100 Coolest Small Towns in America From the redwood forests to the Gulf Stream waters, nobody celebrates the best in small-town America like Budget Travel. Meet a decade's worth of winners of our annual Coolest Small Towns contest! Budget Travel Friday, Jan 15, 2016, 6:00 PM Grand Marais, Minn. (Winner 2015): Get your canoe on! Here on the north shore of Lake Superior, the Boundary Waters Canoe Area is one of the world’s perfect paddling destinations, with miles of waterways to navigate. (Courtesy Visit Cook County Minnesota) Budget Travel LLC, 2016
 

VACATION IDEAS

100 Coolest Small Towns in America

From the redwood forests to the Gulf Stream waters, nobody celebrates the best in small-town America like Budget Travel. Meet a decade's worth of winners of our annual Coolest Small Towns contest!

  • Hjordis, a sailboat, sailing near Grand Marais, MN
  • Riverwalk in Hillsborough NC
  • Saltwater Cowboys in Chincoteague, VA
  • The main street in Snohomish, Washington
  • Lakefront View in Huron, OH
  • Fishing at Havens Gardens Park on the Pamlico River of Washington, NC
  • Times Square in Fort Myers Beach, considered the heart of Estero Islands downtown with shops, restaurants and the Fort Myers Beach Pier
  • Main Street in Allegan, Michigan
  • The Pier at Old Orchard Beach, Maine is a popular summertime destination visited by people from all over the world. Located on the coastline of the Atlantic Ocean.
  • Snowy gazebo on the Courthouse Square
  • Fiddlers in Berlin, Maryland
  • Lakeland park fountain and stage overlooking Cazenvoia Lake, Cazenovia NY
  • Biking along Swamp Rabbit Trail
  • Zimmerman Boatyard marina is known as a world class yard specializing in wooden boat building and repair.
  • The Nevada City Classic, one of the premiere sporting events in the Sierra foothills, takes place every year on Fathers Day.
  • Fulton Mansion and Education Center -George and Harriet Fulton began construction in 1874 on their spacious and extravagant home overlooking the Aransas Bay. Completed in 1877, the house featured ornate trim work and furnishings and the latest technological conveniences including modern plumbing, central heating and a gas lighting system.
  • Estes Park has a thriving, and inviting, downtown.
  • The Yadkin Riverkeeper hosts this annual event each June, where paddlers journey down the Yadkin River and stop for 3 days in Elkin.
  • View of the popular tourist destination of Galena, Illinois during a busy summer day.
  • The Downtown Historic District in Buckhannon features specialty shops and boutiques, fresh food served up at local restaurants and a classic small-town atmosphere.
  • Congregational stores in Lititz, Pennsylvania
  • Hot air balloons in Greenville, Kentucky
  • An aerial view of Gulf Shores, Alabama
  • Aerial view of Put-in-Bay, Ohio
  • Flagler Beach Florida
  • Sailing ship in front of Curtis Island lighthouse at Camden, Maine of a perfect early Autumn day
  • Bay St Louis, Mississippi, Beach Blvd
  • Quincy, California
  • Shepherdstown Sweet Shop and Bakery
  • Vintage Grand Prix Festival. Downtown Watkins Glen
  • A live music performance along the Front Street docks of Beaufort, NC
  • Swimming in Keuka Lake, Hammondsport, NY
  • Cooke Citys trash-dump-turned-museum
  • The town of Jerome, built on Cleopatra Hill
  • Boats moored at the town dock in Port Townsend, WA
  • Bicycling by the Cape May General Store in Cape May Point, NJ
  • Muddy Boots Cafe, a favorite breakfast spot
  • Historic Main Street, which dates back to the Gold Rus, in Weaverville, CA
  • Old Brick House Restaurant in Ste. Genevieve, MO. Originally erected in 1780 and is the oldest brick building west of the Mississippi
  • The Lazy Fox Inn in Damascus, Virginia, which provides a famously hearty breakfast for hikers on the Appalachian Trail
  • Lewisburg, WV
  • Astoria, OR
  • Clayton, NY
  • Eureka Springs, AR
  • Le Point, WI
  • Phoenicia, NY
  • Newton Borough, PA
  • Cedar Key, FL
  • Ripon, WI
  • Greensburg, KS
  • Ely, MN
  • Cloverdale, CA
  • Brevard, NC
  • Saugatuck, MI
  • Kennett Square, PA
  • Bandon, OR
  • Cuero, TX
  • Nyack, NY
  • Medicine Park, OK
  • Egg Harbor WI
  • Cayucos, CA
  • Lexington, VA
  • Breaux Bridge, LA
  • Tubac, AZ
  • Wallace, ID
  • Saugerties, NY
  • Mount Vernon, IA
  • Jacksonville, OR
  • Rockland, ME
  • Whitefish, MT
  • Port Jervis, NY
  • Manitou Springs, CO
  • Yellow Springs, OH
  • Mazomanie, WI
  • Point Reyes Station, CA
  • Belfast, ME
  • Catskills, NY
  • Truth or Consequences, NM
  • Livingston, MT
  • White River Junction, VT
  • Millerton, NY
  • Milford, PA
  • Yachts, OR
  • Waitsburg, WA
  • Paia, HI
  • Parkville, MO
  • Silver City, NM
  • Petersborough, NH
  • Tuscumbia, AL
  • Collinsville, CT
  • Barnard, VT
  • Murphys, CA
  • Homer, AK
  • Bisbee, AZ
  • Fayetteville, WV
  • Hudson, NY
  • Great Barrington, MA
  • Rocheport, MO
  • Marfa, TX
  • Hood River, OR

Grand Marais, Minn. (Winner 2015): Get your canoe on! Here on the north shore of Lake Superior, the Boundary Waters Canoe Area is one of the world’s perfect paddling destinations, with miles of waterways to navigate.

(Courtesy Visit Cook County Minnesota)

Hillsborough, N.C. (Winner 2015): Art and literature come alive in the mountains. The town has serious literary cred, with several bestselling authors not only making their home here but also participating in local events and the annual production of “A Christmas Carol.”

(Courtesy Donn Young/Orange County Visitors Bureau)

Chincoteague, Va. (Winner 2015): This incredibly beautiful island town offers a mid-Atlantic summer getaway complete with perfect beach­es with trails for cycling and walking, fresh seafood (and an annual seafood festival!), and its legendary wild ponies.

(Courtesy Chincoteague Chamber of Commerce)

Snohomish, Wash. (Winner 2015): With idyllic rolling farmland, Puget Sound, and the Cascade Mountains as a backdrop, this town is a Pacific Northwest paradise just a short drive from Seattle. Activities here are as big as all outdoors, with hot-air ballooning, sky-diving, and unique local festivals such as “GroundFrog” Day and the Easter Parade, with its Sauerkraut Band.

(Courtesy Snohomish County Tourism Bureau)

Huron, Ohio (Winner 2015): Where the Huron River meets Lake Erie, one of the Midwest’s hidden gems is waiting for you. Go hiking at Shel­don Marsh State Nature Preserve, visit the Huron Pier for some great fishing, relax on Nickel Plate Beach, or hit the local golf course.

(Robert Myer)

Washington, N.C. (Winner 2015): Locals like to say that Washington has a small-town feel but big-town activities. The waterfront downtown is a major draw, with a renovated theater, wonderful shops, and a wine-tasting scene that surprises some visitors.

(Courtesy Little Washington NC)

Fort Myers Beach, Fla. (Winner 2015): Here, everybody knows everybody, and you’re never more than a mile or so from the sparkling waters of the Gulf of Mexico. Think of this as your entry point for exploring this remarkable stretch of coast­line, including gorgeous islands, Everglades National Park, and creatively prepared local seafood at restaurants such as The Beached Whale and Matanzas on the Bay.

(Jccain/Dreamstime)

Allegan, Mich. (Winner 2015): Locals sometimes refer to Allegan as a “modern-day Mayberry,” and we can understand why. Friendly eateries like The Grill House, Minnie Sophrona’s Restaurant, and Corky’s Drive-In, plus an old-timey movie theater and much more, make visitors feel at home here.

(Courtesy Chris Light/Wikimedia Commons)

Old Orchard Beach, Maine (Winner 2015): There’s more to this town than its namesake beach, though truth be told the seven-mile stretch of sand is awesome in its own right, with its legendary amuse­ment park and nightlife that includes live bands and great seafood.

(Vtphotos/Dreamstime)

Delhi, N.Y. (Winner 2015): The western Catskills in Upstate New York make for a wonderful setting, with rolling hills and the Delaware River (yes, its west­ern branch reaches all the way up here) flowing through town. A thriving Main Street is ideal for browsing eclectic gal­leries, antique shops, and an artisan guild that features local talent.

(Molly Oliver)

Berlin, Md. (Winner 2014): Not far from Maryland's teeming Ocean City and gorgeous Assateague Island, Berlin's downtown is a National Register Historic District and plays host to fun events all year long, from the regular farmers market to one-of-a-kind bashes like the Berlin Fiddlers Convention, New Year's fireworks, Victorian Christmas (complete with horse-drawn carriages), and, yes, even bathtub races.

(Courtesy Worcester County Tourism)

Cazenovia, N.Y. (Winner 2014): If Central New York isn't already on your travel radar, get ready for a big, and very pleasant, surprise! Cazenovia, on the shores of Cazenovia Lake, may make you feel like you've discovered the perfect small town you thought didn't really exist. Start with a stroll down Albany Street to get a sense of the community's long history, with architectural styles dating back to New York's colonial days.

(Courtesy Greater Cazenovia Area Chamber of Commerce)

Travelers Rest, S.C. (Winner 2014): Travelers Rest gets its travel-mag-ready moniker from the pioneer days, when travelers followed a trail dotted with the occasional tavern or inn. But the town offers not only restful, comfy lodgings but also world-class outdoor activities. Nearby state parks and bike trails (including the legendary 13.5-mile Swamp Rabbit Trail) basically invite you stay outdoors all day long.

(Courtesy Travelers Rest Tribune)

Mathews, Va. (Winner 2014): Mathews is not just a town but also Virginia's second smallest county, with just 84 square miles and no traffic lights. But we know "small" and "cool" go together like beaches and cottages. Speaking of which, Mathews includes miles of Chesapeake Bay shoreline that make it a prime summer destination for beachgoers, bird watchers, cyclists, fishermen, and kayakers.

(Boo Schwartz )

Nevada City, Calif. (Winner 2014): Nevada City may be a little off the beaten path (60 miles northeast of Sacramento, in the foothills of the Sierra Nevada Mountains), but residents value the Gold Country town for its music and art scene, food, and proximity to some of California's amazing rivers, lakes, and the Sierras.

(Courtesy Nevada City Classic)

Rockport, Tex. (Winner 2014): Never heard of Rockport? Well, we hadn't either, which just means it's now not only a candidate for Coolest Small Town but also for one of our best-kept secrets. Here, artists, saltwater fishermen, and birdwatchers have been lured to Texas's warm Gulf coast.

(Courtesy Rockport-Fulton Chamber of Commerce)

Estes Park, Colo. (Winner 2014): When your town is the headquarters for Rocky Mountain National Park, you've got a pretty good head start on other cool burghs. Skiing and snowshoeing the surrounding mountains is a must in winter, and rafting, fishing, and wildlife viewing are on tap in warmer months (if you're lucky, you'll catch a glimpse of the iconic bighorn sheep with its curved horns).

(Courtesy Visit Estes Park)

Elkin, N.C. (Winner 2014): In the lovely Yadkin Valley Wine Region of North Carolina, Elkin is about one hour north of Charlotte in the foothills of the Blue Ridge Mountains. Here, you'll find just about every outdoor activity you might like, including hiking, kayaking, canoeing, fishing, birdwatching, and cycling.

(Courtesy Town of Elkin)

Galena, Ill. (Winner 2014): Nestled among rolling hills along Illinois's Galena River, this bustling town has a thriving downtown with unique boutiques, antique shops, art galleries, and restaurants. Visit one of the area's three local wineries, hike the easy, beautiful hills just outside town, kayak the gentle rivers, and golf at one of the state's most prized courses.

(Dustin88/Dreamstime)

Buckhannon, W.Va. (Winner 2014): Whether you're rafting down the Buckhannon River, delving into local Civil War History at the Latham House, or tucking into a "hot belly" BBQ pork sandwich at CJ Maggies American Grill, Buckhannon is a charming host.

(Robbie Skinner)

Lititz, Penn. (Winner 2013): You couldn't ask for a more beautiful location, in rural Lancaster County, Penn., with its rolling farmland and traditional Amish communities. Here, you can savor 18th-century history just a 90-minute drive from Philadelphia—a perfect long-weekend destination.

(Courtesy Smallbones/Wikimedia Commons)

Greenville, Ky. (Winner 2013): That particularly Southern combination of down-home charm and old-fashioned grandeur is old hat in Greenville. Founded in 1799 and settled by Revolutionary War veterans, it grew over the next century into the seat of one of the South's most profitable coal-mining regions.

(Courtesy Greenville Tourism Commission)

Gulf Shores, Ala. (Winner 2013): Folks in this Gulf of Mexico beach town must get tired of hearing tourists do their best Bubba impersonations. But comparisons to Forrest Gump's shrimp-loving sidekick are only logical: Each October since 1971, the town hosts the National Shrimp Festival, often attracting over 250,000 people with shrimp cook-offs, concerts, and sandcastle contests.

(Courtesy Gulf Shores & Orange Beach Tourism)

Put-in-Bay, Ohio (Winner 2013): Put-in-Bay is utterly defined by its location, on South Bass Island in Lake Erie. The bay has been an essential part of lake navigation since Native Americans first plied the waters centuries ago. (The town's name likely comes from the boating term "put-in," meaning to enter the water.) The island was the site of a key naval battle in the War of 1812, and Perry's Cave, where Commodore Oliver Hazard Perry's men obtained the clean drinking water to which their victory over the British is partly attributed, is a popular historical site.

(Dan Feicht)

Flagler Beach, Fla. (Winner 2013): Twenty miles north of Daytona Beach on A1A, Flagler Beach couldn't be more different from its party-hardy neighbor to the south. In fact, the area seems to attract more sea turtles and right whales than spring breakers. And it's not hard to see why: This thin strip of a beach town, between the Atlantic Ocean and the Intracoastal Waterway, has remained significantly less developed than its neighbors.

(Courtesy Flagler Chamber of Commerce)

Camden, Maine (Winner 2013): We've all been faced with the classic vacation dilemma: the mountains or the beach? But there's no need to settle, Camden's got them both covered. This mid-coastal town located on Penobscot Bay is one of only two places on the Atlantic seaboard where the mountains meet the sea. Those gorgeous vistas have been attracting vacationers to this former ship-building town since the 1800s, when wealthy families snatched up properties to build summer homes.

(David Kay / Dreamstime.com)

Bay St. Louis, Miss. (Winner 2013): Everybody loves a comeback, and Bay St. Louis has come roaring back from Hurricane Katrina (which made final landfall near this Mississippi Gulf hamlet in 2005). Its Historic Old Town has been chugging along for 300 years (French Canadian explorers first sailed into the bay in 1699), drawing visitors to its warm beaches, first-rate fishing, and friendly vibe.

(Courtesy Ellis Anderson)

Quincy, Calif. (Winner 2013): This gold rush town on the western slope of the Sierra Nevada Mountains, where prospectors flocked in the rush of 1849, remains a mother lode of attractions for those who like to spend their days in the wild but welcome some culture and pampering in the evening.

(Courtesy of city of Quincy)

Shepherdstown, W.Va. (Winner 2013): You might say all roads lead to West Virginia's oldest town, which celebrated its 250th birthday in 2012: The Potomac River, the C&O Canal, and the Appalachian Trail all pass through this Revolutionary War-era town in the lower Shenandoah Valley.

(Courtesy Judy Olsen)

Watkins Glen, N.Y. (Winner 2013): When a community is situated among some of the most beautiful lakes in the U.S., boasts a world-class race track, and those aren't the major reasons to visit, you know you've got a cool town. Hikers and wine lovers find unparalleled trails and vineyards here, making it easy to fill a day with both sweat and style.

(Courtesy Watkins Glen Chamber of Commerce)

Beaufort, N.C. (Winner 2012): Perched on an especially serene stretch of the North Carolina coast, the town has an air of Southern gentility about it, from the restored 17th- and 18th-century buildings that flank the local historical society to the Confederate jasmine and animal topiaries that frame the Langdon House B&B.

(Christopher Shane)

Hammondsport, N.Y. (Winner 2012): You’ll find a fab wine country here in New York’s Finger Lakes region, not to mention craft beers, a funky art and coffeehouse scene, and restored vintage seaplanes.

(Arion Doerr)

Cooke City, Mont. (Winner 2012): The smallest burgh on our list, this former gold-mining town in Yellowstone country near grizzly and wolf habitats is sometimes described as the last place in the West that's still the West.

(Janie Osborne)

Jerome, Ariz. (Winner 2012): This copper mining village, once dubbed “The Wickedest Town in the West,” struck gold as an artists’ retreat. You’ll find artists’ workspaces and galleries all over town, and even the food, like blue-corn enchiladas, is bursting with color.

(Whitney Tressel)

Port Townsend, Wash. (Winner 2012): This Victorian-era seaport’s rich geographical blessings (mountains ripe for foraging, teeming fishing grounds, fertile farmlands), the region has spawned its own culinary movement: Olympic Coast Cuisine.

(PureStock/AGE Fotostock)

Cape May, N.J. (Winner 2012): America’s first beach resort offers rows of pastel Victorians, butterfly gardens, the genteel Congress Hall hotel (which also lets its hair down at The Boiler Room nightclub on the premises), and the 1970s-era Rusty Nail surfer bar.

(Whitney Tressel)

Nashville, Ind. (Winner 2012): For 100 years, this southern Indiana village did just fine as a turn-of-the-century Midwest artists' colony. Galleries and crafts studios still line the streets, the legacy of landscape painters such as T.C. Steele, who moved here in the early 1900s for the "purple haze" over the Brown County hills. The 23-room Artists Colony Inn even has palette-shaped key rings and works from the town's creative founders on its walls.

(Whitney Tressel)

Weaverville, Calif. (Winner 2012): The Far East meets the Old West here in this Gold Rush town that supplies some expected trappings, such as a saloon, main street, and hitching post, but also a working Chinese temple, a testament to the Chinese immigrants who faced discrimination in San Francisco and were welcomed here.

(Courtesy Tennysonian/Flickr)

Ste. Genevieve, Mo. (Winner 2012): The first thing you'll notice is how much Ste. Genevieve looks like a French village. And with good reason: This Mississippi River town was founded in 1740 by French Canadians, making it the first European settlement west of the Mississippi. They left behind colonial houses, built in the poteaux-en-terre (or "post-in-ground") style-also seen in Louisiana, Normandy, and Quebec.

(Ashok Sinha)

Damascus, Va. (Winner 2012): If you decide to drive to Damascus, you’ll likely be in the minority. This is hiking and cycling heaven, where seven major trails intersect, including the undulating Virginia Creeper and the granddaddy of them all: the 2,180-mile Appalachian Trail.

(Robin Macklin)

Lewisburg, W.Va. (Winner 2011): This speck on the map in the Greenbrier River Valley lays claim to one of only four Carnegie Halls in the world. Here is a view of the town square from the roof of City Hall. 

(Michael Mohr)

Astoria, Ore. (Winner 2011): Astoria has always been on the frontier, both the Lewis and Clark variety (they set up camp here in 1805) and the geographic (it sits both at the mouth of the Columbia River and in a teeming temperate rain forest). 

(Justin Bailie)

Clayton, N.Y. (Winner 2011): Some shore communities take their location for granted. Not so with Clayton, where most activities, from fishing to visiting the Antique Boat Museum, seem to revolve around the water. 

(Stephanie Adams)

Eureka Springs, Ark. (Winner 2011): This late-1800s Victorian spa retreat is known for everything from its Queen Anne–style B&Bs and its shows to its historic downtown. 

(Michael Mohr)

La Pointe, Wis. (Winner 2011): The residents of La Pointe, a quiet, North Woods enclave of artists on Lake Superior, take pride in waving hello to everyone they pass—even when they're driving. 

(Daniel Shea)

Phoenicia, N.Y. (Winner 2011): Phoenicia may look like a one-street river town sandwiched between hills in New York's Catskills, but it's got a bookish, cosmopolitan vibe in its soul. 

(Jean-Paul Bernard)

Newtown Borough, Pa. (Winner 2011): This small town is close enough to Amish Country that it's not unusual to see horses-and-buggies. It's also home to the nation's oldest movie theater, Newtown Theatre, in operation since 1906. 

(Jean-Paul Bernard)

Cedar Key, Fla. (Winner 2011): This two-square-mile hamlet 130 miles north of Tampa produces the best clam chowder outside of New England. It's also America's second-largest producer of farmed clams. 

(Stephanie Adams)

Ripon, Wis. (Winner 2011): You won't find a more utopian college town than Ripon, where students and professors form an integral part of the community. 

(Daniel Shea)

Greensburg, Kans. (Winner 2011): After a 2007 tornado destroyed 95 percent of Greensburg, those who stayed vowed to build the ecofriendliest town ever. In place of cornfields and barns, you now see wind turbines, LED streetlights, and art galleries galore. 

(Michael Mohr)

Ely, Minn. (Winner 2010): The best backyard in the country—this is a town where there are more wildlife centers (two) than Wal-Marts (zero), and more canoe and fishing outfitters (27) than, well, anything else. 

(Courtesy ShakataGaNai/Wikimedia Commons)

Cloverdale, Calif. (Winner 2010): Some 90 miles north of San Francisco, Cloverdale is ground zero for Sonoma County's highly regarded Zinfandels. 

(Melissa Barnes)

Brevard, N.C. (Winner 2010): Set in the Blue Ridge Mountains 45 minutes south of Asheville, this redbrick town is an outpost of authentic Appalachia. 

(Andre Jenny/Alamy)

Saugatuck, Mich. (Winner 2010): Time seems to have stood still in this lake town, where arts-and-crafts homes, picket fences, and Upper Midwest charm are still the order of the day. 

(Sally Ryan)

Kennett Square, Pa. (Winner 2010): In this prototypical American town 38 miles west of Philadelphia, tradition is taken seriously—and everyone roots for the home team. .

(Michael Mohr)

Bandon, Ore. (Winner 2010): Bandon is the rare small town that qualifies as a full-blown foodie destination, thanks to a long-growing season and chefs who get their hands dirty. .

(Stock Connectiton Blue/Alamy)

Cuero, Tex. (Winner 2010): Old West meets modern art in this small town an hour and a half south of Austin. Locals come to reconnect with their roots amid 19th-century storefronts, yucca plants, and BBQ joints—all while enjoying the great music-and-arts scene. 

(Courtesy 2008 Larry D. Moore/Wikimedia Commons)

Nyack, N.Y. (Winner 2010): Nyack is one of the most artistic towns in the Hudson River Valley. There's no shortage of antiques shops, galleries, restaurants, and charming B&Bs. 

(Michael Mohr)

Medicine Park, Okla. (Winner 2010): Built as a planned resort for overheated Okies, this charming town is a patchwork of manicured lawns, arched footbridges, and red cobblestoned lanes. 

(Joel Zatz/Alamy)

Egg Harbor, Wis. (Winner 2010): Surrounded by more than 300 miles of hidden coves and pocket beaches on Lake Michigan, Egg Harbor has been a refuge for residents of Milwaukee and Chicago for years. 

(Courtesy Royalbroil/Wikimedia Commons)

Cayucos, Calif. (Winner 2009): About halfway between San Francisco and L.A., Cayucos is everything you want in a mellow beach town—serious waves and serious food. 

(Courtesy San Luis Obispo County Visitors & Conventions Bureau/Wikimedia Commons)

Lexington, Va. (Winner 2009): This 19th-century hamlet between the Blue Ridge and Allegheny mountains looks like it came straight out of a Norman Rockwell painting. 

(Nathan Beck)

Breaux Bridge, La. (Winner 2009): In the world's crawfish capital, an hour southwest of Baton Rouge, days revolve around Cajun meals and music. 

(Courtesy Ken Lund/Wikimedia Commons)

Tubac, Ariz. (Winner 2009): Over the years, everyone from Spanish missionaries to maverick cowboys has called this high-desert town home. These days, you're most likely to find artists roaming the streets. 

(Jess Topping/The New York Times/Redux)

Wallace, Idaho (Winner 2009): Every single building in Wallace is on the National Register of Historic Places. 

(Courtesy Mandy/Wikimedia Commons)

Saugerties, N.Y. (Winner 2009): Home to three independent bookstores like Our Bookshop, pictured, Saugerties calls itself "the book capital of the Hudson Valley." 

(Brad DeCecco)

Mt. Vernon, Iowa (Winner 2009): As seen in artist Mark Benesh's version of American Gothic on a barn outside of Mt. Vernon, art isn't just confined to gallery walls. 

(Sandy Dyas)

Jacksonville, Ore. (Winner 2009): Once a gold-rush town, Jacksonville now thrives off of liquid gold—a peaceful oasis from the tourist whirl of Napa. Sample the goods at a tasting on Quady North's patio, with free seasonal fruit and cheese, shown here. 

(John Clark)

Rockland, Maine (Winner 2009): With a Japanese-born sushi chef and a Perry Ellis–trained boutique owner, Rockland has just enough sophistication to balance out the saltiness of Maine. 

(Courtesy Hannahjones/Wikimedia Commons)

Whitefish, Mont. (Winner 2009): Both folksy and stylish, Whitefish is the perfect place for ski bums and urban refugees to congregate. 

(Courtesy WikiCapa/Wikimedia Commons)

Port Jervis, N.Y. (Winner 2008): This canal hub on the Delaware River is the perfect New York oasis, full of high-art galleries and low-cost real estate. 

(Michael Mohr)

Manitou Springs, Colo. (Winner 2008): The residents, and the businesses they patronize, are very eclectic—like the Kinfolks Mountain Shop, which sells outdoor gear and is also a bar and live-music venue. 

(Richard Nowitz)

Yellow Springs, Ohio (Winner 2008): Yellow Springs is somewhere "you can breathe and feel very comfortable expressing yourself," says Kim Korkan, owner of the Winds Cafe & Bakery. 

(Jamie Holly/Wikimedia Commons)

Mazomanie, Wis. (Winner 2008): Mazo, as the locals call it, is chockablock with artists thanks to affordable rent and a co-op started in 2006. 

(Courtesy Freekee/Wikimedia Commons)

Point Reyes Station, Calif. (Winner 2008): Between the beautiful scenery, active food scene, and Point Reyes National Seashore, it's amazing we all don't spend our lives as resident Laurie Manarik did: "figuring out how to spend the rest of my life here." 

(Courtesy Edward Betts/Wikimedia Commons)

Belfast, Maine (Winner 2008): Resident Bob Hansen is amazed at the influx of artists who have moved to Belfast in the last few years: "Not just people with paintbrushes—there are jewelry makers, glassblowers, and weavers." 

(Andre Jenny/Alamy)

Catskill, N.Y. (Winner 2008): Affordable homes and beautiful landscapes provide for a healthy artist community, which supports institutions like the 1920s community theater on Main Street, shown here.

(Michael Mohr)

Truth or Consequences, N.M. (Winner 2008): T or C, as residents call it, still capitalizes on its quirky 1950 name change. Resident Susan Morrongiello Koenick came for the name and stayed for the culture. 

(Lightworks Media/Alamy)

Livingston, Mont. (Winner 2008): With its cheap rent, views of the Rockies, and Yellowstone only an hour away, Livingston is home to a lot of "young people living the good life."

(Walter Bibikow/Age Fotostock)

White River Junction, Vt. (Winner 2008): White River Junction reinvented itself into an artists' colony several years ago, supporting quirky new businesses like the Main Street Museum and the Center for Cartoon Studies.

(Courtesy Mickmaguire/Wikimedia Commons)

Millerton, N.Y. (Winner 2007): The Irving Farm Coffee House, pictured here, is a prime example of Millerton residents' preference for independent businesses over chain stores.

(Lauren Keenan)

Millford, Pa. (Winner 2007): Millford is host to a large collection of Victorian houses, the most prominent of which is the newly refurbished Hotel Fachere, shown here, where you can peacefully rock your days away.

(Lauren Keenan)

Yachats, Ore. (Winner 2007): Considering the awe-inspiring scenery and a deli like Grand Occasions, where you can take it all in with a slice of seasonal pie, you may want to move to Oregon, too.

Waitsburg, Wash. (Winner 2007): The Whoopemup Hollow Cafe, shown here, is just one delicious asset in Waitsburg's culinary arsenal.

(Ioyal Baker)

Paia, Hawaii (Winner 2007): Chic shops and small hotels like the six-bedroom Kuau Inn make Paia the Mauians' getaway spot in Hawaii.

(Douglas Peebles)

Parkville, Mo. (Winner 2007): Though bustling Kansas City is only 10 miles away, Parkville offers some healthy reminders to slow down, such as the Park University clock tower, shown here. .

(Courtesy Edit32/Wikimedia Commons)

Silver City, N.M. (Winner 2007): These historic buildings sport motifs inspired by Indian designs at Bullard Street.

(Marek Zuk/Alamy)

Petersborough, N.H. (Winner 2007): With the country's oldest art retreat, Petersborough hosts "a cool blend of artists and regular folks," who can congregate at Harlow's Pub, pictured here.

(Pamela Gleeson)

Tuscumbia, Ala. (Winner 2007): Flooring-and-plastics millionaire Harvey Robbins bought up several buildings in Tuscumbia in order to save his hometown, which is now host to thriving small businesses and artists.

(The Protected Art Archive/Alamy)

Collinsville, Conn. (Winner 2007): With the largest kayak-and-canoe supplier in New England, and a zip line across the pictured LaSalle Market & Deli, Collinsville "has been attracting more and more young people," says college student Scott Juhl.

(Christopher Percy Collier)

Barnard, Vt. (Winner 2006): Communal cooking at the Barnard General Store, pictured here, is just one of the foodie-friendly stops in Barnard.

(Morgan & Owens)

Murphys, Calif. (Winner 2006): While gold was the draw of Murphys's original inhabitants back in the 1880s, "people here are mostly concerned with friendships and community" these days, explains Jennifer Wren Stoicheff, founder of Alchemy Market and Wine Bar.

(Jonothan Sprague)

Homer, Alaska (Winner 2006): Resident Will Shlein believes those who live in the town "feel the special energy of the people and the earth" here in Homer, which is known as the Cosmic Hamlet by the Sea.

(Courtesy Keith Parker/Wikimedia Commons)

Bisbee, Ariz. (Winner 2006): With its unique inhabitants and stylish amenities, quirky and culture are both at home here in downtown Bisbee.

(Duncan Stewart)

Fayetteville, W.Va. (Winner 2006): From white-water rafting to mountain biking, Fayetteville serves as a launch site for all kinds of adrenaline junkies.

(Oliver Gerhard/Alamy)

Hudson, N.Y. (Winner 2006): Hudson's Ex-Manhattanites have found a cultured haven away from the hustle, with plenty of yoga, antiques shops, and spots like Hudson Wine Merchants, pictured here.

(Robert Wright)

Great Barrington, Mass. (Winner 2006): With a supportive and active community, Great Barrington is the kind of small town that brings out the can-do in its residents. Says local Rachel Fletcher: "You can really get involved without having to write a check. Everyone here—from old-timers to new arrivals—really takes care of the town."

(Morgan & Owens)

Rocheport, Mo. (Winner 2006): Rocheport was revitalized when a stretch of the Katy Railroad was converted into 225 miles of hiking trails. With 350,000 hikers now passing through every year, a healthy community of B&Bs and bistros began to emerge.

(Courtesy Missouri Division of Tourism)

Marfa, Tex. (Winner 2006): With the Chianti Foundation as a centerpiece to a thriving art scene, Marfa is a huge draw for the greater art world.

(Courtesy Paul Joseph/Wikimedia Commons)

Hood River, Ore. (Winner 2006): With Oregon-raised beef and Oregon-grown produce coming in, "think locally" could be a town motto. 

(Justin Bailie)
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