles south and home to all that was great about Austin 30 years ago. Here, a guy named Sun God dances in front of the courthouse on Mondays, and musicians who can’t afford Austin play spots like the Cheatham Street Warehouse and Stonewall Warehouse almost every night. Those venues reside in the Square, San Marcos’s four-sided playland of live music and cheap bars where college kids and returning veterans listen to everything from reggae to rock to blues and spend a fraction of what they might have in larger locales.
Summer is the prime time to visit, when floating in tubes down the San Marcos River under shady trees through crystal-clear waters is the pastime of choice. You’ll find students, families, and young professionals floating all day while toting cases of beer and basking in the Texas sun.
The food here is fantastic, as well, with Austin staples like Blue Dahlia opening San Marcos outposts (with a lot less waiting). You can also drive out to Lockhart and eat at legendary barbecue joints like Smitty’s Market, Kreuz, and Black’s.
12. Durango, Colorado
Durango lies just north of the New Mexico border, tucked into a valley of the Rocky Mountains. The 19th-century mining town is now home to Fort Lewis College and lucky residents who can wake up on a wintry Saturday and decide whether to ski at one of the half-dozen nearby ski areas or the larger Purgatory Resort, just a half-hour drive away. Add summer hiking in the two-million-acre San Juan National Forest, kayaking or rafting on the Animas River, fishing, hunting, and mountain biking, and pretty soon you’re out of breath.
Besides sitting in the middle of a stunning natural playground, Durango has five brewpubs and enough restaurants to offer you tasty ways to refuel after a day in the mountains. Given that it’s a college town, you’ll find plenty of pool tables to lose a few quarters at after dinner, as well. While locals love their town’s outdoor options and friendly vibe, a big draw for visitors is the Durango Silverton Railroad. It’s a historic train that takes three-and-a-half hours to get north to Silvertown, following the Animas River along a surprisingly narrow track cut into the mountainside.
Paso Robles, CA
13. Paso Robles, California
In stark contrast to the sometimes-stuffy, Instagram-filtered vibe of Napa, this quirky little town on the Central Coast is everything one looks for in a California wine country getaway. It’s home to dozens of wineries, which not only serve delicious wine without pretension but also have other attractions like a $15 cheese pairing at Le Vigne or backyard games and cornhole at Chronic Cellars. Downtown, you can sober up by scarfing a massive cinnamon bun at Joe’s Place or going farm-to-table crazy at Thomas Hill Organics.
A short drive and you’re at the Pacific Ocean, where you can either jump in the water and catch a wave at Cayucos Pier or just stand with a cold beer and watch the surfers. If you’re looking to get a little more active, cruise up the Pacific Coast Highway to Fiscalini Ranch Reserve, where a cliffside trail takes you past some of the most spectacular views in the state.
14. Annapolis, Maryland
We can’t quite put our finger on why, but Washington, DC, is feeling a bit tense lately. If the idea of taking a tour of the Capitol Building has you breaking out in a cold sweat, it’s time to turn your attention to the other nearby towns in the mid-Atlantic area, like beautiful, blood-pressure-lowering Annapolis. Less than an hour away from DC, the town on the Chesapeake Bay is one of the country’s best sailing capitals. Learn to sail at the Annapolis Sailing school, rent a schooner and cruise around town if you already know what you’re doing, or leave it to the pros and go on one of the many sailboat booze-cruises offered at sunset. There are also tons of yacht races and boat shows if you prefer to just ogle at the vessels from the safety of land.
Those in need of a drink or five will want to visit Great Frogs Winery or the Chesapeake Brewing Co. And much like Baltimore, Annapolis loves its crab, with plenty of waterfront seafood restaurants dotted throughout town like O’Learys Seafood, Boatyard Bar & Grill, and Carrol’s Creek Cafe.
15. Boone, North Carolina
Cruising past the stunning fall foliage of the Blue Ridge Parkway, it’s easy to miss little Boone, nestled in the mountains of North Carolina. But a stop in this earthy, outdoorsy college town is totally worth it, where it seems a little chunk of Oregon got dropped in Western Carolina. The charming main street slopes gently uphill towards the mountains, lined with independent eateries like Carolina Pizza, Boone Bagelry, and one of the coolest sandwich shops in the country at Our Daily Bread. Students from Appalachian State University fill most of the stores, giving Boone a young, carefree energy almost everywhere.
Outside of town, it’s all about the outdoors. The Blowing Rock is the most famous attraction, an epic rock formation with panoramic views out over the Johns River Gorge. There’s also hiking through the bright colors under the Blue Ridge Parkway or trekking up to Grandfather Mountain and standing atop a rock at sunset. The mountain also has a mile-high swinging bridge between its peaks, which doesn’t swing so much as it suspends over a steep canyon. Pro tip: Look out instead of down.
La Crosse, WI
16. La Crosse, Wisconsin
Western Wisconsin has a noticeably different feel than the rest of the state, a little less Midwest country and a little more river-coastal. Nowhere is this more obvious than in La Crosse, known nationally as the home of Old Style beer and regionally as one of the top downhill skiing destinations in the region. Mt. La Crosse offers 18 runs with pretty respectable slopes, and you’ll find gorgeous hiking, winter mountain biking, and snowshoe trails at Upper and Lower Hixon Park. La Crosse has a huge biking community, as well, with the annual La Crosse Bicycle Festival drawing thousands to the city. To bike like a local, head out to the La Crosse River State Trail or jump on one of the monthly Beer By Bike Brigade rides that takes you through many of the city’s best beer bars.
The nightlife here takes on a distinctly western feel, too, with breweries like Pearl Street and Turtle Stack complimenting intimate live music at Bodega Brew Pub and Root Note. But the best bar in town is Casino Bar, where the bright lights outside promise “lousy service,” and the bartenders aren’t afraid to pour heavy. If you’d like something a little classier, the Charmant Hotel plates modern French food on an outdoor patio with views out over the city. And make sure you don’t leave town without getting some candy and a chocolate-dipped waffle cone at Pearl Street Ice Cream.
17. Newburyport, Massachusetts
Outside of Boston, most people think of Massachusetts as being filled with rich vacationers with shore homes and boats named after their grandmothers. But Newburyport, 30 miles north of Boston, offers all the things those wasps love about Massachusetts — gorgeous coastline, decadent seafood, mind-blowing sunsets — just without the wasps.
This old seaport town may have plenty of history and old buildings to prove its age, but it’s also home to live-music venues featuring local bands, breweries, and a vibrant restaurant scene that sells more than just lobster. Start the day at Mad Martha’s Island Cafe, a laid-back beach eatery, and order the Crabby Patty (crab, egg, and cheese with horseradish sauce) or the caramelized-banana French toast. Then go to the Parker River Wildlife Refuge, which has miles of beach, marsh, dunes, cranberry bogs, and forest ripe for exploring. Here, you can do everything from biking to kayaking, as well as some of the best bird watching in the Northeast. Back in town, fill up at Thai restaurant Brown Sugar by the Sea (a sister restaurant to the acclaimed Brown Sugar Cafe in Boston) before having a refreshing craft cocktail at The Paddle Inn and watching the sunset over the ocean.
Port Townsend, WA
18. Port Townsend, Washington
A onetime northwest maritime hub that’s preserved the relics of its boomtown past, Port Townsend captures the feel of the Northwest over 100 years ago without turning into a full-on theme town. The classic brick structures along downtown Water St. date back to the turn of the last century, filled with craft shops like Bazaar Girls Yarn Shop and Conservatory Coastal Home. A rigorous afternoon of shopping is best shaken off with a waterfront local beer at Sirens Pub on the Water or one of the town’s several microbreweries.
Meandering through uptown is a lesson in Victorian architecture, with grand old homes that once belonged to shipping and logging magnates filling the streets. You’ll see even more impressive homes (that you can actually stay in) at nearby Fort Worden State Historical Park, where Officers Row offers giant houses with sweeping views of Puget Sound. To get out on the Sound, hit up the Northwest Maritime Center, which offers free boat tours and kayak rentals. It’s a great way to see the city the way mariners and merchants did back in Port Townsend’s 19th-century heyday. If you’re still craving more time outdoors, Port Townsend is just over an hour from Olympic National Park.
Park City, UT
19. Park City, Utah
Park City’s 1800s Western aesthetic attests to the town’s roots as a major mining center. But when a drop in silver prices threatened its livelihood in the middle of the last century, the state of Utah decided to promote the area as a ski destination instead. Park City Resort opened in 1963 with a gondola running right from the town. Another big change came in 1981 when the Sundance Film Festival, started a couple years earlier in Salt Lake City, moved its location to Park City.
A few decades later, Park City has evolved into the coolest town in Utah, offering plenty of world-class restaurants and shops to meet the demand of skiers and the thousands of annual Sundance attendees. Even after the festival ends in early February, Park City has plenty to do: In winter, the Park City Mountain resort is now much larger while the upscale Deer Valley Resort is a five-minute drive up the road. Summer activities include everything from whitewater rafting to horseback riding, with much fairer temperatures than the desert landscape a few hours south. And if you’re worried about being able to grab a drink that isn’t a 3.2% beer (it’s still Utah, after all), Park City has you covered. The High West Distillery is the world’s only ski-in distillery, where you can happily lap up full-strength whiskey without fear of the Zion Curtain.
Traverse City, MI
20. Traverse City, Michigan
People outside of the Midwest don’t really think of Michigan as being a state full beach towns, but spend a summer weekend in Traverse City and you’ll probably start looking down your nose at Florida. No beach town in America brings big-city-level wine, beer, and food like Traverse City. It sits at the end of the Leelanau Peninsula, one of the top wine destinations in the Midwest. Here, you can spend the day sipping wine then watch the sunset from the beach at Sleeping Dunes National Lakeshore. Or if you prefer your beaches with dayclubs and volleyball nets, hit the Holiday Inn West Bay Resort, about as close to Mallorca as you’re gonna get on the Great Lakes.
In town, it’s all about the beer, whether you’re sipping pints at the famous 7 Monks Taproom or perusing some of the other lively suds-slingers like Filling Station, Brew, Right Brain, or Terra Firma. In Traverse City, you can sample international cuisine as easily as you would in a bigger city, whether it’s Italian at Trattoria Stella from James Beard-nominee Myles Anton, Mexican at Spanglish, or Asian-Latin fusion at Georgina’s. Though no trip here is complete without a trip to Frenchie’s Famous, an unassuming breakfast/lunch spot that’s a celebrity-chef favorite.
21. Franklin, Tennessee
Don’t you dare call it a Nashville bedroom community. Sure, it’s a scant 20-minute drive down I-65 from Music City, but Franklin has its own downtown, music festivals, history, and identity. It’s also got laws banning paparazzi, which is why celebs like Justin Timberlake, Tim McGraw, and Alan Jackson call the area home. JT helped bring the Pilgrimage Music Festival to town, which has become one of the biggest festivals in the state. And the live music at spots like Puckett’s Grocery and Gray’s On Main, as well as at the weekly summer outdoor concerts, are on par with what you’ll find 20 minutes north.
The historic downtown maintains its small-town USA character, and though the city was the site of one of the most famous battles of the Civil War, the only remnants you’ll find are in the historic battlefields throughout town. Franklin also has all the big-city amenities one might find in Nashville, whether it’s beer at Mantra, distilleries at Leiper’s Fork and H Clark, or wines at Kix Brooks’ Arrington Vineyards. Franklin’s regularly features on “best places to live and raise families” lists, but don’t let that to deter you if you’re not at that stage yet; Franklin is anything but boring, and it’s absolutely worth a side trip on your next visit to Nashville. Plus, we guarantee you’ll run into significantly fewer bachelorette parties.
Santa Cruz, CA
22. Santa Cruz, California
College students know Santa Cruz as the home of University of California’s very chill UCSC campus in the forest of the Santa Cruz Mountains, which are packed with hiking trails. Surfers know it as one of the very best surf spots in the world as reefs and kelp beds along craggy coastline make for exceptionally consistent waves for every skill level. Kids know Santa Cruz for its old-fashioned beach boardwalk, boasting a 1924 wooden roller coaster that should be on any adrenaline junkie’s bucket list.
Spanning the upper edge of Monterey Bay, Santa Cruz also has some of the best weather on the Northern California coast, as its coastal mountain range and the bay’s topography protect it from the summer fog that socks in a lot of the coastline in either direction. With local farms and ranches so close by, and a dedication to sustainable dining, you also have incredible farmers markets and restaurants. Add a hip downtown with bars and music venues, and there’s not much else you could possibly want in a seaside town.
23. Fayetteville, West Virginia
Hold your West Virginia jokes, please, because when it comes to mountain scenery and hardcore adventure, nowhere east of the Mississippi tops West Virginia. It’s captured best in Fayetteville, the jumping off point — sometimes literally — for the New River Gorge. It’s a short drive from the most treacherous whitewater in the East along the New River, which flows under the iconic New River Gorge Bridge. Every October the bridge hosts Bridge Day, when all the bungee jumpers, base jumpers, and other people who find leaping off an 876-foot bridge to be a good use of their time converge to take the leap.
Fayetteville is also chock full of food to indulge in after a hard day of action. Pies and Pints is the sort of creative-pizza-and-beer gem you expect to discover in a Rocky Mountain college town and might be the culinary highlight of the state. For something more upscale, grab a craft cocktail at The Station, a converted gas station that now serves ribeyes, wild salmon, and local dry-rubbed pork chops in its romantic dining room. Or grab a sandwich at one of the best sandwich shops in America at Secret Sandwich Society.
24. Waimea, Hawaii
Waimea, on an inland plateau at the north end of the Big Island of Hawaii, is where the cowboy West meets old school Hawaii. It’s home to Parker Ranch, the largest ranch in Hawaii and employer of many of the town’s residents. Here, you’re as likely to see a paniolo, or Hawaiian cowboy, cruising through town on his horse as you are a surfer with a board under her arm. You can have a go at horseback riding through the lush Waipi’o Valley yourself with Waipi’o on Horseback.
With an elevation over 2,600 feet, Waimea is cooler than the island’s coastal towns. It also lies at the crossroads of the Big Island’s lush and wet windward side and its sunny and dry leeward coast — everything grows here. It holds one of the best farmers markets you’ll ever go to and is packed with farm-to-table restaurants that are consistently rated as some of the best on the islands. In short, it’s a chiller, realer Hawaii than the tourist-packed beaches elsewhere in the state. Here, you can actually relax and soak up good island vibes instead of being harassed with leis at a resort luau. (A side note: Kauai and Oahu also have towns named Waimea, and no shade to those towns, but we’re recommending the Waimea that’s also sometimes called Kamuela. Less confusing, right?)
Asbury Park, NJ
25.Asbury Park, NJ
We try not to play favorites, but Asbury Park is the only city that’s made it onto our list of Coolest Towns three years in a row. Each time we look back expecting it to have sold out or been overrun with tourists and high-rise condos, yet each year, it continues to deliver new surprises in the form of live music, diverse food, an insanely good bar scene, and real Jersey Shore vibes where everyone keeps their fists planted firmly around a drink.
Once a grungy town with ghostly relics of the Jersey Shore’s golden days — the dilapidated Paramount Theatre and Convention Hall, defunct casino and carousel, and empty boardwalks without amusements — Asbury Park has exploded in the last decade as the cultural hub of the Jersey Shore. Here, independent musicians rock out at the same sticky-floored venues that gave acts like Bruce Springsteen and the E Street Band their start. There’s always live music happening nightly, whether at the iconic Stone Pony, The Saint, or the recently reopened music venue/bowling alley Asbury Lanes. One of the coolest music events to emerge is the Shadow of the City festival, helmed by Bleachers frontman Jack Antonoff, which features young, up-and-coming indie artists and the occasional throwback early-‘00s favorite.
The famed Wonder Bar now hosts a very popular Yappy Hour, during which people can bring their doggos to the sandy outdoor patio. At Porta, guests sit at communal picnic tables to nosh on wood-fired pizza (probably the best in the state), sip on craft cocktails, and maybe even dance to a DJ set at night. The Asbury Festhalle & Biergarten serves standard German fare with a ton of draft beer options, and the infectious, convivial atmosphere makes it the best place to go out with a group in all of NJ. Stay at any of these bars long enough, though, and you’ll inevitably end up stumbling into Johnny Mac’s at 1:00 AM for the free pizza that comes with your drink.