The 39 Most Beautiful Main Streets Across America
Between the major cities on the coasts of the United States are hundreds of small towns where a good portion of the American population lives today. Established over the last two centuries as the country expanded west, the majority of these municipalities have one thing in common: a charming main street. Lined with shops, restaurants, and other small businesses, these broad boulevards— often with their vintage flair intact—are a quintessential hub of any small community. Sure, European towns might have main streets with fairytale-esque cobblestones and half-timbered façades, but nothing says Americana like a paved road flanked by old brick buildings and hand-lettered signs. Here, a look at 39 of the most beautiful main streets across the country.
Photo: Denis Tangney Jr./Getty Images1/39Northampton, Massachusetts
Near the Five Colleges (including Smith College and the University of Massachusetts Amherst), Northampton’s Main Street—on the National Register of Historic Places—channels the free-thinking vibe with shops like Shop Therapy (ground central for tie-dye apparel) as well as Amherst Books. Main Street features historical relics like the Academy of Music Theatre (Renaissance Revival, built in 1891 as the first municipally owned theater in the country).
Photo: Leon Werdinger/Alamy Stock Photo2/39Walla Walla, Washington
In the heart of wine country, Walla Walla’s Main Street is home to a few tasting rooms, including Cayuse Vineyards (look for the canary-yellow storefront), and reminders of decades past, such as a towering antique clock outside of Falkenbergs Jewelers that dates back to the early 1900s. Many storefronts are tucked into Beaux Arts and Victorian buildings.
Photo: Mitch Diamond/Getty Images3/39Solvang, California
Does this Santa Barbara County town’s Mission Drive look Danish or what? There’s a reason: Solvang was founded in 1911 by Danes, which explains the windmill above Solvang Brewing Company and statue of Hans Christian Andersen, along with Danish-style architecture and flora. You can even pick up a Danish kringle at Mortenson’s Bakery, try aebleskiver (pancake balls), or sip the current chapter: winery tasting rooms, many made famous from the Sideways (2004) film.
Photo: Peter Ptschelinzew/Getty Images4/39Galena, Illinois
It probably doesn’t come as too much of a surprise that this town is named for the mineral galena, an ore of lead, which has been mined in the area for centuries. It has two other major claims to fame: It was once the largest steamboat hub north of St. Louis, and it was the home of President Ulysses S. Grant (and eight other Civil War generals). Its Main Street has a fun nickname: Helluva Half Mile.
Photo: Rick Lewis/Alamy Stock Photo5/39Rosemary Beach, Florida
While not nearly historic, downtown Rosemary Beach’s Main Street (created with the town’s Master Plan in 1995) is a stunning example of New Urbanism, with the sibling New Urbanism town of Seaside just a few miles west along 30-A. A block from the Gulf of Mexico side is the chic black-and-white Pearl Hotel. The West Indies–meets–Charleston–style colorful storefronts span several blocks to the north, retailing everything from books to baubles.
Photo: Getty Images6/39Pella, Iowa
Settled by Dutch immigrants in 1847, the town of Pella is a veritable “Little Holland.” It’s home to the largest working grain windmill in the country and has a replica of a Dutch square named Molengracht, complete with a canal, which sits right off Main Street. Visit in May for the annual Tulip Time Festival.
Photo: Stephen Saks/Getty Images7/39Port Townsend, Washington
Located on a peninsula north of Seattle, Port Townsend is known for its many Victorian-style buildings. Its waterfront area, home to the main road, Water Street, was designated a National Historic District in 1976.
Photo: Wesley Hitt/Getty Images8/39Eureka Springs, Arkansas
Set in the Ozark Mountains, this Victorian town is known for its winding streets that cater to the hilly terrain. (In fact, there are no traffic lights here as no two streets cross perpendicularly.) It’s not just Main Street that’s recognized as historic—the entire town of Eureka Springs is on the National Register of Historic Places.
Photo: Getty Images9/39Telluride, Colorado
Like many towns in the mountains out West, Telluride was founded as a mining town in the late 19th century, but it became a major ski destination in the 1970s. Colorado Avenue serves as the main drag, perfect for après-ski shopping and dining or a long summer stroll while browsing the windows.
Photo: csfotoimages/Getty Images10/39Franklin, Tennessee
Twenty miles south of Nashville, this burb’s Main Street conveys the storybook-perfect town. You’ll find landmarks like the historic Franklin Theatre, dating back to 1837 and still hosting movies, concerts, and shows today. While many of the buildings are historic, it wasn’t until the mid-1980s that residents launched the street’s revitalization, bringing in specialty boutiques, restaurants, and more.
Photo: Barry Winiker/Getty Images11/39Beacon, New York
Not every town on this list was built during the westward expansion. Two fur traders purchased the land from the native Wappinger tribe in 1683, and a few decades later, two villages were erected on the site. Today it’s best known as the home of contemporary art museum Dia:Beacon, which is a little ways off of Main Street, where you’ll find a collection of restaurants and quirky boutiques.
Photo: frankix/Getty Images12/39Pacific Grove, California
Salty air and ocean vistas further beautify Pacific Grove, which hugs the Pacific Ocean 75 miles south of San Jose in Monterey County. (All those Victorian homes and storefronts might look familiar if you tune into the next season of Big Little Lies.) On Lighthouse Avenue are plenty of working art studios with gallery spaces, plus antique shops like Fat Willy’s.
Photo: Anne Rippy/Getty Images13/39San Marcos, Texas
Turn-of-last-century buildings line San Marcos’s downtown streets, including Hopkins Street, where there’s everything from a rooftop bar to the Charles C. Cock House Museum (in the city’s oldest remaining residential building, a Greek Revival structure). The downtown’s square is a vibrant scene no matter what time of year.
Photo: J.T. Crawford/Paducah Life Magazine14/39Paducah, Kentucky
William Clark—half of the famous explorer duo Lewis and Clark—founded this town in 1827. General Ulysses S. Grant once occupied the city during the Civil War, establishing Paducah as a main supply center for the Union army. In 2013 the town was named a UNESCO Creative City of Crafts & Folk Art. While the main street is Broadway, you can find shops, galleries, breweries, and more across the entire historic district, which is managed by the town’s Main Street program.
Photo: Ken Wiedemann/Getty Images15/39Nantucket, Massachusetts
During the summer months, Nantucket’s Main Street is hopping with pedestrian traffic along the cobblestone streets. Greek Revival, Colonial, and Federalist storefronts are serious eye candy and reminders of the world-renowned whaling industry that was here during the 1840s. Shops like Blue Beetle keep everyone outfitted in nautical attire and ensure the home interior is just as fashionable (like at Nantucket Looms).
Photo: Witold Skrypczak/Getty Images16/39Brigham City, Utah
The first settlers in Brigham City, Utah, were a group of Mormons who arrived in the early 1850s. While the town suffered from economic hardship during its early decades, it boomed during World War II when the government built a major hospital there. Main Street nearly bisects the city perfectly.
Photo: Getty Images17/39Deadwood, South Dakota
Another byproduct of a gold rush—this time the Black Hills Gold Rush—Deadwood grew quickly in the 1870s. It was a true Wild West town, filled with casinos, saloons, and plenty of debauchery. Today it’s still a gambling town, with many historic gaming and drinking establishments lining Main Street, but it’s a much more orderly scene.
Photo: Stephen Saks/Getty Images18/39Livingston, Montana
The transcontinental Northern Pacific Railway put Livingston on the map when it opened a station in town. (It was the final place an engine could be serviced before traversing the Bozeman Pass.) The community then became the first gateway town to Yellowstone National Park. Main Street might only be a few blocks long, but it’s packed with charm.
Photo: Kent Kanouse via Flickr19/39Natchitoches, Louisiana
Natchitoches was actually founded by the French in 1714, making it the oldest permanent settlement in the Louisiana Purchase. Front Street along the Cane River Lake is the town’s main thoroughfare, and it’s lined with plenty of historic buildings housing shops and restaurants.
Photo: Getty Images20/39Bedford, Ohio
This suburb of Cleveland was founded in 1823 as settlers began building mills along the waterfall-lined Tinkers Creek. Broadway Avenue is the hub of Bedford’s historic district, which is listed on the National Register of Historic Places.
Photo: Getty Images21/39Red Lodge, Montana
Originally a stop for stagecoaches heading west, Red Lodge boomed in the late 19th century when coal was discovered nearby. The town saw an influx of European settlers, not to mention a large group of Native Americans seeking work in the mines, making its small population one of the most diverse in Montana at the time. Broadway Avenue is full of classic Old West saloons, cafés, and bed and breakfasts.
Photo: Joe Rebello/Getty Images22/39Staunton, Virginia
The birthplace of Woodrow Wilson was officially founded in 1747, though the area was settled about 15 years earlier. One of its most famous attractions? American Shakespeare Center's Blackfriars Playhouse, a re-creation of the playwright’s famous Blackfriars Theatre in London. Staunton’s Main Street was the first in Virginia to be awarded the National Trust for Historic Preservation’s Great American Main Street Award.
Photo: garyrennis/Getty Images23/39Traverse City, Michigan
This Northern Michigan town along Grand Traverse Bay, which flows into Lake Michigan, is Michigan’s cherry belt and the state’s most vibrant wine region (Madonna’s family has a winery in nearby Suttons Bay). On the main drag (Front Street), tucked under awnings, you’ll find two indie bookstores and culinary shops filled to the brim with cherry-fused eats, plus the Friday Night Live street party every Friday during summer. The crown jewel: the Victorian-era City Opera House, the oldest of three still standing in Michigan.
Photo: Mitch Diamond/Getty Images24/39Ashland, Oregon
When Reese Witherspoon emerges from the Pacific Crest Trail in Wild—the adaptation of Cheryl Strayed’s memoir of the same name—she’s in boho-chic Ashland, strolling along Main Street. This Rogue River Valley town is at the foot of Mt. Ashland, with 48 spots on the National Register of Historic Places, including its Downtown District, where the restored Ashland Springs Hotel, with its Romanesque arches and Tiffany-style stained glass, resides.
Photo: Jeremy Mason McGraw/Getty Images25/39Bentonville, Arkansas
While the country’s largest “general store” (Walmart) is headquartered here, Bentonville’s downtown core is cute and quaint. Main Street is also home to The Walmart Museum, snug on Main Street; and Sam Walton’s first five and dime. In more recent years, 21C Museum Hotel debuted on nearby NE A Street, introducing a cutting-edge angle.
Photo: Lawrence Sawyer/Getty Images26/39Stillwater, Minnesota
Along the St. Croix River, 30 miles west of the Twin Cities and on the Wisconsin border, this cute town of just under 20,000 residents boasts a Main Street that is the real deal with antique shops, eateries, and bed and breakfasts. Settlers arrived during the mid-1800s, enticed by lumber traffic along the river.
Photo: Josh Miller Photography/Getty Images27/39Nevada City, California
During the California Gold Rush, dozens of towns cropped up across the state, one of them being Nevada City. At its peak more than 10,000 residents crammed into the community, though today that population has dwindled to a more comfortable 2,800. Nevada City has largely retained the look of its earliest days, preserving many old structures along and around Broad Street, the historic main route that today is filled with dining options.
Photo: Don Smetzer/Alamy Stock Photo28/39Cedarburg, Wisconsin
Anchored by the Cedar Creek Settlement (home to a local winery) on Washington Avenue, this riverfront town 40 minutes north of Milwaukee features many stone buildings—including the Washington House Inn—built from limestone and fieldstone between the 1840s and early 1900s. Decent antiques shopping, along with a vintage movie theater and an arts center, make this a popular day-trip destination for residents of Milwaukee and Chicago.
Photo: jsolie/Getty Images29/39Virginia City, Nevada
Resembling the towns of the Old West movies, Virginia City features clusters of Victorian buildings established during the mining boom of the mid-1800s. But it’s anything but a ghost town. Gold Hill Hotel is one of Main Street’s oldest buildings (1861) and has welcomed guests again since its renovation during the late 1980s.
- Photo: Glowimages/Getty Images30/39
Washington, D.C.
Though it may not stand for “Main,” Washington, D.C.’s M Street, in Georgetown, is the center of the neighborhood, which was originally built along the C&O Canal as a tobacco port town. It featured a lumberyard, cement works, and even the Washington Flour Mill. More than two centuries later, in 1967, Georgetown was designated a National Historic Landmark. It’s also included in the National Register of Historic Places. One of the street’s most beloved landmarks is the circa-1765 Old Stone House, the city’s oldest still-standing structure.
- Photo: Michael Warren/Getty Images31/39
Cairo, Georgia
Situated on the Georgia-Florida state line, Cairo, on the Georgia side of the border, is a quaint small town made especially scenic courtesy of the Red Hills region’s farmland and timber. “The Hospitality City,” as it’s known within the state, boasts a main road that is its pièce de résistance.
- Photo: Peter Unger/Getty Images32/39
Bar Harbor, Maine
About three hours northeast of Portland, Bar Harbor, originally dubbed the Town of Eden in 1796, has always been a quietly luxurious summer retreat for the wealthy and powerful. In fact, throughout much of the late 19th century, such notables as Joseph Pulitzer, William Proctor, Mary Cadwalader Jones, Frederick Vanderbilt, George Vanderbilt, and Evelyn Walsh McLean built cottages on the island. At the time, it even rivaled Newport, Rhode Island.
The main street—appropriately called Main Street—is chock-full of charming local boutiques, which during the summer months are typically filled with visitors.
- Photo: Hisham Ibrahim/Getty Images33/39
Annapolis, Maryland
Annapolis may be the state’s capital, but it’s not exactly a sprawling urban oasis. It’s a classically quaint small town with 18th- and 19th-century homes and businesses lining brick roads. The city’s layout was mapped out in 1696 by Maryland’s governor, Francis Nicholson, who based his design on Baroque urban planning principles that had spread throughout Europe during the 17th century. He turned to Annapolis’s naturally existing topography when deciding where to put the city’s two most important structures: the statehouse and the Episcopal church. The former resides on the highest point in Annapolis and the latter on the second-highest.
Aside from being quite visible from their vantage points, the buildings also stand out among the others because they are located at the center of two circular roundabouts, with quite a few streets branching out from them. One of those streets is Main Street, a five-block-long brick-paved road that still has one of its original businesses, The Maryland Inn, built in 1776.
- Photo: Getty Images34/39
Breckenridge, Colorado
The town of Breckenridge, Colorado, was founded by General George E. Spencer in 1859, when Victorian architecture was in fashion. Main Street, which runs the length of the city, is flanked by buildings in this style, most of them dating back to the town’s inception. Today, of course, the centuries-old structures house more-contemporary businesses and restaurants, but the town itself and Main Street are still quite historic and provide a beautiful backdrop for anyone in pursuit of a wintery getaway.
- Photo: Lisa-Blue/Getty Images35/39
Charleston, South Carolina
The entire city of Charleston is considered a living museum because, since its inception in the 17th century, much has happened there. Originally called Charles Town, after King Charles II, the southern city was like a miniature London transplanted to the New World. Not incidentally, Charles Town was famously tolerant when it came to religion because the city’s leaders believed that a sense of acceptance would bring more residents and therefore more wealth.
The Revolutionary War brought an end to Charles Town’s economic boom—especially because so much of the city had been torched. When the war finally came to a close, the city was renamed Charleston. The Civil War further broke the city down, leaving locals too destitute to rebuild. Instead, they just fixed what was already there. Main Street, for instance, is dotted with centuries-old pastel-painted structures.
- Photo: Barry Winiker/Getty Images36/39
Southampton, New York
Flanked by rows of trees, fashionable boutiques, and Michelin-starred eateries, Southampton’s Main Street is a charming representation of the 400-year-old village itself. In fact, Southampton was New York State’s first permanent English settlement and was named after the British earl of Southampton. Today, of course, it’s a bustling, luxurious—albeit small—spot where New Yorkers spend their summers.
- Photo: Jonathan D. Goforth/Getty Images37/39
Somerset, Kentucky
Somerset, Kentucky, is a small town of just over 11,000, but its North and South Main Streets, which meet in the middle at Fountain Square, are always dotted with people. The fountain, which dates back to the early 19th century, is the city’s centerpiece, where locals go for live music, political rallies, and anything in between.
Photo: Joshua J. Cotten/Unsplash38/39Memphis, Tennessee
South Main Street sits just one block below the city’s historic Beale Street, a three-blocks-long road dotted with nightclubs, restaurants, and shops and known for being a melting pot of live music. South Main, however, is also famous for its artistic characters, including those who own the local businesses and art-centric organizations. And it’s home to some of the most memorable events of the Civil Rights Movement.
- Photo: PapaBear/Getty Images39/39
Chagrin Falls, Ohio
Chagrin Falls is a suburban village just outside Cleveland and is named for the nearby waterfall on the Chargin River. It's a small town of 4,000 with a Main Street that lives up to its name. This is where the most popular cafés and businesses are. Plus, they’re all housed in enchanting centuries-old structures that are protected by the local government.
