Bucket List July 28, 2021
These 25 Charming Small Towns Are Some Of The Coolest In America
America is a country that’s comprised of 50 wonderful, wholly unique states — each with its own identity, culture, and history. Within each state, there are big cities and small towns, and it’s these different locales that form the fabric of the United States of America. While there’s a lot to be said for America’s major metropolises and their attractions, today we’re celebrating the small towns that really capture the spirit of what makes our country so very wonderful. These small towns are places that honor history while also moving forward, where local businesses are lauded and supported, where residents enjoy an amazing quality of life and have a tremendous sense of pride in where they live. These 25 charming small towns are some of the coolest in America, offering visitors beauty, history, and experiences that will undoubtedly further your love for our great country.
During these uncertain times, please keep safety in mind and consider adding destinations to your bucket list to visit at a later date.
Northeast United StatesKennebunkport, Maine
Kennebunkport, ME 04046, USA
It simply doesn't get more quintessentially East Coast than Kennebunkport, Maine. This unassuming beach town is all weather-worn boats and craggy coastlines, whitewashed homes and unpretentious sea shacks. (The lobster rolls from The Clam Shack are particularly noteworthy, and really a must-try for any self-described foodie.) Kennebunkport has been lauded as
one of the best places to live on the East Coast
, and after visiting, you might just want to drop everything and move to this charming small town, too.
Located in northern Vermont, Stowe is a mountain town that's a picture-perfect slice of pastoral living. During the spring and summer months, visitors can enjoy outdoor activities like hiking and biking; in the winter, the skiing in Stowe is positively perfect. Of course, Stowe's beauty really shines in the autumn, as its streets and landscape come alive in bright crimson, gold, and orange hues. With so much natural beauty and Northeast charm,
is definitely one of the country's most beguiling little towns.
Salem may be known as the
most haunted small town in Massachusetts
, but don't let that keep you away. In the Northeast, pretty much
small town you visit is going to be incredibly old and historic, full of lore and legends. Today, Salem is working hard to shrug off centuries of baggage and superstition, embracing its history and gravitas with its vibrant and well-preserved downtown district. And they've been successful, too; Salem is one of the larger towns on our list, as it's become a place residents are proud to call home. Visit, and you'll see why.
Hudson, New York
Hudson is just two hours from New York City by train, but it feels as though it's an entire world away. Hudson, New York, is a charming,
-movie-level locale that has everything you could possibly want in a small town: a walkable city center, wonderful shopping and dining, and interesting, wholly unique experiences. The town was once a 1700s whaling port; today, Hudson features myriad historic buildings and antique dealers, along with fantastic shops and restaurants. To cap off your experience, a night at the historic Hudson Valley
is a must.
New Castle, Delaware
New Castle, DE 19720, USA
Overlooking the Delaware River,
is a historic, cobblestone-clad city that's as charming as it gets. The town has an incredible historical district, with destinations like Immanuel on the Green, the Amstel House, and the Old Library Museum all must-visits for history buffs. Your historical foray will continue in the downtown district, where old pubs and taverns can be found at each and every corner of the street. But it's not
history lessons in New Castle; Battery Park is a beautiful natural oasis that offers iconic New England vistas sure to leave you swooning.
If you're looking to explore one of the most historic small towns in America, definitely head to
. This charming town is known for many things, from top-rated colleges and nationally acclaimed festivals to incredible dining and breathtaking scenery. But it's Lexington's history that really defines this city. Civil War historians will find much to discover in Lexington: Stonewall Jackson's house, his gravesite, and the Robert E. Lee Chapel and Museum are all located within just a few-mile radius of one another in the downtown area of Lexington. For a living history lesson in one of the most charming small towns in America, visit Lexington.
Southern United StatesBeaufort, South Carolina
Hilton Head Island and Charleston might get all the buzz when it comes to the South Carolina Lowcountry, but the state has plenty of winsome small towns worth visiting. Beaufort is at the top of the list. This is your
quintessential Southern town
: streets lined with live oaks and Spanish moss; big, beautiful historic buildings and architecture; and lots of scenic marshes and shoreline. Walk along the beach at Hunting Island State Park, and try some fresh seafood at a local restaurant -- with a sweet tea, of course. Take a tour to learn about Beaufort's history and Gullah culture with a visit to the recently established Reconstruction Era National Historical Park. There is simply so much to see and do in this South Carolina town, a place that's positively bursting with Southern heart and soul.
St. Augustine, Florida
St. Augustine often gets overshadowed by Florida's big names like Miami and Orlando, but this town really does deserve your attention. The epitome of
, St. Augustine is a place of fascinating history and culture. Dating back 450 years, St. Augustine is one of the country's oldest and most historic cities, and places like Castillo de San Marcos National Monument celebrate its legacy. But the town is more than just historical sites and museums; its downtown district along Aviles Street -- the oldest street in the country, in fact -- has amazing local shops, incredible restaurants, and top-rated distilleries, making for a wholly delightful experience.
Mooresville, AL 35649, USA
Located in Limestone County, Alabama, Mooresville is small in size and stature, but big on history and culture. Covering just 64 acres, Mooresville has just 60 residents, but it is easily the state's coolest small town. Established in 1818, Mooresville is one of
Alabama's oldest towns
, and the entire city is listed on the National Register of Historic Places. Among these historic sites are several old homes, a post office, a beautiful church, and an inn and tavern, all of which you'll see when wandering through this delightful small town in Alabama.
Eureka Springs, Arkansas
Arkansas is an incredibly beautiful place, and
possesses everything that's so wonderful about the Natural State. This town of less than 2,000 has it all: historic sites, amazing Victorian architecture, a quaint downtown district, and spectacular scenic beauty. In fact, Eureka Springs is right in the heart of one of the most picturesque places in the country: the Ozarks. This region is well-known for its natural springs, glorious waterfalls, pristine lakes, and wondrous caves, all of which make for outstanding outdoor recreation. The town was named after its "healing" waters from the nearby natural springs, and it absolutely is a place that will make your soul happy.
Gatlinburg, TN 37738, USA
Known as the "Gateway to the Great Smoky Mountains National Park," Gatlinburg is one of the most naturally beautiful places in the entire country. Offering unrivaled views of the 520,000-acre park, Gatlinburg is a splendid place to visit no matter the season. In fact, this town of just 4,000 boasts enough arts, culture, and outdoor recreation to keep visitors very, very busy. In
, you can enjoy the only ski resort in the state, walk across the longest pedestrian sky bridge in North America, hike in the majestic Smokies, enjoy a vaudeville show, ride a cable car to see unrivaled aerial views, explore numerous museums, taste a variety of incredible cuisines, peruse myriad art galleries, or simply stroll down the street and take in the vibe of this charming, rustic town. (We're kind of partial to that last activity.)
Deep in the Bluegrass State, there is a place that's known far and wide as one of the best small towns in the country. Bardstown is a popular spot for locals and visitors alike who have an interest in bourbon, American history, incredible outdoor adventure, and a taste of charming, small-town life. Visit Bardstown and check out the nearby
Kentucky Bourbon Trail
, or explore the iconic My Old Kentucky Home State Park. Or simply sit back and tour the town on an old-fashioned
. Whatever you do, you'll be enchanted by this lovely little Kentucky town.
Midwest United StatesMarietta, Ohio
The oldest town in Ohio,
hails from 1788, predating Ohio's statehood, in fact. Nestled at the confluence of the Muskingum and Ohio Rivers, this quaint river town is full of history, culture, and breathtaking scenery. It's a place with a proud, thriving community; Marietta's downtown district is home to numerous local retailers and restaurants and is a wonderful place to wander and explore. The town is also home to Marietta College, a private university with gorgeous architecture and incredible history all its own. One of the most iconic buildings in Marietta is The Castle, which was built in 1855 and has been home to some of the town's most prominent families. This striking structure is historic, intriguing, and dashingly beautiful -- which sums up this charming Ohio town, too.
Mackinac Island, Michigan
Mackinac Island, MI 49757, USA
Mackinac Island is one of the most charming places in the country, period. Located on Michigan's Upper Peninsula, Mackinac Island is a delightful little coastal locale that enjoys a laid-back, old-fashioned way of life. In this
, you'll find residents and visitors walking, biking, and even enjoying horse-drawn carriage rides around town, making for an incredibly endearing experience and welcome reprieve from the rest of the world. While you're there, be sure to tour historic sites such as Fort Mackinac, dine at beloved eateries like The Carriage House, and sample some world-famous Mackinac Island fudge from any of the town's
Grand Marias, Minnesota
Grand Marais, MN 55604, USA
In the Land of 10,000 Lakes, it can be hard to stand out. But when it comes to the ultimate lake town experience in Minnesota,
most certainly shines. Located at the tip of northern Minnesota on Lake Superior, Grand Marais is an utterly charming little town filled with unique shops, good eats, scenic lake views, and thrilling outdoor adventures. Visit in the winter, and you'll enjoy amazing skiing. In the summer, there's nothing better than life on the lake. And in the autumn, the fall colors in this glorious little Minnesota town will absolutely take your breath away.
Known for its Dutch culture and postcard-perfect downtown, Pella is one of the most
delightful small towns in the country
. Located less than an hour from Des Moines, Pella is a small town that feels like entering another time and place -- and
. Founded by immigrants from Holland in 1847, Pella is a place that celebrates its Netherlands culture and heritage. Evidence of this is easy to see in Downtown Pella, which features Dutch-inspired architecture and several iconic windmills, such as the Vermeer Windmill, along with numerous Dutch bakeries and shops. Each spring, this small town comes alive in color, with its annual Tulip Festival attracting visitors from all across the Midwest, who come to experience the simple joy of beautiful blooms and exuberant Dutch culture.
Southwest United StatesMarfa, Texas
This tiny desert town has become a haven for the arts, with the iconic Prada Marfa making a stunning statement along U.S. Highway 90. This town of under 2,000 residents was founded in the 1880s and originally served as a railroad water stop before becoming a training facility for thousands of pilots during WWII. Today,
is unlike any other town in Texas; it's a hub for minimalist and experimental art and attracts both tourists and artists from all over the country to experience or contribute to the scene. This Texas iconoclast is wholly unique and completely wonderful.
In Arizona, the Grand Canyon tends to steal the spotlight, but two hours from this natural wonder, you'll find a small town that really is an Arizona treasure. Sedona is a small desert town surrounded by incredible red rock formations and stunning geological wonders, making it a perfect, less-crowded destination for outdoorsy travelers and adventurers. The town itself is filled with galleries, boutiques, restaurants, and attractions, including the iconic Tlaquepaque Arts & Shopping Village, which features handcrafted artisanal products and wares, as well as local restaurants serving authentic Arizona cuisine. Visit and you'll see why Sedona, Arizona is the coolest,
most underrated small town in the West
Taos, New Mexico
Taos often gets overlooked by its big sibling, Santa Fe, but this New Mexico town really does deserve your attention. While Santa Fe is often touted as the oldest town in New Mexico, the title
actually belongs to Taos
, as the city's eponymous Taos Pueblo has had residents for over 1,000 years. Indeed, it's this historic dwelling that earns Taos much of its notoriety -- it's the only living Native American community with UNESCO World Heritage Site status that's also a National Historic Landmark designation, and it’s a fascinating place to explore. Of course, Taos is more than just
attraction. The small town also has a thriving historic district that's full of restaurants, retailers, and local artisans; and the mountains and desert landscape of Taos make for incredible outdoor recreation all year-round.
If you have ever had the pleasure of visiting gorgeous Telluride, Colorado, you know that it is an absolute treasure of a small town. While this is common knowledge to Coloradans, Telluride recently earned a national nod from Travel + Leisure's coveted
Best Small Towns in America
list. In addition to its sublime scenic beauty, Telluride is also incredibly historic, and that history is a celebrated part of its culture. Downtown Telluride is a designated National Historic Landmark District with Victorian-era buildings, many of which have been painstakingly preserved and renovated to house local businesses and restaurants. And, of course, with regard to Telluride's outdoor recreation -- it's world-class. The town is well-known for incredible skiing at Telluride Ski Resort; and in the off-season, visitors can enjoy biking, hiking, fly fishing, golfing, and an abundance of river recreation.
Carmel-by-the-Sea, Carmel-By-The-Sea, CA 93923, USA
Carmel-by-the-Sea is quite possibly the most charming
in the country. This California gem is located on the Monterey Peninsula and is about as postcard-perfect as it gets. This quaint little village has lots of local restaurants, wine bars, and fairy tale accommodations that all add to its allure. Of course, the town's sublime surroundings contribute to that feeling, too. After a day of shopping and wine tasting, head down to the eponymous Carmel Beach to take in the sweeping coastal scenery and bask in a beautiful California sunset.
Northwest United StatesWhitefish, Montana
Located in the Montana Rocky Mountains, Whitefish is an outdoor adventurer's paradise with the soul of a small town. This charming town is situated near Glacier National Park, so it's the perfect home base for those wanting to explore the area's glaciers, lakes, meadows, and mountains. Whitefish Mountain Resort offers 3,000 acres of skiable terrain, and during the summer, visitors can hike, bike, zip line, and race down the mountain on an alpine slide. Back in town, Whitefish is not lacking in personality; its streets are filled with local shops, quaint restaurants, and cozy little accommodations, all of which are at their peak beauty in the winter. Whitefish gets around 300 inches of snowfall each year, and seeing the downtown covered in a blanket of white will make you feel as though you're in a
real-life snow globe
Jackson Hole, Wyoming
Jackson Hole, Wyoming 83001, USA
The rough and rugged beauty of Wyoming cannot be overstated. Jackson Hole is best-known as a winter wonderland, with the city seeing over 400 inches of annual snowfall. A playground for outdoor enthusiasts, visitors come to ski and snowboard on Jackson Hole's 2,500 acres of skiable terrain. But it's more than just a top ski spot; visitors return to this Wyoming valley year after year for its picturesque scenery and distinct small-town sensibility. This is epitomized with Jackson Hole's annual
, which include delightful displays, festive lights, and an ice rink located right in the middle of town!
Cannon Beach, Oregon
This town on the Oregon Coast is one of the
, charming places you'll ever visit, and it captures the wonder of the Pacific Northwest. Cannon Beach is defined by its shoreline, which features the iconic and commanding Haystack Rock. This unique formation is made up of basalt created by lava that flowed through Oregon 16 million years ago. Its beaches are spectacular, too, and when you've tired of a day on the water, head into town to enjoy the freshest, most flavorful seafood of your life.
Friday Harbor, Washington
Friday Harbor, WA 98250, USA
Lauded as one of the
most beautiful towns in America
, Washington's Friday Harbor is a vision. The town is located on San Juan Island, one of the most naturally stunning places in the country. Friday Harbor is a quintessential PNW seaside town, with winsome boats, lighthouses, and docks dotting its shores. Sailing and kayaking are popular pastimes here, and visitors will delight in whale watching along the Pacific shores, too. In town, an abundance of delightful shops and restaurants await, offering visitors a true taste of the Pacific Northwest.
Big cities may get all the attention, but it’s America’s small towns where the magic really happens. Visit these cool little towns, and you’ll agree that they are truly some of the best places in America — and absolute bucket-list musts.
For more bucket-list-worthy adventures across America, you’ll definitely want to visit these
lesser-visited national parks. Address: Sedona, AZ 86336, USA Address: Telluride, CO 81435, USA Address: Hudson, NY 12534, USA Address: Carmel-by-the-Sea, Carmel-By-The-Sea, CA 93923, USA Address: Beaufort, SC, USA Address: Kennebunkport, ME 04046, USA Address: Grand Marais, MN 55604, USA Address: Mackinac Island, MI 49757, USA Address: Whitefish, MT 59937, USA Address: St. Augustine, FL, USA Address: Lexington, VA 24450, USA Address: Bardstown, KY 40004, USA Address: Stowe, VT 05672, USA Address: Jackson Hole, Wyoming 83001, USA Address: Cannon Beach, OR, USA Address: Taos, NM 87571, USA Address: Gatlinburg, TN 37738, USA Address: Mooresville, AL 35649, USA Address: Eureka Springs, AR, USA Address: New Castle, DE 19720, USA Address: Marietta, OH 45750, USA Address: Marfa, TX 79843, USA Address: Friday Harbor, WA 98250, USA Address: Pella, IA 50219, USA Address: Salem, MA, USA