America’s 25 Cutest Main Streets in Small(er) Towns

Live oaks? Check. Red bricks? Check. Cast-iron balconies? Check. Front Street exudes southern charm with all the antebellum trimmings in this sultry Louisiana town, established four years before New Orleans, in 1714 (and, by the way, is pronounced nak-a-tish). Don’t miss Kaffie-Frederick General Mercantile, the state’s oldest continuously operating hardware store (since 1863), where you can still find classic toys like the Radio Flyer wagon. The award-winning Louisiana Sports Hall of Fame & Northwest History Museum on the street’s north end is a can’t-miss as well.

No, you’re not on a western movie set. Placerville is a veritable 19th-century gold town in the Sierra Nevada foothills filled with boomtown charm. Though these days, Placerville is experiencing another kind of boom.. Just check out the variety of unique shops that line its picturesque Main Street and you’ll see what we’re talking about: an olive oil shop, a yarn shop, a cheese shop, a bath shop, a chocolatier … this is not your standard miner fare. That said, the Placerville Hardware Store is the oldest hardware store west of the Mississippi (1852), and the Historic Cary House Hotel is right out of the history books.

Wine lovers, rejoice! Walla Walla’s tree-shaded Main Street boasts 39 tasting rooms showcasing regional wineries. But that’s only one reason to stroll along this revitalized pedestrian paradise, where cafés, boutiques, bookstores and antique shops occupying gorgeous Victorian and Beaux-Arts buildings offer plenty of diversions. Make a full day of it with a concert at the Walla Walla Symphony, the longest continuously operating American symphony orchestra west of the Mississippi (since 1907).

Main Streets don’t get much more quintessential than Stowe’s, where clapboard buildings filled with shops, restaurants, and galleries (including Shaw’s General Store, established in 1885) compete for cuteness. Add the white-steepled church and covered walking bridge, all in the shadow of Mount Mansfield, and voilà—instant Christmas card scene. For a nostalgic overdose (in a good way), stay at the Green Mountain Inn, built in 1833 as a private residence.

Every day in Rockland should begin over coffee at Rock City Coffee, with its primo harbor view. And only then should you begin your explorations of this absolutely charming main street. The redbrick Italianate-style buildings are historic, built in the 19th and 20th centuries at the peak of the town’s shipbuilding and lime processing businesses. And what fun it is to check them out. Some highlights: Main Street Markets’ healthy provisions to pack the best picnic lunch ever; the Farnsworth Art Museum’s glorious collection of American art; and galleries galore.

You feel mighty welcomed to this main street, given the grand sign arching over the entrance to Washington Avenue: Howdy Folks! Welcome to Golden … Where the West Lives. The historic buildings lining the street give testament to Golden’s gold-mining heritage. Though these days it’s all about the unique boutiques, restaurants, craft breweries, galleries, and recreational outfitters (the nearby Clear Creek beckons kayakers, anglers, and tubers). Keep an eye out for the building where the first Colorado legislators met when Golden was the territorial capital.

The country’s first major gold rush didn’t take place in California but in Dahlonega (in 1828), a fact celebrated at the Gold Rush Days festival in October. Main Street here, though, centered on its historic public square, is more Appalachian than western in flavor, with plenty of places to shop for unique gifts, gallery hop, or catch a show at the beautifully restored Holly Theater. As the 2016 winner of the Great American Main Street Award, you know this one’s got to be good.

Boasting one of the state’s best collections of Victorian and pre-World War I architecture, Georgetown Square is, quite simply, beautiful. The Williamson County Courthouse stands in the center of it all, with the Williamson Museum across the street offering a history primer (and, so they say, providing a home to at least 6 ghosts that may or may not have been involved in old-time shootouts). Don’t miss Sincerely Yours 1848, a little hipster boutique named for the date Georgetown was founded; and 600 Degrees Pizzeria and Draft House, living up to the sign over the door: Friends Meet Here. And yes, in case you think you’re having déjà vu, it’s possible you’ve already seen Georgetown Square, in What’s Eating Gilbert Grape, Dazed and Confused, Varsity Blues, Friday Night Lights, and other productions.

For decades, this part of town was a no-go in a city famed for hosting the Master’s Golf Tournament since 1934. But a revitalization program that started with the artists in the ‘90s is bringing new life to the historic facades lining Augusta’s main street. Little by little, indie shops, loft apartments, and exciting restaurants are joining the galleries, enticing visitors with the likes of Soul Bar, Nacho Mama’s, Sky City (which has hosted hundreds of local bands and even some big-name ones), and Craft & Vine, a sophisticated place for cocktails and creative bites.

Don your little black dress and head out for the evening on Columbia’s buzzing Main Street. Say what? Yes, indeed, locals are quick to tell you that just five years ago it wasn’t like that. For years this neighborhood wallowed in despondency, until one by one, the businesses started coming, so now there’s something going on both night and day. You have old-timey Mast General Store and the Nickelodeon, aka The Nick, which is always putting on creative programs (including the annual Indie Grits film festival). Well-regarded restaurants include Bourbon and The Oak Table, perched near the state capitol. The Columbia Museum of Art sits right on Main, currently undergoing a $2 million renovation. But there’s even hipper stuff going on here, including Good Life Café (an organic, raw, vegan restaurant), The Grand (a boutique bowling alley), and Lula Drake Wine Parlour. And more keep coming.

Rapid City may be near Mount Rushmore, but it has something that the famous presidential cliff carving doesn’t have: life-size bronze statues of every president since George Washington (Obama just debuted). And many of them line Main Street, providing a truly patriotic flair (pick up a guide at the City of Presidents Info Center on the corner of 7th and Main). But there’s much more here than presidents. Main Street has well-preserved brick buildings filled with lively restaurants, boutiques, galleries, and bars. And the heart of it all is fun-filled Main Street Square. Here, fountains dance to music, a massive public art project called The Sculpture Project: Passage of Wind and Water stands tall, and more than 200 events take place each year; favorites include the Cruiser Car Show and Street Fair; Scare in the Square; and Holiday Celebration & Winter Market.

The spirit of the West lives on along Ketchum’s very strollable, tree-shaded Main Street, where historic cabin-esque buildings sit pretty in the shadow of the surrounding jagged peaks. Today they contain one-of-a-kind boutiques selling everything from outdoor gear (notably Sturtevants) to ski rentals for the slopes (Sun Valley is nearby!) to local art to trendy fashions. Among the restaurants, many with outdoor seating for sunny weather, seek out Pioneer Saloon, as famed for its Jim Spud and steaks as for its taxidermy décor.

Brick-and-wood buildings from the 1880s gold-rush era line this endearing little town’s main drag. Though today they’re filled with hipster cafés, indie boutiques, and wine-tasting rooms (we’re in serious wine country here in the Applegate Valley). It’s the sort of place to loll away a sunny afternoon, poking into shops and chatting over coffee, (though winter brings a dash of old-fashioned tradition with the Victorian Christmas holiday celebration). Favorite stops: La Bohéme and Cotton Broker for fashions, Pot Rack for the culinary connoisseur, and WillowCreek Jacksonville and Carefree Buffalo for locally made gifts.

Art and design is what it’s all about on this main street, the first tipoff being the whimsical, life-size public statues scattered about (a dog-walking businesswoman in a red suit, a springtime woman dancing with flowers). From there, explore interior design shops, art galleries, and showrooms. When it’s time for sustenance, pop into Woody’s restaurant, which occupies a former library, or Peace Water Winery, which donates half its proceeds to charity.

If you want to get your German on, MainStrasse in Covington evokes the city’s Teutonic roots. The place buzzes with one-of-a-kind shops and restaurants in Federal, Victorian, and Italianate buildings, all anchored around a German Gothic clock tower with mechanical figures that play out the Pied Piper of Hamlin story (aka glockenspiel). Some of the businesses remain German in flavor (Strasse Haus, Piper’s Café, Otto’s Restaurant), at least in name. A walking tour is available from MainStrasse Village Association.

It may have been rough and tumble in the olden days, but this Wild West town has changed its ways. Two restored buildings led the way for Main Street’s comeback: The century-old Freight Station, now the visitor center; and 1948 Broadway Theater, an intimate space that draws thousands of people for live performances. In between, mom-and-pop shops, indie boutiques, and gift shops offer superior shopping. Among favorite festivals, Rods & Rails Car Show brings hundreds of classic cars all along the street.

If you squint, you can see into the past. Albany Street appears straight out of the 19th century, when genteel tourists once headed to Cazenovia by train, drawn by its picturesque location on Cazenovia Lake. Things haven’t changed much, as visitors stroll down Albany Street, popping into antique shops, chi-chi boutiques, and sidewalk cafés occupying historic buildings. Must-dos: LillieBean for eclectic clothing; Cazenovia Artisans for local art; and the Pewter Spoon Café & Eatery. That’s all fine, but for something truly off-the-beaten-path, be sure to stop by the Museum at the Cazenovia Public Library, showcasing an ancient Egyptian mummy, early Native American tools, and more neat stuff.

The gracious, antique-filled General Lewis Inn sits along Washington Street on the edge of town, built around a brick residence dating from the early 1800s (when Lewisburg was just a small frontier outpost). But keep walking west on Washington and you’ll discover a town firmly planted in the 21st century, with cool art galleries and innovative eateries — many housed in Georgian and late-Victorian-style buildings. Popular stops Stardust Café for farm-to-table fare and Harmony Ridge Gallery for American crafts.

Look up when you’re strolling down this sweet Shenandoah Valley town’s main street; otherwise, you’ll miss the spectacular show of Victorian architecture rising above. Much can be attributed to the talented architect TJ Collins, who designed or remodeled nearly 200 buildings in the town in eclectic styles (including Beaux-Arts, Richardsonian Romanesque, even Egyptian revival). That said, you’ll be forgiven if you’re sidetracked by the wealth of enticing destinations within these buildings. Some to explore: Cranberry’s Grocery & Eatery, Clocktower Restaurant & Bar, the Beverley Cigar Store, and many used bookstores.

A mini Williamsburg without the frills. That’s what Delaware Street (and the rest of New Castle) feels like. Dutch colonial governor Peter Stuyvesant first laid out New Castle’s town grid in 1651 (about 13 years after Williamsburg), its main street leading up from the Delaware River since Day One. The town grew from there, but not too much. You can still imagine cattle grazing on the village green, the Colonial goings-on at the Amstel House (now a museum), and the excitement when the Declaration of Independence was first read to the citizens of Delaware in 1776 from the balcony of the compact courthouse.

Get your kicks on Albuquerque’s Central Avenue, the original route through town of the fabled Route 66. You’ll still find some of the original businesses, including Tewa Motor Lodge, with its neon sign; beloved Loyola’s Family Restaurant, serving up American-diner and New Mexican staples since the ’50s; 66 Diner, in a converted 1940s-era Phillips 66 gas station; Lindy’s, quite possibly the oldest Route 66 reststop in New Mexico; and Skip Maisel’s Indian Jewelry and Crafts, a real-life trading post that’s been in the same family since the ’30s. But it’s not all about nostalgia. The section through Nob Hill especially thrives with modern-day indie shops, swish dining, galleries, and chi-chi nightspots.

There was a town here long before it hosted a famous battle, as attested by the historic stone structures lining Steinwehr Avenue. Of course, every other building these days houses a battle-themed souvenir shop, but beneath it all is a real sense of old-time USA. Historic Dobbin House is in the center of it all, offering lodging and food since 1776 (go fancy in the dining room or more casual in the tavern). From here, you can head up toward the military park, passing by Gettysburg Battle Theatre, Gettysburg Diorama, and Lincoln Train Museum. But it’s in the other direction where you’ll find the real main street feel (kinda), with eateries, shops, and a brewery and brewpub (Appalachian Brewing Co.). You’ll hit Baltimore Street, which has more historic houses and museums. And don’t be surprised if you see a latter-day soldier reenactor in period garb just hanging out; this is, after all, Gettysburg.

Most of the mid-19th-century buildings belonging to the town’s Dutch settlers were devastated in the fire of 1871, but that didn’t stomp out the town’s Dutch spirit. They rebuilt, and today this historic thoroughfare’s Victorian buildings boast trendy boutiques, intimate restaurants, and the venerable Knickerbocker Theatre. It’s never more beautiful than springtime, with its overflowing flowerbeds (including, naturally, tulips). That said, winter’s ingenious sidewalk snow-melt system ensures year-round activity.

If you think you’ve seen this sweet main street before, it’s very possible you have. The darkly comedic Oscar-nominated drama Three Billboards Outside Ebbing, Missouri was primarily filmed here. The misty Blue Ridge Mountains frame the early 20th-century storefronts, and you’ll have a fun afternoon exploring its one-of-a-kind shops and restaurants, including Dixie Mae Vintage Market, Jackson’s General Store, and Black Rock Outdoor Company. Given its old-timey feel, the last thing you might expect is a latter-day brewery scene, but there you have it, two primo breweries including Balsam Falls Brewing and Innovation inviting you to taste their brews.