The 9 Cutest Small Towns in America
Every year, America’s small towns draw tourists—and new residents—to their streets in droves. They are, after all, reminders of a simpler way of life, where mom-and-pop shops are the norm, everybody knows your name, and the pace is slower than the speed of tweets. To help you get away from the breakneck tempo of your daily routine, we rounded up nine of the cutest small towns for an easy weekend escape, from a picturesque New England coastal haven to a romantic Southern getaway that feels untouched by time.
With its local wineries and Pacific Coast Highway views, the Northern California town of Carmel-by-the-Sea is as idyllic as its name suggests. Come for the beach, a mile-long swath of white sand from which you can view dolphins and sea lions, then wander around town to shop quirky independent boutiques and see whimsical cottages that look like they came straight out of a fairytale. The atmospheric gardens and chapels at Spanish-colonial Carmel Mission, founded in 1770 and designated a National Historic Landmark, offer worthy spots for reflection, though you'll find just as much tranquility after a stay in one of the intimate suites at L'Auberge Carmel. For dinner, nab a table at Cultura Comida y Bebida, where chef Michelle Estigoy serves standout chicken tinga tacos and epazote quesadillas inspired by her family's Mexican heritage.
Accessible only by air and sea, the fishing village of Sitka is a remote beauty that anyone who has watched the 2009 Sandra Bullock film The Proposal is sure to recognize (filming took place in Rockport, Massachusetts, but sets were built to resemble this port town). Here, you can indulge in the natural pursuits Alaska is known for, from whale watching and kayaking to hiking up a dormant volcano or strolling through towering spruce trees—spotting bald eagles and totem poles along the way—at Sitka National Historic Park.
It’s easy to see why this high-desert town in the Sangre de Christo Mountains has become a haven for artists, writers, and other creative types. The UNESCO World Heritage Site is a feast for the senses thanks to its striking adobe architecture, red-rock canyons, and snow-tipped peaks. Feeling inspired? View works by the likes of Agnes Martin and other local painters at the Harwood Museum of Art and more than 80 other galleries. There are also plenty of activities to keep adrenaline junkies engaged year ‘round. Summer brings hiking and hot air ballooning, while winter offers some of the best skiing in the country.
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As art meccas go, Marfa is an unlikely one. Founded in 1883, the tiny Texas town—population under 2,000—has served as a railway headquarters and military training base, but it wasn’t until the 1970s, when artist Donald Judd moved there, that it became a cultural destination for the aesthetically informed. View some of his most iconic concrete sculptures on a sunrise tour of the Chinati Foundation, or make like the Insta glitterati and take a selfie in front of Elmgreen and Dragset’s now-famous Prada Marfa installation, off Highway 90.
If this Lowcountry fishing village looks straight out of a movie set, that’s because it is: Beaufort was the backdrop for such films as Forrest Gump and The Big Chill thanks to its sprawling antebellum mansions, moss-draped oaks, and picturesque downtown streets. Located on Port Royal Island in South Carolina’s Sea Island chain, the town makes an ideal base for enjoying simple pleasures and all manner of aquatic diversions, including paddle boarding, kayaking, dolphin watching, and crabbing.
The romantic ideal of Main Street is alive and well in this mining town on Illinois’s northwestern border—think of it as the Midwest’s version of Stars Hollow. Trolley cars still cruise down the historic lane, which is lined with 19th-century brick buildings and cute galleries, boutiques, and craft shops that give it a distinctly small-town feel. American history fanatics, however, will be more impressed with Galena’s status as the home of Civil War hero Ulysses S. Grant, a fact illuminated at the U.S. president’s namesake museum.
On the southeast tip of Martha’s Vineyard, Edgartown is the quintessential New England seaside getaway with classic shingle-style buildings, windswept dunes, and a scenic lighthouse. Though the beaches are the draw, the onetime whaling port brims with storybook charm. Tour the 18th-century homes of whaling captains on foot or bike, then try your hand at sailing like a local. All it takes is a short ferry ride to explore neighboring Chappaquiddick Island, where, during the summer, you can play a round of night golf by the light of the full moon.
This impossibly quaint Green Mountain town has all the makings of a Norman Rockwell painting—right down to the general store. But there’s more to Stowe than simple pleasures. Not only does Stowe have Vermont’s tallest peak, making it one of the East Coast’s most popular (and powder-friendly) ski destinations, it’s also home to the Trapp Family Lodge, an Austrian-style chalet owned by the family immortalized in The Sound of Music, as well as a stellar culinary scene. Don't miss the grilled cauliflower steak with quinoa at our favorite dinner spot, Plate. Have a sweet tooth? The Ben & Jerry’s Ice Cream Factory is nearby in Waterbury.
St. Augustine, FL
The cobblestone streets of St. Augustine are steeped in history. Founded in 1565 by Spanish conquistadors, the northern Atlantic coast town is studded with colonial architecture, from the 17th-century Castillo de San Marcos fortress to the Victorian antiques-filled Lightner Museum, housed in an 1887 Spanish Renaissance Revival building commissioned by Rockefeller business associate and Florida real estate magnate Henry Flagler. If sun and sand is what you seek, there’s plenty of that, too: Anastasia State Park comprises four miles of wildlife-dotted beach and maritime forests.
What to Pack on Your Next Trip
Headed on a small-town adventure this season? Don’t forget to pack some of our favorites from Everlane, Madewell, and Nordstrom.
Women’s Winter/Fall Small Town Outfit
Women’s Leather-ish Outfit for a Small Town in the Winter/Fall
Men’s Oat Winter Coat
Men’s Winter Getaway Outfit Gray Blazer
Women’s Winter Outfit to Wear on Your Travels
Women’s Chill Flannel and Ripped Jeans Winter Outfit for a Stylish Traveler
Men’s Cute Winter Outfit for a Walk in the Snow
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