The 30 Most Charming Small Cities in the USA

by Paul Stafford  |  Published March 29, 2021

Beyond the bright lights of LA, Chicago and New York there are hundreds of smaller US cities doing their own thing in the realms of food, culture, sports and heritage. Here are 30 of the best small cities in USA.

Asheville during the golden hour (Photo: courtesy of

Every single town and city in USA has its own flavor. Each one presents a microcosm of community and character to the world, based on innumerable factors, with location, history and heritage all playing some of the most essential roles. When this balance of factors is just right, you get a uniquely charming place that can offer something to the visitor that’s well worth traveling for. But the United States has thousands of cities.

All 30 cities listed below received the most votes after we surveyed a broad number of professional writers, photographers and travel industry specialists. Each voter was asked to select their favorite five small cities – with a population between 10,000 and 250,000 – drawing their selection from at least three different states. According to the US Census Bureau, as of 2019, there were at least 780 cities with a population of 50,000 people or more in the country, and many more above 10,000. Naturally, many fantastic cities didn’t make the list, but amid stiff competition, here are the winners.

Ann Arbor, MI

Lovely Ann Arbor is a fitting city with which to begin our list. Home to the University of Michigan, it has long been a seat of higher education, forward-thinking, technology and progressive ideas. You can see echoes of these elements everywhere, including at the numerous annual events held in the city, including expos, airshows, and the annual film festival that has been running for decades. In the city’s lively dining scene, this same balance of tradition and modernity is reflected by Ann Arbor mainstays such as Zingerman’s Deli, right through to the trendy international cuisine from across five continents.

Annapolis Harbor (Photo: courtesy of Bob Peterson)

Annapolis, MD

Maryland state’s capital city of Annapolis is a beautiful, leafy small city. It is sprinkled around a number of creeks on the Severn River’s estuary as it pours into Chesapeake Bay. Annapolis played an integral role in the final phases of the American War of Independence: Congress sat in Maryland State House, the oldest Capitol in the US, while the city was the US capital, briefly, from 1783 to 1784. Today you can explore the colonial architecture and rich history, or take a sailing trip in the bay. Boutique shopping in Annapolis Downtown is another popular pastime here.

Ashland, OR

One of the smaller cities on this list is pretty Ashland. Particularly during the warmer months, this is an excellent base from which to explore the trails of the surrounding mountains, either by bike or hiking. Back in the city, Ashland is best known for its annual Oregon Shakespeare Festival, where hundreds of performances are held at the city’s various theatres from late February through to late October. Each season runs classics such as ‘A Midsummer Night’s Dream’ along with local and topical adaptations that repurpose the Bard’s work for contemporary audiences. Other film and theatre events take place throughout the year.

Asheville at dusk (Photo: courtesy of

Asheville, NC

Asheville is a true gem of the American South. Backdropped by the Blue Ridge Mountains, the city showcases an impressive array of architecture and culture. Not to be confused with Nashville in neighboring Tennessee, Asheville also has a vibrant music scene, which skews heavily towards street performance and folk music. Fine examples of Art Deco buildings can be found Downtown, particularly the City Hall and S&W Market, across from Asheville Music Hall. The city is also home to the huge Biltmore Estate, a Gilded Age mansion built for the Vanderbilt family. Tours of parts of the building are available.

Bellingham, WA

Tucked away in the northwest corner of the United States is the city of Bellingham, whose history is closely intertwined with the water. Bellingham was an important site for boatbuilding and fishing, with the former benefitting from a plentiful supply of lumber from forests nearby. Today, tourism is one of the mainstays of the city, with a huge waterfront redevelopment underway. But it’s the great outdoors beyond that draw most people to Bellingham. Mount Baker is an excellent ski resort in winter, while the North Cascades National Park to which it belongs is a remarkable expanse of montane wilderness.

Indiana University Bloomington (Photo: Nyttend via Wikimedia Commons)

Bloomington, IN

Bloomington is a lively Indiana city that is dominated by the sprawling Indiana University (IU) campus. The campus is home to the Eskenazi Museum of Art, along with an array of institutions dedicated to music and the arts. Wander around Downtown and the campus and you’re bound to pass one of the city’s dozens of historical buildings listed of the National Register of Historic Places, such as Bloomington City Hall. IU has produced a stellar list of alumni, including Wikipedia co-founder Jimmy Wales, author Suzanne Collins, DNA pioneer James Watson, and many more eminent individuals. Sports fans might want to look up an IU Hoosiers game while in the city.

Charleston, SC

Charleston, the name evokes images of stunning architecture and culture that fuses elements of West African, French and English sensibilities. This highlights a darker, colonial past, along with its ignominious role in the slave trade, for which the city formally apologized in 2018. But that is because the modern city is redefining itself, playing on its strengths and atoning for its weaknesses. Charleston is rich in history – some buildings date back to the late 1600s – a Gilded Age mansion, plantation tour or one of the many history museums are a great place to start. Plus, the food is remarkable, blending Charleston’s cultural influences with fresh catches straight from the North Atlantic.

Nobska Lighthouse Falmouth, MA (Photo: David Siu via Flickr / CC BY 2.0)

Falmouth, MA

When you head even further up the North Atlantic coast of the US, the cities aren’t just named after British kings, but after British towns. Falmouth, first settled in 1660, is one such place. The city retains a laid-back rural charm, along with all the classic Cape Cod tropes such as the squat, white Nobska Lighthouse, waterfront seafood shacks, quaint wineries, and pleasant sandy beaches. For nature lovers, there are numerous wildlife refuges and conservation areas with hiking and kayaking, such as Waquoit Bay. And when you’re ready to explore farther afield, Martha’s Vineyard and Nantucket islands are just a short ferry ride away.

Fredericksburg, TX

Most trips to central Texas are commandeered by the cities of San Antonio and Austin, but deep inside Texas Hill Country, Fredericksburg offers a bucolic escape tinged with German heritage. It’s also the capital of the Texan wine industry. If you’ve never heard of Texan wine before, that’s because it’s a burgeoning region that produces good Malbec and Viognier grapes. There are wineries in Fredericksburg, as well as scores more on the road east towards Austin. The Historic District offers a charming glimpse of central European colonial architecture, complete with biergartens and restaurants serving hearty German cuisine.

Grand Rapids cityscape (Photo: courtesy of Experience Grand Rapids)

Grand Rapids, MI

Grand Rapids, Michigan’s second largest city after Detroit, is one of the larger cities on this list with a population of around 200,000 (although the metropolitan area is much larger). It’s so large that it has had many nicknames. The current ‘Beer City’ moniker has stuck thanks to the numerous breweries, where beer tours are common, such as at Founders Brewing Co. and The Mitten Brewing Company. River City is another nickname for Grand Rapids. Many of the city’s best sights can be found along the leafy banks of Grand River, such as Grand Rapids Public Museum, with its history exhibits and Apollo Space Capsule. Grand Rapids Art Museum is also nearby.

Falls Park in Greenville (Photo: James Willamor via Flickr / CC BY-SA 2.0)

Greenville, SC

While there’s only an alphabetical order ascribed to our top 30, the friendly South Carolinian city of Greenville is a top contender for most charming. Falls Park on the Reedy transforms the riverscape as it runs through the city center into a stunning waterfall park, complete with pedestrian suspension bridge. But it’s the food for which Greenville is receiving most attention of late. This up-and-coming food capital of the South specializes in concocting creative Southern cuisine, such as sweet potato biscuits and boiled peanut hummus at its 100-plus downtown restaurants and the many hundreds more beyond. To the north, Paris Mountain State Park offers great outdoors activities in the Blue Ridge Mountains.

Ithaca, NY

In the heart of New York’s Finger Lakes region, and home to the Ivy League’s Cornell University, is the lovely city of Ithaca. Adding to the collegiate atmosphere here, there are excellent museums in the city dedicated to science (Sciencenter) and paleontology (Museum of the Earth). Also in Ithaca, Namgyal Monastery is the North American headquarters of the Dalai Lama. Ithaca sits at the southern tip of Cayuga Lake, and you can wander along the series of waterfalls that flow towards Cornell’s impressive campus. Together with nearby Seneca Lake, this region has proven itself excellent for growing grapes, which in turn has encouraged over 100 wineries to set up production. Many of these open their doors to visitors, and Cayuga Lake Wine Trail is an excellent day trip from Ithaca.

Knoxville’s Sunsphere (Photo: courtesy of Decross

Knoxville, TN

Knoxville was put on the global map during the World’s Fair of 1982. A lot has changed in four decades, but the event marked a turning point for the city. The 266-ft (81m) Sunsphere is a landmark remnant of the fair, with the World’s Fair Park becoming a focal point for tourism. To the west of the park is Knoxville Museum of Art, with an excellent collection of 19th-century through to contemporary regional art. To the east of the park is Downtown, where you’ll find excellent Tennessean cuisine and plenty of Appalachian culture, particularly around Market Square. True Appalachia is due south of the city with the unmissable Great Smoky Mountains National Park.

Marietta, OH

On a gentle bend of the Ohio River you’ll find Marietta, a once-strategic outpost that grew in size soon after US Independence in a bid to settle as much land as possible. The Ohio River Museum here goes into more detail and you can even ride an authentic paddle steamer upriver. But Marietta’s significance comes from its role in the lives of groups oppressed under US rule: Marietta was a station on the Underground Railroad and, somewhat sadly, it was built atop a series of Native American ceremonial mounds known as the Mariette Earthworks. Remnants can be seen around the city, such as at Mound Cemetery.

Yountvilla near Napa (Photo: Dave Dugdale via Flickr / CC BY-SA 2.0)

Napa, CA

Napa is one of the cities on this list whose name precedes it thanks to one very specific reason: wine. For some visitors to this Californian city, it is difficult to imagine doing anything other than wine-related excursions. In Napa alone, there are tasting houses and wineries on practically every corner. But there is plenty in Napa city for the history buff too; Napa got its start as a silver mining town and the Silverado Trail from Napa to Robert Louis Stevenson State Park is a great way to combine wine and mine alike. Nature lovers might wish to head down to the Napa River to look for the beavers that make it their home.

Fifth Avenue South in Naples (Photo: courtesy of

Naples, FL

Where Miami Beach attracts the flashy and ostentatious to southern Florida, Naples draws the sophisticated and curious traveler. The small city is a gateway to an exceptional array of wild spaces, including Corkscrew Swamp Sanctuary, Big Cypress Natural Preserve and Everglades National Park. If you’re looking for wildlife, you’re sure to see plenty along the various boardwalks of these conservation areas, including birds, alligators and other reptiles. Downtown Naples is well known for the upmarket shopping, as well as antiques around the open-air shopping zone known as Tin City. Naples Beach, a seven-mile stretch of white sand, is a perfect place to catch the sunset.

Newport, RI

One of the oldest colonial cities in the US is Rhode Island’s charming Newport, founded in 1639. It’s importance through the ensuing centuries is reflected in the military installations like Fort Adams, built in 1799, and the numerous Gilded Age mansions that grace the city’s tree-lined streets in the south of the city. Highlights that are now open to the public include mansions (known colloquially, and cheekily, as ‘cottages’) belonging to the Vanderbilts (Marble House), and various other wealthy industrialists. Chateau-sur-Mer and The Breakers are both fine examples. Sailing is another popular pastime in Newport, with plenty of cruises available to visitors.

Downtown Palm Springs (Photo: courtesy of

Palm Springs, CA

Sat in an arid Californian landscape, surrounded by Coachella Valley and the wider Sonoran Desert, it might not sound like Palm Springs is a place of charm and relaxation. The Native Cahuilla people called it Sec-he, which roughly translates to ‘place of boiling water’, and yet through the mysteries of US irrigation systems, there are dozens of golf courses around Palm Springs. That is because, since the late 19th century, the city began a transition from a dry backwater to the vibrant, cultural hub and resort city that you see today. Palm Springs is also popular with the LGBTQ+ community, electing the city’s first openly bisexual mayor in 2020.

Portland, ME

Central to the charm of Portland, in Maine, is its enthralling waterfront, complete with a promenade, offshore islands and still-functioning fishing wharves. There is even a narrow-gauge railway that runs trips north along the coastline. Much like its namesake on the other side of the country in Oregon, Portland in Maine has a lively theater and arts culture, the latter best showcased at the Portland Museum of Art, located at the heart of the city’s arts district. The museum’s vast and impressive collection includes works by Degas, Picasso, Magritte, Munch and Monet. To the south of downtown the craggy Fort Williams Park is dotted with historic military buildings and the 1791-built Portland Head Lighthouse.

Downtown Providence (Photo: Will Hart via Flickr / CC BY 2.0)

Providence, RI

Like many other East-coast cities on this list, Providence started life as one of the oldest European settlements in the United States. Its Puritan roots start in 1636 and the link between history and charm is palpable in many areas of the city, particularly the East Side near the Providence River, where you’ll find the Old State House (1762), the First Baptist Church in America (1638) and many other impressive old buildings, such as Fleur-de-lys Studio. Rhode Island School of Design’s Museum is well worth a visit for its excellent collection of fine art from around the world, including pieces from Andy Warhol, Monet and Picasso. You’ll also find the Ivy League’s Brown University in Providence.

Richmond, VA

Richmond’s unmissable Civil War Museum offers a glimpse into the Virginian city’s often turbulent past. Uniquely, the museum looks at the war through the eyes of the three main groups involved: African Americans, Union fighters and Confederates. As capital city of the Confederate of Virginia, and the largest city on this list (not including metropolitan areas), Richmond is the kind of city where it pays to take your time. The Capitol is one of many stunning pieces of architecture around the city. The Virginia Museum of Fine Arts is among the largest in North America, showcasing exquisite works including Fabergé eggs, artworks from the likes of Goya, Rousseau and van Gogh, and even ancient Egyptian artefacts. But perhaps the highlight is the museum dedicated to Richmond’s best-loved adopted son (literally), Edgar Allen Poe.

Music in Salem (Photo: courtesy of Jared Charney)

Salem, MA

It’s impossible for most people to disassociate Salem from witches. But the site of the infamous witch trials of 1692 has so much more to offer visitors. The Peabody Essex Museum holds a large permanent collection of Asian and American fine art. Being a major early port on the North Atlantic, there are some superb buildings at the Salem Maritime National Historic Site, as well as the Friendship of Salem, a 171-foot (52m) replica of an 18th-century trading ship. Okay, you’re probably still wondering about the witches though, and you’d be right to do so, for there are dozens of museums and colonial mansions linked to the city’s gruesome passage of history. A good place to start is a 17th-century wooden building known as The Witch House.

Santa Barbara sun (Photo: courtesy of

Santa Barbara, CA

Many cities in California feel pretty intense, sprawling for endless miles of roads and concrete. Santa Barbara is a very different place indeed, never really losing the laidback Hispanic charm that defined its early years as a Spanish settlement. The Old Mission, built in 1786, sits right beside the Museum of Natural History, which explores the diverse flora and fauna that pushes in close to the city. This is best seen in real life first at the Santa Barbara Botanic Garden, then in the wild expanse of Los Padres National Forest beyond. On the other side is the Pacific Ocean with its long stretch of palm tree-lined sand: true California dreaming.

Santa Fe (Photo: courtesy of

Santa Fe, NM

Perhaps the most unique city in the United States is Santa Fe, thanks to the preservation of its traditional, precolonial Pueblo style of architecture throughout. Known as Pueblo Revival, along with hints of Spanish colonial, common traits include adobe exteriors, exposed wooden roof beams known as vigas, and flat roofs. This style is used for most homes in the city, but among the best examples are Palace of the Governors, which contains a local history exhibition, and New Mexico Museum of Art. In fact, art is Santa Fe’s main draw, with numerous galleries and institutions dedicated to Contemporary Native American Arts (MoCNA), the pioneer of American Modernism Georgia O’Keeffe, who lived in the city, and modern art at Meow Wolf Santa Fe.

Saratoga Springs, NY

Horse racing history and spa relaxation are two main reasons why visitors find Saratoga Springs in New York to be worthy of being branded charming. The National Museum of Racing, which is near Saratoga Racetrack, is dedicated to all things thoroughbred. The annual summer meet draws top horse racers from around the country over the course of six weeks. As the name suggests, Saratoga Springs was established thanks to its natural springs, which are protected to a certain degree in Saratoga Spa State Park, although perplexingly a golf course has also been built on the site. You’ll find some great spa and bath houses here. There’s also a walking trail, passing by a small geyser.

Oak trees at Wormsloe near Savannah (Photo: Jeff Gunn via Flickr / CC BY 2.0)

Savannah, GA

Although there’s no playing favorites on this list, Savannah, Georgia’s Historic District really is the epitome of charm. Little orange trolley cars and horses pulling carriages are common in this area, taking visitors back in time. The streets, dotted with colonial mansions and other historic buildings, are lined by oak trees that drip ghostly Spanish moss. Impressive oak forests in this vein populate Wormsloe Historic Site. Savannah played an integral role in the fortunes of the Civil War’s belligerents, and many tours explore this passage of the past. And don’t miss East River Street, lined by old warehouses and a pleasant promenade, where you can spot paddle steamers and cargo ships plying the Savannah River towards the North Atlantic.

Sioux Falls park in the city center (Photo: courtesy of Experience Sioux Falls)

Sioux Falls, SD

The eponymous waterfalls of Sioux Falls take center stage in South Dakota’s most populous city. Falls Park was built around them, providing a bucolic attraction at the heart of the city. The remains of Queen Bee Mill point to the region’s original importance as an agricultural center. Today, Sioux Falls is a great destination for families, thanks to sights like the Butterfly House and Aquarium, and the Great Plains Zoo and Museum of Natural History. For outdoors enthusiasts, the Sioux Falls Bike Trail follows a 19-mile (31km) loop along the course of the Big Sioux River through Downtown and beyond.

South Lake Tahoe, CA

Lake Tahoe has long been the in-state getaway of choice for most Californians. At an elevation of around 6,000ft (1,830m), the climate is cool and clear in the summer, with excellent access from South Lake Tahoe to the Sierra Nevada Mountains, even connecting to the Pacific Crest Trail. During the winter months, the city converts into a ski resort, making the most of the great pistes of East and Monument peaks, or the Sierra-at-Tahoe skiing resort. Besides the incredible surrounding mountains, Pope and Lakeside beaches are lovely stretches of sand lapped by the pristine, clear waters of the lake.

St. Augustine, FL (Photo: Doug Anderson via Flickr / CC BY 2.0)

St. Augustine, FL

While we have plenty of historic cities on this list, none can beat Florida’s St. Augustine to the title of being the oldest continuously inhabited colonial settlement in the United States. That’s because Spanish Conquistadores established the city way back in 1565. Make directly for the Colonial Quarter where you will find St. Augustine’s oldest and most charming buildings, including the Castillo de San Marcos, a Spanish stone fort, and the Oldest Wooden Schoolhouse. After exploring the city streets, you can delve into the city’s history of piracy at St. Augustine Pirate and Treasure Museum or see where Spanish explorer Ponce de Leon likely made first landfall in the United States way back in 1513.

Traverse City, MI

Making it a charming trinity on this list for Michigan is Traverse City, the cherry capital of the United States. The National Cherry Festival is held here each July, although early May is the best time to visit for the cherry blossoms. Traverse City sits on a bay of Lake Michigan and the climate is as good for grapes as it is cherries. Many of the area’s 50 wineries offer free tastings. Nearby, Sleeping Bear Dunes contains impressive sandy bluffs plunging 450 feet (137m) down towards the lake. Traverse City is also a regional beacon for culture, with its Victorian-era City Opera House, many theatres, Dennos Museum Center art gallery, and the annual Traverse City Film Festival.