10 Small Towns With Big Personalities

Quirky and irresistible

Photo: Lars Plougmann/flickr

Revitalized Main Streets, new industries, an increase of remote/online employment opportunities: People who want to leave the big city behind now have more practical reasons to opt for a small-town lifestyle. "Small," of course, is a relative term. Fodor’s limits the towns on its "Best Small Towns" list to populations of 30,000 or less, while other outlets bump their maximum size up to 100,000.

Rather than head counts, however, small towns are often defined by characteristics like a slower pace of life, family-oriented events, walkability, proximity to nature and an authenticity that's not evident in larger places. Not only are more people choosing to move to these undersized enclaves, more travelers are coming as well. Some small towns have developed unique personalities that give them a cosmopolitan or offbeat feel.

Here are some small towns that travelers and big-city transplants have embraced because of their oversized personalities.

Bisbee, Arizona

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Bisbee is in southernmost Arizona, about 100 miles from Tucson in Cochise County (the same county as the famous town of Tombstone). It's had a tumultuous history involving boom-and-bust mining businesses and violently suppressed labor strikes. The surrounding Mule Mountains, the frozen-in-time Old Town streets, antique shops and a vibrant arts scene have given this Southwest enclave new life as a tourist destination.

The town began offering tours of its mine in the 1970s, but tourism really took off in the 1990s when Bisbee began embracing an unusual mix of businesses without changing its Victorian-era architecture. Now, boutiques, eateries, hotels and art galleries compete for tourists’ attention along with the outdoor activities in the surrounding mountains. Once known for its rowdy saloons, Bisbee still has a happening nightlife scene, which is surprising, given that its population is only about 5,000.

Marfa, Texas

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Marfa was founded as a water stop for steam trains traveling on a southern Texas railroad. Despite its remote location, the town has always had an artistic, literary streak. Legend has it that the wife of the railroad’s chief engineer chose the name Marfa after reading about a housekeeper with that name in Dostoevsky's "The Brothers Karamazov." Sitting on a high (4,000 feet), arid plateau between different mountain ranges, Marfa has a kind of stark beauty. Once only known for the "Marfa lights" or "ghost lights" that still appear mysteriously on the horizon, this town has become an unexpected attraction for creative types.

Minimalist artist Donald Judd left New York City, which he found overly pretentious, in the 1970s and established himself in Marfa. Other artists followed, creating a vibrant scene that includes galleries, offbeat installations like a Prada Store in the middle of the desert outside of town, and a small-city-sized selection of bars, music venues and restaurants. Marfa Myths, a springtime music festival, is hosted in the historic Ballroom Marfa and in other venues throughout this town of 2,000.

Ashland, Oregon

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Ashland is a college town in southern Oregon with about 20,000 residents. It has been called one of the top small arts towns in the world. This is due, in part, to its extremely popular summertime theater season. The Oregon Shakespeare Festival features around a dozen different plays in three theaters, with the classically designed outdoor Allen Elizabethan Theatre the undisputed top attraction.

Ashland also hosts an independent film festival, a monthly art crawl, concerts and a seasonal artisans’ market near the impressive 100-acre Lithia Park. Coffee shops, boutiques, antique emporiums, wine bars and brewpubs dominate the historic Main Street area of the city, while mountains, bike trails and rivers give outdoors enthusiasts something to do as well. The city claims more than 100 eateries and hosts a number of food-related events, including the Ashland Culinary Festival.

Stuart, Florida

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The population of this small Atlantic Coast town approaches 20,000. Stuart is built on a peninsula, so it has an abundance of shoreline and beaches despite its diminutive size. The historic downtown area, waterfront and prevalence of independent businesses make this a charmingly unique town. Activities in Stuart include deep sea fishing, snorkeling at nearby Bathtub Reef, taking a wildlife tour and visiting the aquariums at the Florida Oceanographic Coastal Center.

Stuart owes its personality to local efforts to keep growth in check. Other similarly attractive towns have become dominated by seaside condo developments and hotels, but this one has, thus far, escaped that fate. The tallest building inside Stuart is six stories, and independent businesses dominate the town and its lengthy boardwalk.

Grand Marais, Minnesota

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Grand Marais has about 1,300 residents, but it has earned praise from some of the country’s biggest travel publications. Budget Travel once called it the "coolest small town in America," Outside named it a top beach destination and National Geographic Adventure dubbed it the Next Great Adventure Town. Lake Superior might be too chilly for swimming, but it offers fishing, sailing and kayaking, and the nearby highlands have alpine skiing in the winter and mountain biking, hiking and climbing in the summer.

The town itself is arranged around the harbor and features independently owned restaurants, a popular co-op, cafes, bars, music venues and art galleries. A number of artists have set up shop in town, and if you feel inspired, you may be able to indulge your own creative side at the North House Folk School, which offers classes in woodworking and other traditional skills. Music events, such as the three-day Radio Waves Music Festival, are on the calendar as well.

Clarksdale, Mississippi

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Clarksdale, a town of about 20,000 in northwestern Mississippi, was the birthplace of some of the world’s most famous blues musicians. Muddy Waters, John Lee Hooker and Ike Turner came from this small town, as did soul music legend Sam Cooke. When the New York Times visited a decade ago, they found a modest place that had embraced its musical history and created a modern scene that paid tribute to the past but also kept one foot in the present.

Actor Morgan Freeman is part owner of the town’s top blues club, Ground Zero, and he used to have a hand in other properties, including a fine dining restaurant. Local and regional acts play Ground Zero and other venues around town while Clarksdale’s past musical luminaries are celebrated at the Delta Blues Museum, which houses Waters' childhood cottage. Visitors will also notice an unusual guitar-themed street sign that marks the mythical spot where early blues master Robert Johnson supposedly sold his soul to the Devil in exchange for his prodigious guitar skills.

Paia, Maui, Hawaii

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Paia is a town of 3,000 on the island of Maui. This modest place is notable for a couple of reasons. First, it's a base for windsurfers who practice their craft at nearby Ho'okipa, one of the most sought-after windsurf spots in the world. The town is also one of the first (or last) stops on the famous Hana Highway, a scenic drive popular among tourists. Economically, Paia became a sort of boomtown thanks to the sugar industry. The original farming settlement was destroyed by a tsunami and was rebuilt in the 1940s.

Despite an influx of tourists and windsurfing enthusiasts, Paia has retained its quaint and historic mid-century atmosphere, and it remains surrounded by pineapple and sugarcane fields. The brightly colored downtown buildings now house independently owned boutiques, restaurants and art galleries. The "locally-grown" approach was in place here well before it became popular on the Mainland, so this is the perfect town to find only-on-Maui foods and goods (namely, Maui-grown coffee and local-plantation-grown fruits).

Rockland, Maine

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Rockland is a city of 7,000 in southern Maine. Its coastal location made it an important base for fishing fleets and shipbuilding in past centuries. The limestone rock formations also provided raw materials for lime production. Today, tourism has become the main business, but Rockland’s past is still on display, especially on "Maine Street," at the historic lighthouse and, of course, along the ruggedly scenic coastline.

The town has long been popular with artists as well. Art galleries and exhibit spaces abound (especially the famous Farnsworth Art Museum), and the creativity stretches beyond the canvas, with boutiques and restaurants. Each summer, Rockland hosts the Maine Lobster Festival, a carnival-like food event that showcases the Atlantic’s most famous crustacean.

Hood River, Oregon

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Hood River is a haven for outdoor sports. The consistent conditions on an especially wide section of the Columbia River have earned this Pacific Northwest town a reputation as one of the best windsurfing spots in the world. The town’s namesake, the Hood River, is a tributary of the Columbia.

Sailors, kiters, kayakers and stand-up paddleboarders can spend time on the water, while mountain bikers and hikers head inland to enjoy trails that pass waterfalls and other scenic features. Year-round skiing is only a short ride away on the Palmer Snowfield. Mount Hood Meadows also offers skiing. After hitting the slopes, trails or water, tourists can enjoy a big-city-worthy collection of eateries, wine bars and brewpubs before perusing antique shops, boutiques and art galleries.

Homer, Alaska

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The Kenai Mountains protect Homer from the severe Arctic cold (freezing temps are rare) and provide a stunning backdrop for this town of 5,000. As a tourist destination, Homer draws outdoor enthusiasts who flock here to kayak, fish, hike, climb and camp. Salmon runs, which take place at two different times during the summer, are extremely popular with anglers.

The Kenai Peninsula town has other attractions, too. Its museum, the multi-focus Pratt Museum, seems like it belongs in an urban setting, while the restaurants and an art gallery also give Homer a quaint-but-cultured feel. The town accentuates this dynamic with live music and theater performances.