Many of America's main streets are lined with unique shops, family-owned bakeries, and trendy boutiques. But these charming thoroughfares are more than just places to shop and eat; they’re vital to their towns' identities. From bustling sidewalks framed by historic brick buildings to tranquil avenues shaded by ancient trees, these streets have timeless appeal – and we’ve ranked the 36 best to inspire your next trip.

Read on to discover our ranking of America's most charming main streets...

Congress Street is Portland’s main artery, linking the Old Port to the thriving arts district. Lined with Victorian architecture, indie bookstores, and acclaimed restaurants, it captures the spirit of Maine’s largest city. Highlights include the State Theater, the Wadsworth-Longfellow House, and the Portland Observatory (pictured), the country’s last surviving maritime signal tower.

Canyon Road is the heart of historic Santa Fe. This winding, adobe-lined street is packed with over one hundred art galleries, studios, boutiques, and restaurants along just half a mile. Once a footpath linking the Santa Fe Plaza to the mountains, it now showcases Pueblo heritage and a global arts scene, making a walk here an essential Santa Fe experience.

Once a silver mining boomtown, today Park City is best known for its world-class ski resorts and the Sundance Film Festival. Historic Main Street, which winds through a picturesque mountain valley, is lined with colorful 19th-century buildings housing art galleries, restaurants, and boutique shops – blending Old West charm with cosmopolitan flair. 

A blend of centuries-old architecture and modern vibrancy, King Street is the cultural and commercial heart of Alexandria’s Old Town. This walkable thoroughfare, set by the Potomac River, has over two hundred boutique shops and restaurants. Nearby, the Torpedo Factory Art Center, once a naval munitions factory, now houses artist studios and galleries.

With nearby attractions including the Blue Ridge Parkway and Mountains, 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 chateau-style mansion requires tickets to enter, exploring the Biltmore Village is completely free and simply walking the historic area to take 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 here 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.

Charleston feels like a living museum. Originally named Charles Town after King Charles II, the city was founded in 1670 and later moved to its current site in 1680.

Today, its historic downtown is a regional hub for shopping and dining. At its heart is King Street, stretching from the harbor toward uptown, and known for its blend of fashion, antiques, art, and standout Southern cuisine.

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Born of the Black Hills Gold Rush, Deadwood boomed in the 1870s as a true Wild West town, packed with saloons, casinos, and scandal. Main Street is steeped in folklore – it was here that gunslinger Wild Bill Hickok was shot dead while playing poker in 1876.

Today, Deadwood remains a gambling town, but a far tamer one, with historic gaming halls and bars still lining Main Street. The town also hosts lively annual events like Deadweird, Days of ’76, and Kool Deadwood Nights.

Nestled within the Ozark Mountains, the Victorian town of Eureka Springs 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.

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. Just 20 miles south of Nashville, the city's Main Street is the epitome of a storybook-perfect Southern town.

You’ll find the historic Franklin Theatre, dating back to 1937, 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 revitalization, 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 cozy coffee shop 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.

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 colorful street in the heart of Fort Lauderdale is full of fashion boutiques, art galleries, memorable restaurants, sidewalk cafés, and bars. Las Olas Boulevard runs from the beach at State Road A1A, lined with palm trees, and crosses the Intracoastal Waterway, offering views of the coast, luxury homes, and yachts. It’s ideal for a relaxed stroll and browsing the breezy, upscale shops.

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 here – 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-front 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 organizations, 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 artifacts were discovered.

It’s not hard to see why Northampton has been named best small city in America. Tucked in a river valley, 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 Theater, the nation’s oldest city-owned theater, built in 1890.

What the least populous state capital in the US lacks in size, it more than makes up for with the sheer scale of its niceness. Nowhere is this truer than on Montpelier's Main Street, with its rich tapestry of independent shops, restaurants, and historic buildings. 

The street, which suffered serious fire damage in 1875, has two charming churches in the form of Bethany Church, built in 1808, and the Unitarian Church of Montpelier, built in 1864. Pictured here, we see Montpelier City Hall, a four-story structure opened in 1909.

Local shops have long been part of small-town America’s charm – especially on Washington Avenue in Ocean Springs, known for its quaint galleries, boutiques, the Walter Anderson Museum of Art, and the Peter Anderson Arts and Crafts Festival. At Coastal Magpie, you’ll find a unique mix of antique furniture, fine art, and handmade gifts.

Grand by name, grand by nature. The main street running through the heart of Howell, Michigan, is home to several historic buildings that now house unique shops and eateries.

It's here where you'll find the Howell Opera House, built in 1881, and the ever-popular 2FOG's Pub, a subterranean speakeasy-themed haunt that offers craft beers, cocktails, and shuffleboard.

If you’re a fan of the comedy drama Big Little Lies, you may recognize the beauty of Pacific Grove, home to some of the filming locations from the show. Nicknamed ‘America's Last Hometown,’ the city, which hugs the Pacific Ocean 75 miles south of San Jose in Monterey County, has a historic downtown.

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, markets, cafés, 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 $2.7 million 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.

If sidewalks could talk, they'd have some stories to tell you about this once-infamous street in Utah. Between 1869 and the early 1950s, this stretch was rife with gambling, narcotics, robbery, and murder. 

These days, things couldn't be more different. Watched over by the Union Station sign at one end and epic mountain terrain at the other, Ogden's main street is now home to top restaurants, trendy pubs and bars, charming independent shops, and a thriving creative scene with must-visit art galleries.

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, cafés, 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.’

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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 timeless black-and-white striped awnings.

The Caribbean meets Charleston-style colorful 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. 

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 epitomizes 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 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 cafés, 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.

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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.

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). There's also reminders of decades past, such as a towering antique clock outside of Falkenbergs Jewelers that dates back to the early 1900s.

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 just over 3,000.

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 theater experiences.

Annapolis may be Maryland’s state capital, but it’s a classically quaint small town with 18th and 19th-century buildings 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.

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. Fast forward to today, this major thoroughfare in the Rockies has stolen our hearts and topped our 'best main street' rankings.

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