• How do we define 'Coolest Small Town'?
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Phoenicia, N.Y. (Pop. 388)
Two and a half hours north of New York City, this tiny town in the Catskill Mountains is a smaller version of nearby Woodstock: quiet and rural, with a hippie vibe and an artsy edge. Phoenicia's main drag is humbled by panoramic views of the magnificent 286,000-acre Catskill Forest Preserve, but surprisingly trendy stores line the street, like Mystery Spot Antiques—packed with vintage clothing, out-of-print books, and quirky housewares—and the Arts Upstairs, a seven-room gallery of original works, often by local artists. Thanks to a wealth of ex-Manhattanites who settled here a decade ago, Phoenicia has plenty of quality restaurants. Sweet Sue's may look like a regular diner, but the line of locals out the door should tip you off: The brunch menu includes renowned home fries and 25 types of pancakes, like pumpkin, mixed berry, and even carrot.
Clayton, N.Y. (Pop. 1,890)
This historic shipbuilding center lies on a tiny peninsula in the middle of the Thousand Islands, a remote archipelago dotting the St. Lawrence River along the Canadian border. Known for its lush greenery and surprisingly clear waters, Clayton thrived as a millionaires' retreat in the late 1800s. Today, those lavish homes are a draw in themselves. The city's historic downtown boasts restored brick buildings clad with original window crowns and cast-iron cornices, many of which house shops and hotels like the red-and-white Thousand Islands Inn, built in 1897, and the River Rat Cheese Shop, where you can pick up local white cheddar from nearby Gold Cup Farms. In the summertime, the old ferry terminal, which once shepherded wealthy visitors to their island cottages, now hosts waterfront concerts. Out on the river, the family-run Ferguson Fishing Charters offers morning fishing trips, followed by picnics on a deserted island, where a guide cooks the day's catch over a fire. For dessert: Eggs, sugar, cream, and bread are tossed into the hot grease, creating a French-toast-like puff pastry that's topped with butter, maple syrup, cream, and brandy.
Wiscasset, Maine (Pop. 4,489)
In this village along the tidal Sheepscot River, U.S. Route 1 serves as Main Street, crowded with gourmet food shops and antiques dealers. In the warmer months, the brick walkways and 18th-century buildings are adorned with brimming flowerpots. Tourists wander in and out of the town's nearly two-dozen antiques stores, where locals hawk American folk art, quilts, and 1950s board games. Wiscasset is planning to edge into the future soon with a new hydropower plant, which will be the largest clean-energy development in the history of the state. The town's main attraction, though, is Red's Eats, a rickety hut on the water that serves up lobster rolls stuffed with a pound of fresh meat. Bed-and-breakfasts dot the surrounding area, the most notable of which is the family-friendly Snow Squall Inn, owned and run by a former chef who now prepares breakfasts for his guests each morning. For those who want to sleep under the stars, Chewonki is the crème de la crème of campgrounds. It has a pool, a tennis court, boat rentals, and 47 spacious sites along Montsweag Brook.
Newtown Borough, Pa. (Pop. 2,384)
Located in Pennsylvania's rural Bucks County, between NYC and Philadelphia, Newtown Borough was founded by William Penn in 1684—and hasn't changed a whole lot since. The area is surrounded by peaceful, rolling farmland, and the two-lane roads are frequented by Amish horses and buggies. In town, State Street is lined with wide sidewalks, flower gardens, and boutiques like the Rose Cottage Needlepoint Studio crafts shop and Ned's Cigar Store, a tobacco outlet run by two friends who won the lottery (one the Cash 5, the other a scratch-off) and bought the store with their winnings. Newtown is also home to the oldest movie theater in the country, with just one screen, along with some standout restaurants: As one of our readers noted, "Oishi, for instance, is the best Japanese restaurant I've ever been to—and I live in Manhattan!"
Alpine, Tex. (Pop. 6,460)
Alpine is surrounded by the rugged trappings of an old Hollywood western—high desert scrub, red mountains, canyons, and vast cattle ranches. But while it may look like a movie set, this small West Texas outpost is actually an authentic center of cowboy culture, with spots like the Big Bend Saddlery just waiting to fulfill all your belt and buckle needs. February brings the annual Texas Cowboy Poetry Gathering, a three-day celebration of the fireside oral tradition. Just outside of town, at Woodward Ranch, amateur gem hunters can dig for semiprecious stones—the ranch charges for finds by weight. Back in Alpine, locals cool off at the Murphy St. Raspa Co., a funky spot specializing in raspa, or Mexican shaved ice. The adventurous can spice up their snow cones with outlandish toppings like chili powder, Fun Dip, chamoy (a mix of pickled apricots and plums), and even diced pickles.
Lewisburg, W.Va. (Pop. 3,497)
This Allegheny Mountains town is heralded for two major food events: In April, the mayor dresses up like Willy Wonka for the Lewisburg Chocolate Festival, which celebrates all things cocoa with a week of chocolate-themed tastings and dinners. October brings the Taste of Our Towns (or TOOT, as the locals call it), when restaurants dish out their best-known items at food stands scattered downtown and live bands play on three open-air stages. Annual favorites like the General Lewis Inn's pecan pie disappear fast. The town is also home to one of only four Carnegie Halls (carnegiehallwv.com) in the world, which draws big-name musicians and theater productions to the remote area. And just this past September, rock-violin band the Dueling Fiddlers shot a music video at local wine bar Red Key 3.
Cedar Key, Fla. (Pop. 954)
While much of Florida has become overrun with theme parks, strip malls, and luxury condos, the fishing village of Cedar Key—with its abundance of pelicans, palmettos, and Spanish moss—is a vivid reminder of the state as it once was. Two long-forgotten forms of architecture dominate the cay: 19th-century wood-frame cottages with wraparound porches, and tabby houses, made with a combination of sand, water, and crushed shells. Cedar Key also holds the distinction of being the nation's number one producer of farm-raised clams. Locals swear by the award-winning chowder at Tony's Seafood Restaurant, and there are dozens more dockside eateries where you can sample fresh Gulf shrimp, oysters, and grouper. Outside of town, 13 islands make up the Cedar Keys National Wildlife Refuge, where kayakers can spot frigate birds, ibis, and bald eagles.
Eureka Springs, Ark. (Pop. 2,390)
As the only town in the country with its entire zip code listed in the National Register of Historic Places, this southern Ozarks hamlet celebrates its past, from the immaculate Victorian houses lining Main Street to the painstakingly preserved homes hugging the cliffs outside town. There are zero traffic lights and shopping malls within city limits. The Springs—as locals call the town—was once the stomping grounds of Jesse James and his gang, before cleaning up its act and becoming a spa destination at the turn of the 20th century. Today, some 60 natural hot springs still make Eureka Springs a magnet for health centers: There are six spas and more than 50 registered massage therapists and alternative healers. In between spas and Victorian mansions, old-fashioned trolley cars zip along the streets, providing free rides. Outside the city limits, Pivot Rock Park's deep ravines, caves, and natural bridge draw hikers, while the nearby Turpentine Creek Wildlife Refuge—the world's largest sanctuary for big cats—allows visitors to see white Bengal tigers, cougars, and lions up close.
Greensburg, Kans. (Pop. 1,200)
Around 9:30 p.m. on May 4, 2007, a category EF5 tornado—the strongest designation twisters can receive—ripped through the tiny town of Greensburg and leveled everything in its path. Winds reached 205 mph, destroyed 95 percent of Greensburg's buildings, and severely damaged the remaining 5 percent. That kind of destruction would be enough to knock most towns off the map. But in Greensburg, locals in the tight-knit community dug their heels in and immediately set to work rebuilding their beloved hometown. The city council voted to rebuild all structures according to Leadership in Energy and Environmental Design (LEED) platinum standards, making Greensburg the first town in the U.S. to do so—and effectively creating a new model for green, small-town redevelopment. And its environmental strides even encompass the arts: Greensburg's 5.4.7 Arts Center, the only public art museum between Wichita and Dodge City, is entirely solar- and wind-powered.
La Pointe, Wis. (Pop. 285)
The only town on the only inhabited island in Lake Superior's Apostles archipelago, La Pointe is a close-knit community filled with galleries and artists' workshops. The heart and soul of the town, though, is Tom's Burned Down Café, a lakeside "bar" consisting of nothing more than a large tent covering an open-air deck. Opened in the 1950s by a notorious Chicago divorcée, Tom's burned down in the '90s—rumor has it, the owner set it aflame to collect the insurance money. But still, the bar prevailed: By noon the next day, a local had cleared away the ashes and filled the deck with beer. Patrons were back that very night. Now, each year, the tent goes up around Memorial Day, and all summer, residents and tourists come for nightly music that ranges from Celtic fiddles to country rock. In January, when the lake freezes over and the ferry can no longer make the 25-minute trip to Madeline Island from the mainland, people drive cars across Lake Superior, following a trail marked by locals' old Christmas trees.
Ripon, Wis. (Pop. 7,479)
Set smack in the middle of Wisconsin, about 90 minutes northwest of Milwaukee, Ripon is a traditional, rural community steeped in history. Leading up to the Civil War, the pro-abolition Republican Party was founded here, and many original buildings from that era still stand. For the past 20 years, an aggressive downtown revitalization program has transformed Ripon's historic district into a vibrant retail center, and more recently, a Milwaukee-based developer announced plans to invest at least $40 million in downtown renovations, including purchasing old storefronts and converting them into upscale restaurants and apartments—and installing a Wi-Fi system that will cover the entire town. When the weather is warm, Ripon's locals congregate for special events, like the Friday-night free concert series, the blowout sidewalk-sale weekend on Maxwell Street, and an Oktoberfest in September, complete with microbrewed beer, brats, and classic car shows. But perhaps nothing is celebrated more here than baked goods: Rippin' Good Cookie bakery is a local favorite with undergrads at Ripon College, and in 1994, the town collectively set a record for baking the world's largest cookie—measuring in at 907.9 square feet—a feat now commemorated every summer with a big festival.
Victor, Idaho (Pop. 1,159)
Across the rugged Teton Valley, the tonier ski town of Jackson, Wyo., tends to get all the attention (and the celebrity visitors). But locals here make a clear choice for the more low-key community of Victor. The jagged peaks of the Tetons loom over Victor's meadows and streams, and the broad Main Street is flanked by Old West–style storefronts. The Victor Emporium has been serving its famous huckleberry milkshakes for more than 50 years, and Pierre's Playhouse hosts movies, concerts, and plays. In the summer, there's golf at Teton Springs' Headwaters Club, fly-fishing on the Snake River, and open-air movies screened at the Spud Drive In. In the winter, Victor's resident ski-film companies head to the nearby slopes at Jackson Hole Mountain Resort and Grand Targhee Resort.
Cooke City, Mont. (Pop. 142)
Just four miles from Yellowstone National Park's seldom-used northeast entrance (no long lines—even in peak summer season!), Cooke City shares the park's renowned geography and wildlife. Bears, moose, buffalo, and elk roam the pristine Alpine forests just outside town, and the trip into Cooke City is an epic introduction: From the city of Red Lodge, you drive along the Beartooth All-American Road, which swoops up and over the snowcapped Rockies on the way into Cooke City. Main Street anchors a loose gathering of locally run outfits like the general store, and log cabins are scattered all over town. Some are private residences, while others are for rent, like the Antlers Lodge's 18 structures, which surround a central 1913 cabin. Despite its tiny size, Cooke City hosts a massive fish fry every summer, an annual tradition since the 1920s. Year-round, the family-run Buns "N" Beds offers fresh BBQ smoked right on the premises.
Salida, Colo. (Pop. 5,433)
This adventurer's paradise, three hours southwest of Denver, is an unexpected oasis of activity surrounded by abandoned mining communities. Salida's unique setting helped it escape the fate of its ghost-town neighbors: Of the 50-plus mountains in Colorado that rise above 14,000 feet, 15 of them encircle Salida, creating a climate ripe for year-round outdoor sports, including biking, skiing, kayaking, and—what the city is best known for—white-water rafting. Each year, Salida hosts FIBArk on the Arkansas River, the oldest white-water festival in the country, run since 1949. Recently, the town has been gaining just as much attention for its burgeoning arts scene. Blocks lined with colorful Victorian buildings make up the largest historical district in Colorado, a fitting spot for the annual Art Walk, a three-day showcase of local talent. Salida's food offerings can be just as creative. New grocery store Ploughboy sells only organically grown, local foods, including tilapia produced in the prison aquaculture program in nearby Canon City. Former Iron Chef America contestant Kurt Boucher puts French and Asian touches on fresh ingredients and wild game at the Butcher's Table. And for a slight change of pace, visitors can retreat to the Tudor Rose B&B, a country manor with Rockies views.
Bluff, Utah (Pop. 320)
Many consider Bluff to be a lot like Moab before it took off. The community is located in the verdant San Juan River valley, bordered by 300-foot-high sandstone bluffs, rolling ranchland, and the Navajo Nation. In fact, some of the most sacred Native American sites in the country, like the rock art and ruins of the ancient Anasazi culture, are just outside the city limits. In Bluff, there are carefully restored old pioneer homes open for tours, along with a surprising number of quality lodges and B&Bs for such a tiny town, like the Desert Rose Inn, a timber lodge with a two-story wraparound porch and expansive red-rock views. In recent years, white-water rafting enthusiasts have discovered Bluff, and a number of outfitters, like Wild Rivers Expeditions, have set up shop here, offering outings to the Class IIIs along the San Juan.
Bolinas, Calif. (Pop. 1,238)
Tucked away among coastal eucalyptus groves an hour north of San Francisco, Bolinas is the sort of fiercely independent bohemian community people have come to expect from northern California. Once home to counterculture luminaries like '60s rock band Jefferson Airplane and beat poet Lawrence Ferlinghetti, this hamlet has only grown feistier in the decades since. Bolinas can be reached solely by unmarked roads—and that's by design. The unofficial "border patrol" is so dedicated to keeping the town locals-only that its "officials" steal any highway signs that make it easier for tourists to invade. (Reportedly, no sign has lasted longer than 36 hours.) It's not hard to see why residents want to keep Bolinas a secret. Its peaceful beaches are a favorite of novice surfers, as well as large populations of herons, egrets, and harbor seals, and its bars and eateries are as good as any you'd find in the Bay Area: Smiley's Schooner Saloon is one of the state's oldest continuously operated bars, established in 1851, and the Coast Café serves super-fresh mesquite barbecued oysters, sourced from nearby Drakes Bay.
Astoria, Ore. (Pop. 9,738)
Consider this small Pacific Coast town a miniaturized version of San Francisco—its architecture is dominated by Victorian homes clinging to steep wooded hillsides, its weather is mild year-round, and its hip local hangouts make for a hot nightlife scene. Astoria sits at the mouth of the Columbia River, and the area's temperate rain forest is home to bald eagles and brown pelicans. As the oldest town west of the Rockies—the area was first settled by none other than Lewis and Clark—Astoria started out as a roughneck port, populated by sailors and cannery workers. Today, that crowd has largely been replaced by artists and indie-rock musicians, but the freewheeling vibe remains. Nightly shows at live-music venue the Voodoo Room bring in big-ticket acts, and artisanal coffeehouses, galleries, and boutiques occupy the 1920s buildings downtown. One highlight: The waterfront Columbia River Maritime Museum has stirring exhibits devoted to hundreds of shipwrecked boats, victims of the Oregon coast's sometimes violent swells.
Port Townsend, Wash. (Pop. 9,136)
Set on Puget Sound, with the jagged Cascade Range as its backdrop, postcard-perfect Port Townsend is a bustling seaport and artists' community rolled into one. Along the water, kayakers bob between industrial ships ferrying wares to Seattle, 40 miles southeast, and beyond. In town, the streets are lined with 19th-century architecture, including the Jefferson County Courthouse, a redbrick stunner considered one of the best-preserved Victorian structures in the country. Down the block, the Fountain Café serves fresh seafood and homemade pastas out of a mint-green 1889 building, alongside countless galleries. In the warmer months, local artists set up easels around town to paint the surrounding landscape: The peaks and rain forests of Olympic National Park are a few minutes west, and the San Juan Islands are a quick boat ride to the north.
Talkeetna, Alaska (pop. 1,062)
This former gold-mining hub, about two hours north of Anchorage, is best known as the base camp for the adventurous hoping to climb all 20,320 feet of nearby Mount McKinley—North America's tallest. Somewhere between 500 to 800 climbers summit the peak each year, but not all of them fare so well. In fact, Talkeetna's cemetery contains a Mount McKinley Climbers' Memorial to those who perished in their attempts—scattered throughout, in place of regular tombstones, visitors will find propellers poking out of the ground, which mark the graves of bush pilots. For those who like their adventures a little less daring—but just barely—the West Rib Pub & Grille offers the five-pound Seward's Folly burger, made up of two pounds of caribou, sliced ham, 12 slices of bacon, and 12 slices of cheese. Each year, residents look forward to the Moose Dropping Festival, a singular gambling event in which varnished pieces of moose dung are flung from a helicopter after residents bet on where they will land. (In 1989, Talkeetna made national headlines when an outraged PETA representative misunderstood and thought live moose were being dropped from helicopters.) No wonder this undeniably quirky town is said to be the inspiration for Cicely, the fictional setting of the '90s cult-classic comedy Northern Exposure.
Haleiwa, Hawaii (Pop. 2,285)
This North Shore beach town is less than an hour's drive from Honolulu, but it's far enough removed to retain a low-key vibe all its own. The resident surfers and artists are completely laid-back and unpretentious. Anything other than flip-flops looks way too fancy, and anything other than a beach-cruiser bike on the little oceanfront path looks way too intense. In the morning, everyone gets their caffeine fix at Coffee Gallery, a locally owned nook that also serves baked goods like maple blondies topped with bacon crumbles. In the afternoon, the surfers head to Surf N' Sea to get their boards waxed or to replace their leashes before taking on the legendary North Shore breaks, while the more mellow head to the beachside Shark's Cove Grill food cart to load up on peanut-butter-and-banana smoothies or a platter of Portuguese sausage, eggs, and rice, and then watch the waves from the safety of the sand.
How do we define 'Coolest Small Town'?
The town must have a population under 10,000—we're talking small towns, not big cities. It's also got to be on the upswing, a place that's beginning to draw attention—and new residents—because of the quality of life, arts and restaurant scene, or proximity to nature. And cool doesn't mean quaint. We want towns with an edge, so think avant-garde galleries, not country stores.