When it comes to quaint you might be picturing an idyllic English borough or a half timbered French enclave but the U.S. has endless charming hideaways to discover. From coastal, windswept fishing villages to mountain enclaves, here are 10 of the quaintest towns in America.
1. Stowe, Vermont
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.
Have a sweet tooth? The Ben & Jerry’s Ice Cream Factory is nearby in Waterbury. Be sure to book a maple syrup tasting at one of the local sugar farms to get a real sense of Vermont’s long and storied maple sugaring industry.
2. Breaux Bridge, Louisiana
Enjoy the quaint yet lively Breaux Bridge. Known as the Crawfish Capital of the World, the small town of Breaux Bridge offers rich history, world-class restaurants, and a very lively Cajun and Zydeco music and art industry.
Breaux Bridge is also home to the world-famous Breaux Bridge Crawfish Festival which is celebrated every May (May 5-7, 2023). This is to pay homage to the sea creature that brought fame and wealth to the town.
Aside from being a popular stopover, you might also want to stay in the quaint town for a couple of days.
3. Woods Hole, Massachusetts
The quaint New England village of Woods Hole lies at the far southwestern tip of Cape Cod with Buzzards Bay to its west and Vineyard Sound to its east. Because of its excellent harbor, Woods Hole became a center for whaling, shipping, and fishing prior to its dominance today by tourism and marine research.
Woods Hole is a small village and is easily strolled. The village is a world center for marine, biomedical, and environmental science. It houses two large, private organizations: the Marine Biological Laboratory and the Woods Hole Oceanographic Institution. A total of 49 Nobel Laureates have taught, taken courses, or done research at the Marine Biological Laboratory.
4. Helen, Georgia
When you think of wine country and the North Georgia mountains, one place naturally comes to mind: Helen, the quaintist little town in the Peach State. Turning onto the main drag is like apparating from the Deep South to the German Alps in two seconds flat. The street is lined with chocolatiers, biergartens, and souvenir shops that’ll have you thinking you’re in Europe. Outside town are a handful of wineries where visitors learn that Georgia Wine isn’t just a nice way of saying moonshine. It’s also set right on the Chattahoochee River which means plenty of rafting, fishing, and hiking. If you can’t make it in the summer, Oktoberfest here is, unsurprisingly, quite the event.
5. Woodstock, New York
To assume that Woodstock is only notable for its namesake 1969 music festival would be a major blunder—the festivities weren’t even held within city limits. In reality, Woodstock is a quaint little Catskills oasis where residents prop up an art, religion, music, and theater scene worthy of national attention. The Woodstock Byrdcliffe Guild continues to attract artists hoping to retreat from city life and hone their craft and visitors can tour the grounds and see where magic was made.
At the Maverick, a barn-like concert hall that’s still in operation today, locals have been enjoying outdoor hippie music festivals since the dawn of the 20th century and in the summer the city hosts outdoor concerts at the Village Green for all to enjoy.
When you’re ready for a dose of nature, make your way to the Overlook Mountain Wild Forest—the 4.6-mile mountain trail begins beside the monastery and runs along ruins of a never-completed hotel, a historic fire tower, and stunning viewpoints of the Hudson Valley.
5. Medora, North Dakota
One would think getting Broadway-quality performers to spend their summers in the middle of nowhere, North Dakota would be tough. But it’s barely a chore when you’re drawing them to quaint Medora, home of the Medora Musical and gateway to Theodore Roosevelt National Park.
The once-depressed cattle town was brought back to life when businessman Harold Shafer sunk millions into it turning it into an Old West Revival that avoids being too campy. Saloons and steakhouses offer stellar food; day hikes along the Pancratz Trail, just outside the Badlands Motel offer sweeping views; and a trip to the Burning Hills Amphitheater—a sort of Hollywood Bowl in the Badlands—is a must for musicals and steak-on-a-pitchfork dinner. The entire town obliterates expectations of what one would expect to find in North Dakota.
6. Jacksonville, Oregon
Life slows a pace or two in quaint, historic Jacksonville. Steeped in history, the entire town of Jacksonville is designated a National Historic Landmark. Explore the roots of the area from the days of the 1850’s gold rush to now through a variety of historical tour options including a self guided walking tour as well as trolley and haunted history tours. A quintessential western town, you’ll find yourself enthralled in how things used to be.
Jacksonville will charm you with more than its history. The quaint brick and wooden buildings are alive with great food, unique merchandise, live music, and wine as they now house an eclectic mix of independently owned shops, restaurants, spas, and lodging.
For culture seekers the Britt Festival offers a wide range of musical performances from June through September and keeps Jacksonville abuzz in the summer months.
7. Bay St. Louis, Mississippi
Considered a place apart, this quaint seaside town has been named one of the Coolest Small Towns in America by Budget Travel and was also recognized as a top 10 small beach town by Coastal Living Magazine. From friendly folks to historic buildings, this unique city embraces the heritage of the Coastal Mississippi region.
The town’s prime spot on the Mississippi Sound, an embayment of the Gulf of Mexico, provides a glorious stretch of white-sanded beach with virtually no crowds.
Just off of Beach Boulevard, you’ll find Old Town Bay St. Louis, a walkable area full of local shops and eateries. Spend an afternoon strolling through Old Town, browsing the beach boutiques and art galleries. Don’t miss the French Potager, an antique store and flower shop.
8. Seaside, Florida
Seaside is a quaint little coastal town in the Florida panhandle known for its sugar white sand, emerald water, mom-and-pop stores, and laid-back beach vibe. Seaside is located along a beautiful stretch of the coast midway between Destin and Panama City but has a totally different personality than those bustling hotspots. The town is acclaimed world-wide as one of the iconic examples of New Urbanism where a defined town center with shopping and dining are well within walkable distance to homes, cottages, and offices.
Green spaces and parks are prominent throughout the town as well as house fronts with inviting porches line these areas where walking paths encourage mingling with passersby instead of watching zooming cars. Less than 300 homes make up this town (many of them available as vacation rentals with kitschy beach-themed names) and all have a colorful picket fence and charm. The town’s streets end in distinctive beach pavilions providing access to the beautiful Gulf of Mexico and white sugar sand beaches.
A prominent feature in downtown Seaside is the Airstream Food Court where Silver Bullets serve up a myriad of food groups sure to please everyone’s palate in your party. This strip plays centerpiece to hungry people in search of gourmet hot dogs at Wild Bill’s Beach Dogs, Hawaiian shaved ice at Frosty Bites, and those looking for a creative take on the grilled cheese at the Meltdown on 30A.
9. Midway, Kentucky
Some of our most pleasant moments always seem to come when we stumble upon one thing while in pursuit of something else. So it was when we unexpectedly came upon the quaint, historic town of Midway. Located midway between Frankfort and Lexington, Historic Midway was the first town in Kentucky founded by a railroad.
Midway’s downtown followed the railroad’s fortunes and by the late 1960s and early 1970s, the few remaining businesses primarily served the local agricultural community.
Revitalization and rebirth began in the mid-1970s when several antique shops and galleries were established and the Midway I Village Guild was formed. In 1978, 176 buildings in Midway were placed on the National Register of Historic Places.
Now, Historic Midway once again thrives and enjoys its present reputation as one of Kentucky’s favorite spots for antiques, crafts, gifts, restaurants, and clothing. Several freight trains still make use of the active tracks running through Railroad Street, preserving Midway’s unique history and atmosphere.
Today, Midway continues to be a uniquely friendly and quaint town with a noticeable spirit. Among the cheery storefronts that line Main Street, you’ll find an array of antique shops, specialty boutiques, and restaurants with a little something for everyone.
10. La Conner, Washington
La Conner is one of those places in Washington State that people love to visit—time and time again. The reasons are many, but one that stands out is that La Conner is a quaint, historic waterfront village.
This riverfront town has a lovely setting located on the Swinomish Channel overlooking Fidalgo Island with plenty of waterfront restaurants.
Downtown La Conner has a wonderfully preserved Historic District with 27 vintage buildings from the 1860s to the early 1900s. Many of these were constructed during La Conner’s heyday in the 1890s when it was a major steamboat hub between Seattle and Bellingham.
Strolling through town, there is plenty of sidewalk art and boutique shops. There are also plenty of places to take in the views of the Swinomish Channel or garden courtyards with fountains and statues.
Continue your artsy walk around La Conner by heading to the Rainbow Bridge, a huge piece of functional art that spans the Swinomish Channel connecting Fidalgo Island to La Conner.
I say half your life is spent trying to get out of a small town and the other half trying to get back to one.