Many of America's main streets are lined with unique shops, family-owned bakeries and trendy boutiques. But these charming thoroughfares and boulevards are more than just locations for shopping and eating; they’re crucial to the towns and cities’ identities and create memories for both residents and visitors. From bustling sidewalks framed by historic old brick buildings to tranquil avenues canopied by ancient trees, this list pays tribute to their enduring appeal.
Read on to discover our ranking of America's most charming main streets...
A picturesque blend of centuries-old architecture and modern vibrancy, King Street serves as the cultural and commercial heart of Alexandria’s Old Town. This walkable historic thoroughfare, set against the backdrop of the Potomac River and cobblestone streets, boasts 200+ independently owned boutique shops and gourmet restaurants. The Torpedo Factory Art Center, a former naval munitions factory, is nearby on the corner of North Union and Cameron Street.
Annapolis may be Maryland’s state capital, but 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 popular throughout Europe during the 17th century. Located between Church Circle and City Dock, its five-block Main Street can't be missed with its busy sidewalks, views of the Annapolis Harbor and bustling businesses, including one of its original hotels the Maryland Inn, built in the late 18th century.
With nearby attractions including the Blue Ridge Parkway and Mountains, as well as the vibrancy of western North Carolina, Asheville’s Broadway Street and Biltmore Avenue are cultural hubs with an array of shops, dining experiences and the Asheville Art Museum. While the world-famous Biltmore Estate's chateauesque-style mansion requires tickets to enter, exploring the Biltmore Village is completely free and simply walking the historic area and taking in the English village-themed buildings is a must-do.
The town of Breckenridge, Colorado, was founded by General George E Spencer's prospecting company in 1859, and the Victorian architecture is still there for all to see. Main Street, which runs the length of the city, is known for its incredible shopping and dining scene, but it also serves as the central hub of everything Breckenridge with fun events, festivals, music, and an abundance of outdoor activities like stand-up paddleboarding and fly fishing. Once you park the car or take the shuttle in, you can walk almost anywhere, enjoying the Rocky Mountains and stunning views.
The entire city of Charleston is like a living museum. Originally called Charles Town in the 17th century, after King Charles II, the southern city was like a miniature London transplanted to the New World. Charleston’s historic downtown is the shopping and dining hub for the region. With its remarkable history and eclectic mix of fashion, art, antiques, home decor, and extraordinary food, King Street runs from Charleston Harbor to uptown and is one of the most vibrant and distinctive downtown districts in America.
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A byproduct of 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. Much of Main Street’s history is the stuff of American folklore. This is where the legendary gunslinger Wild Bill Hickok was shot dead, playing poker in a Main Street saloon in 1876. 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. Annual events such as Deadweird, Days of ’76 and Kool Deadwood Nights take place in the town.
Nestled within the Ozark Mountains, the Victorian town of Eureka Springs (which is on the National Register of Historic Places) is known for its winding streets that follow the hilly terrain. The snaking Main Street is bordered by Victorian-era architecture and has an array of art galleries, boutiques and restaurants. And its unique hillside setting, natural springs and historic ambiance give it a picturesque charm. Nearby, you can people watch in Basin Spring Park and see what life was like in the 1900s with a visit to the Historical Eureka Springs Museum.
The Downtown Franklin Association and its members are dedicated to preserving the history and charm of its central area. Twenty miles (32km) south of Nashville, the city's Main Street is the epitome of a storybook-perfect Southern town. You’ll find landmarks like the historic Franklin Theatre, dating back to 1937 and still hosting movies, concerts and shows today. While many of the buildings are historic in this 16-block district, it wasn’t until the mid-1980s that residents launched Main Street’s revitalisation, introducing specialty boutiques and restaurants.
This town gets its name from the mineral galena, an ore of lead, which has been mined in the area for centuries. It was once the largest steamboat hub north of St Louis, and was the home of President Ulysses S Grant. Galena's Main Street has a fun nickname: Helluva Half Mile. Here you’ll find more than 125 shops and restaurants, from candy and ice cream shops to spas, wine tasting and top dining options. And what makes the experience even more special is that it all happens along an authentic 1800s street with original buildings.
Whether you're looking for cosy coffee shop to start your day, or a fun family activity, downtown Lake Placid's Main Street, set against a backdrop of the Adirondack Mountains, has a unique mix of businesses and attractions, including the Lake Placid Olympic Museum, so every base is covered. Surrounded by the natural beauty of Mirror Lake, Whiteface Mountain, and enriched by the annual Lake Placid Film Festival, it embodies the iconic charm of Upstate New York.
This colourful street in the heart of Fort Lauderdale is full of fashion boutiques, art galleries, memorable restaurants, sidewalk cafes and bars. Las Olas Boulevard stretches from the beach at State Road A1A, immaculately lined with palm trees and beautiful people, and rises over the fabulous Intracoastal Waterway with magnificent views of the beach, million-dollar homes and spectacular yachts. The upscale boulevard is perfect for a stroll and ducking in and out of the cool breezeways.
If you’re looking for a taste of the Old West in the form of murals, old signs and historic brick buildings, head to Livingston, Montana. The transcontinental Northern Pacific Railway put L-Town on the map when it opened a station there – and the community became the first gateway town to Yellowstone National Park. Its Main Street used to be a muddy track bordered by wooden sidewalks, false-fronted stores and saloons. It might only be a few blocks long, but it’s packed with charm.
Blending historic attractions with original restaurants, shops and nightlife, South Main Street creates an authentically Memphis way to spend a few hours, an entire day – or a memorable night out. This district sits one block below the city’s historic Beale Street, and is also famous for its artistic characters, art-centric organisations and for being the setting of some of the Civil Rights Movement's most significant events.
During the summer months, Nantucket’s cobblestone Main Street, originally known as State Street, is bustling with pedestrians. Greek Revival, Colonial and Federalist storefronts are reminders of the world-renowned whaling industry that was here during the 1840s. These days, there are bookstores, galleries and antique shops, while fashion outlets like Salt Boutique and Blue Beetle keep everyone outfitted in nautical attire.
Founded by the French in 1714, Natchitoches is the oldest permanent settlement in the Louisiana Purchase. Front Street, a part of Jefferson Highway, along the Cane River Lake, is the town’s main thoroughfare, and is lined with historic buildings, shops and restaurants. A recent restoration project rehabilitated six blocks of historic streets, as approximately 300,000 roadway bricks were removed, cleaned and replaced. Many Native American and 18th and 19th-century European artefacts were discovered.
It’s not hard to see why Northampton has been named best small city in America. Tucked in a river valley 100 miles (161km) west of Boston, the ‘Paradise City’ has a rich history, an artsy college-town vibe, cool shops and boutiques, and an incredible array of excellent restaurants. Northampton’s Main Street (on the National Register of Historic Places) is its central hub. It regularly hosts exciting events and activities and features historical relics like the Academy of Music Theatre, the nation’s oldest city-owned theatre, built in 1890.
Local shops that line the streets of small-town America have always been part of their charm. None more so than on Washington Avenue in Ocean Springs on Gulf Coast Mississippi, which is included in this list because of its quaint galleries and boutiques, the Walter Anderson Museum of Art and the Peter Anderson Arts and Crafts Festival. At Coastal Magpie, you will find an exciting mix of antique furniture, fine art and handmade original gifts.
If you’re a fan of comedy drama Big Little Lies, you may recognise the beauty of Pacific Grove which is home to some of the filming locations from the hit TV show. Nicknamed ‘America's Last Hometown’, the city which hugs the Pacific Ocean 75 miles (121km) south of San Jose in Monterey County, has a historic downtown and romantic spot affectionately named Lovers Point. Its main street, Lighthouse Avenue, takes its name from Point Pinos Lighthouse, and is home to working art studios with gallery spaces and antique shops.
Settled by Dutch immigrants in 1847, this veritable ‘Little Holland’ is home to the largest working grain windmill in the United States and has a replica of a Dutch square named Molengracht, as well as a canal. That sits right off Main Street, which, thanks to its many grocery stores, market, cafes and bakeries, is a dream for foodies. The best time to visit Pella is the first week in May for the city’s annual Tulip Time Festival, when you can see more than 300,000 vibrantly blooming flowers.
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Located on a peninsula north of Seattle, the Victorian seaport of Port Townsend is known for its many 19th century-style buildings. Its waterfront area, home to the main road, Water Street, was designated a National Historic District in 1976. The city completed the £2 million ($2.7m) Water Street Enhancement Project in 2018, with new transit, pedestrian and bicycle facilities installed to enhance the streetscape. As well as the bustling Port Townsend Plaza, there are a few stores in the ‘underground’ off Water Street.
Originally a stop for stagecoaches heading west, Red Lodge boomed in the late 19th century when coal was discovered nearby. While many of the town’s storefronts and other buildings reflect European influences, Broadway Avenue is full of classic Old West saloons, cafes, and bed and breakfasts. It is the gateway to the Beartooth Highway – the northern access route to Yellowstone National Park and dubbed the ‘most beautiful road in America’.
While not that historic, downtown Rosemary Beach’s Main Street (created with the town’s Master Plan in 1995) is a stunning example of New Urbanism. A block from the Gulf of Mexico side is the chic 55-room Pearl Hotel, with its sun-drenched turrets and terraces and timeless black-and-white striped awnings. The Caribbean meets Charleston-style colourful storefronts on Main Street span several blocks to the north, while the locally owned shops and boutiques sell everything from books to baubles.
Nestled in the Santa Ynez Valley, Solvang looks and smells like Christmas all year round. It was founded in 1911 by Danes, which explains the windmill above Solvang Brewing Company, the statue of Hans Christian Andersen, and the Danish-style architecture and flora. Mission Drive is the main street in town. Wander the avenues, walkways and catacomb-like shopping nooks, where you’ll find all sorts of interesting Danish-themed souvenirs, and stop off at the local bakeries and confectioners for tasty traditional treats like aebleskiver (pancake balls).
Named after the British earl, Southampton was New York State’s first permanent English settlement. Today, this small but bustling and luxurious spot in the Hamptons is where New Yorkers spend their summers. Flanked by rows of trees, upscale fashionable boutiques, and Michelin-starred eateries, its Main Street epitomises the 400-year-old village, and the North Main Street Historic District was listed on the National Register of Historic Places in 1986.
Settlers arrived in Stillwater, 30 miles (48km) west of the Twin Cities and on the Wisconsin border, during the mid-1800s, enticed by lumber traffic along the St Croix River. This cute town of just under 20,000 residents boasts a five-block Main Street that is full of clothing boutiques, toy stores, art galleries and German and Swedish import shops, as well as delightful cafes, spas/salons, nightlife and great places to stay.
Known as the ‘Cherry Capital of the World’, the area around Traverse City is also famous for its freshwater beaches, vineyards and wineries and proximity to Sleeping Bear Dunes National Lakeshore. On Front Street, the town’s main drag, you’ll find indie bookstores and culinary shops filled to the brim with cherry-fused eats, as the trees overhead show off their natural displays. Plus, there’s the Friday Night Live street party every week during summer, and the Victorian-era City Opera House.
The city of Waitsburg, in the Touchet Valley near the eastern border of Walla Walla County, began to form in 1865 around a gristmill built by Sylvester M WaitIn. As it is in the heart of wine country, Waitsburg’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.
Although it was founded as a mining town in the late 19th century, Telluride became a major ski destination in the 1970s. West Colorado Avenue serves as the main drag, and is perfect for apres-ski, shopping and dining in the winter, or for a long summer stroll. The Mahr Building, standing in the place of the old San Miguel Valley Bank, is where Robert LeRoy Parker, aka Butch Cassidy, took part in his first robbery in 1889.
Georgetown’s M Street is considered one of the best shopping streets in the whole of the United States. Walking south on this iconic stretch of boutiques, restaurants and bars, along Wisconsin Avenue, leads to the Georgetown Waterfront Park along the Potomac River. Walking north brings you to Book Hill and a collection of independent shops, galleries and antique stores. One of the street’s most beloved landmarks is the circa-1766 Old Stone House, the city’s oldest still-standing structure.
Topping our ranking of America's most charming main streets is Broad City. 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, its historic main route. The six-room Broad Street Inn, originally built in 1870, is just a short walk from dining, shopping, wine-tasting and theatre experiences.