America’s Greatest Main Streets
Driving across America, it’s all too easy to lose your mooring amid the commercial thicket of the same old fast-food outlets and big-box stores.
But push on a mile or two beyond the interstate exit, and you may discover a town that’s anchored by a distinctive Main Street—one with grand architecture, eclectic small businesses, and community-oriented features like a park or theater. Often it thrives thanks to locals who have made a conscientious effort to fight the general decline of Main Street.
Related: America’s Best Little Beach Towns
The work of such activists and preservationists is acknowledged each year by the National Trust for Historic Preservation’s Great American Main Streets Awards and by the American Planning Association’s Great Places in America: Streets. We scoured their recent designations to select the most vibrant, distinctive downtowns worth the trip.
You’ll find these great Main Streets across the U.S., from mining towns like Silver City, NM, to stately, red-brick Staunton, VA. Yet our list does skew east of the Mississippi, favoring towns that were established before the age of the automobile—and so display the DNA of a pedestrian and bike-friendly environment.
Not that a walkable layout can guarantee a thriving Main Street. Take York, PA, where the 1978 shuttering of the last of four downtown department stores triggered a period of decay. The turnaround was slow going, as landowners aided by various programs renovated nearly every Victorian and Classical Revival façade. Now, on the first Friday of each month, local businesses stay open late, with special events and discounts.
Port Townsend, WA, went through its own reinvention. Expecting a shipping boom, 19th-century residents built out the town in high Victorian style—only to find themselves on the wrong side of Puget Sound when the railroads connected to Seattle. It’s been reborn as an arts center around the main drag, Water Street.
Second chances are just as American as a homespun Main Street, and with the recent economic downturn have come do-it-yourselfers seeing opportunity in cheap abandoned storefronts and converting them into bakeries or boutiques.
So it’s well worth driving the extra few miles to see what Main Street lies ahead. Let us point you in the right direction.
Galena’s Main Street bends gently as it follows the Galena River (a tributary of the Mississippi) and presents a medley of brick storefronts and bayfront windows, many in an Italianate style. This is the home turf for chocolate shops and galleries—and the second home of many Chicagoans who escape the Windy City three hours away. Trolley cars depart from Main Street for area wineries, and at the intersection with Water Street, you can turn onto a riverfront walkway.
Worth a Stop: DeSoto House Hotel has welcomed prominent guests since 1855. Locals flock here, too, for events such as a trivia quiz night in honor of Ulysses S. Grant’s birthday.
Port Townsend, WA
Expecting a shipping boom, 19th-century residents built out Port Townsend in high Victorian style starting in 1851. The town found itself on the wrong side of Puget Sound when the railroads connected to Seattle, 40 miles across the way. Yet much of the original exuberance remains; the historic town of 9,000 has been reborn as an arts center. Its most photographed landmark remains the blue-and-white Hastings Building with bay windows at 833-839 Water Street.
Worth a Stop: Rose Theatre, a 1907 former vaudeville theater lovingly restored and now showing contemporary movies. Worth the ticket price for gawking alone.
At the outskirts of the Dallas-Fort Worth Metroplex, Denton is its own full-blown city, with a population of 120,000 and two state universities. The walkable downtown core is built around a classic courthouse square, lending some flair and sense of community. (A stop by the museum housed in the 1896 courthouse explains how Denton evolved.) A thriving local music scene—proto-hipster band Brave Combo is based here—supports many live music venues not far from the square.
Worth a Stop: Rooster’s Roadhouse, where regulars favor the brisket burger and the pit barbecue plates (slogan: Red Neck, White Trash, Blue Collar).
In 1978, the last of four major department stores in downtown York was shuttered, triggering a period of decay. Over time, landowners aided by various programs have spruced up and restored nearly every façade—with great examples of the late Victorian and Classical Revival styles. Stroll Market Street for the most striking examples. On the first Friday of each month local businesses stay open late, with special events and discounts.
Worth a Stop: Food vendors have been hawking their goods at Central Market since 1754. Enjoy a quick meal at one of the market’s nearly two dozen restaurants and lunch counters.
This is Main Street in miniature. Wallace is home to fewer than 1,000 residents, but has a tidy, enchanting downtown flanked by steep pine-studded mountains. The main commercial drag of Bank Street is a classic Main Street, with elegant brick buildings done up in full Italianate style, suggestive of the silver boom that once gripped this remote part of northern Idaho.
Worth a Stop: One of those storefronts houses the Oasis Bordello Museum. On a short tour, trace the history of one of five Wallace bordellos that once, um, served the mining community.
Walk along Center Street, with its boutiques and bakeries, and you’ll soon understand why this bucolic river valley town of 3,200 now attracts well-off rusticators, drawn by the quiet life and grand historic homes. There’s little trace of Woodstock’s heritage as a prosperous 19th-century center of industry; even the power lines have been buried. Center Street divides at The Green, an oval park fronted by colonnaded houses and its own covered bridge.
Worth a Stop: Billings Farm and Museum is a lovingly maintained farm at the edge of town that showcases what was state of the art in agriculture circa 1871.
Ann Arbor, MI
University of Michigan students make up more than a third of the population of 113,000, which ensures a downtown full of activity. South Main Street—which has been a commercial hub since the city was laid out in 1824—was designed with pedestrian needs in mind, and offers enough brewpubs, art galleries, and delis to feed mind, body, and soul. Look up to admire the arched windows on upper floors above local retail shops.
Worth a Stop: The Ann Arbor Hands-On Museum is for kids who want to geek out; some 250 interactive science and technology exhibits both entertain and educate.
Saratoga Springs, NY
Historic Broadway Avenue looks like a Main Street on steroids, with grand buildings of Beaux-Arts and Colonial Revival styles. It feels almost heroic in scale, but when crowds fill the streets to browse and nosh, it takes on a more accessible feel. Sidewalk cafés and benches beside flowerbeds are perfect for people-watching—especially when the tony thoroughbred set comes to town for the summer horse-racing season.
Worth a Stop: Saratoga Spa State Park captures a slice of yesteryear, when visitors thronged here for the healing waters.
Eureka Springs, AR
The entire town of Eureka Springs in the Ozarks is on the National Register of Historic Places—no surprise as the streets are imbued with a cheerful Victorian charm. They twist and turn through the hilly terrain; catch the town trolley if you need a break. The first settlers were attracted by natural springs believed to be curative. Visitors today are more likely to come for the eclectic music and arts scene and to stay at one of the Queen Ann–style B&Bs.
Dry docks and cranes rising from the shipyard along the banks of the Kennebec River just south of downtown speak to the town’s nickname, the City of Ships. Bath itself is compact, brick-solid, and walkable. Explore leafy Front Street, with its brick buildings and an outpost of Reny’s, a small discount department store chain that’s a throwback to an earlier era. Detour down side lanes for bakeries, restaurants, and variety shops.
Worth a Stop: The Maine Maritime Museum gives a comprehensive, entertaining overview of Bath’s noble shipbuilding history, from wood to steel.
Paso Robles, CA
Midway between Los Angeles and San Francisco, this community of 30,000 was founded around natural hot springs. More recently, some 200 wineries have put down stakes in nearby hills, bringing new life to a once-moribund downtown. Visitors can take in wine tastings, exhibits, and movies around a square lined with buildings that range from adobe-style to high Victorian.
Worth a Stop: Learn more about the region’s Pinot Noirs and Zinfandels by signing up for a five-hour excursion with Paso Robles Wine Glass Tours.
The hometown of President Woodrow Wilson is twice lucky, blessed with the backdrop of the Shenandoah Valley and the main artery of Beverley Street, whose brick buildings amount to one of the highest concentrations of showy late-19th-century architecture in any U.S. town. It’s no wonder Staunton was the first in Virginia to win a Great American Main Street award from the National Trust for Historic Preservation, which singled out the Blackfriar’s Playhouse, a recreation of Shakespeare’s London theater.
Worth a Stop: The free Camera Heritage Museum tells the story of photography through a collection of nearly 2,000 historic cameras.
Silver City, NM
This mining-boom town’s original Main Street washed out in floods in 1895, leaving a 55-foot ditch. (The resulting ravine is now a leafy park.) Merchants started selling out their back doors on Bullard Street, turning the town around literally and figuratively. Silver City now serves as an arts anchor for the region, with more than a dozen galleries. The colorful buildings themselves have an artistic flair, some with false fronts, others with Rococo brick cornices.
Worth a Stop: Diane’s Restaurant, famous for the Hatch Benedict served at brunch—made with chile-cheddar toast and famous Hatch chiles.
This quiet town of 18,000 was first settled in 1714—four years before anyone thought to take up residence in New Orleans, four hours to the southeast. The downtown faces the Cane River and has a decidedly southern feel thanks to winsome buildings along Front Street festooned with balconies and cast iron, not to mention a waterway lined with live oaks. You may recognize it from the film Steel Magnolias.
Worth a Stop: A block off Front Street is Lasyone’s Meat Pie restaurant, serving a Civil War–era favorite: an empanada-type dish stuffed with mixed beef and pork.
It’s a long drive from anywhere to Littleton in northern New Hampshire—so good thing that this community of 6,000 along the Ammonoosuc River has a vibrant, self-sufficient Main Street. The streetscape is a pastiche in progress, with everything from the Neoclassicism of the 1850 Thayers Inn up to the austere Modernism of the last mid-century. Chutters sweetens the neighborhood and boasts the world’s longest candy counter at 112 feet.
Worth a Stop: Just L Modern Antiques offers a reasonably priced selection of Midcentury Modern antiques.
As you stroll the thriving riverfront district of Beloit, it’s hard to imagine that it was once a faded downtown, depressed by the loss of factory jobs and the lure of suburban malls. Twenty years ago, a forward-thinking group of boosters stepped in to restore many buildings as mixed-use spaces—galleries, bookshops, music venues—and to launch a weekly farmers’ market. Now everyone’s a booster: locals brag about their 3.5 miles of bike paths, more than 20 works of public art, and the college town’s new reputation as a performing arts magnet.
Worth a Stop: The Angel Museum for its remarkable collection of 11,000-plus angels, including 600 black angels donated by Oprah Winfrey. Or the more down-to-earth pleasures of a Beloit Snappers minor league baseball game (tickets from $5.50) promises a big taste of small-town charm.
Red Lodge, MT
Think Calamity Jane and Buffalo Bill Cody might look at home walking by Broadway Avenue’s Wild West façades? You’re right: both legends spent time in Red Lodge during its late-19th-century heyday. The Sundance Kid once robbed a bank on Broadway—lending it even more sepia-toned pedigree. The restored two-story shops, restaurants, and galleries are framed by the spectacular Beartooth Mountains; in fact, Broadway is part of an 80-mile-long Mainstreet to Mountains Rocky Fork Trail used to access the wilderness just outside town limits.
Worth a Stop: Join Buffalo Bill and Calamity Jane on the guest register at the Pollard Hotel, built in 1893 and still the place to stay.
Located above the Tombigbee River in northeastern Mississippi, Columbus is perhaps most famous for being the birthplace of Tennessee Williams. The Victorian house where the playwright grew up reopened as the town’s official welcome center in 1993 after being relocated to Main Street among small shops and restaurants that serve classic southern cooking. An increasing number of locals have chosen to move into apartments above such businesses, adding to the buzz of this downtown.
Worth a Stop: Located just off Main Street, the Hitching Lot Farmers’ Market runs from April to October with special Saturday events including live music plus watermelon-seed-spitting and corn-shucking contests during summer months.
Fort Pierce, FL
In 2004, two back-to-back hurricanes hit this town just about an hour north of West Palm Beach, ravaging the historic City Hall and the 1923 Sunrise Theatre. Despite the setback, the community rallied to rebuild this waterfront neighborhood of palm-tree-lined sidewalks—winning a 2011 Best Main Street designation from the National Trust for its efforts. For a dose of small-town charm, swing by restored P. P. Cobb General Store or the Fort Pierce Jazz Society’s Saturday Arts & Crafts Market.
Worth a Stop: Fully renovated to its former glory, the 1,200-seat Sunrise Theatre hosts live music and comedy acts that pair nicely with dinner downtown.
Although Nantucket—all 105 square miles of it—is a designated National Historic District, its cobblestoned Main Street is the island’s historic heart. Lined with grand Greek Revival buildings, elm trees, and countless benches, the street’s mix of chic boutiques and old-fashioned storefronts (selling needlepoint belts, saltwater taffy, and anchor-shaped door knockers) leads right down to the busy harbor, once the world’s whaling capital. The best people-watching is in summer, when the population mushrooms from 10,000 to 50,000, and Main Street throngs with strolling, gallery-poking visitors.
Worth a Stop: Nantucket Pharmacy, at 45 Main, scoops cones and pulls old-fashioned milkshakes from behind its soda counter.
When in Rome...Georgia, don’t miss a stroll down Broad Street. It’s a veritable case study in small-town revitalization; locals have invested millions of dollars since the hub’s precipitous decline in the 1970s, and it shows. There have been more than 120 building rehabs in the central business district, and the area’s many Victorian homes and churches have been loved back to life.
Worth a Stop: In front of the Municipal Building sits a bronze Romulus and Remus statue—the classic symbol of Rome, Italy—that an Italian governor presented to the town back in 1929.
In August 2000, Paducah began offering incentives to artists willing to relocate to downtown’s Victorian houses. It was a key step in Main Street’s comeback and helped create a thriving community built around the arts. As you stroll, look for the Floodwall Murals depicting local history and the Art a la Cart program in which artists periodically set up workstations on the sidewalk. Galleries, small independent shops, and festivals round out the Main Street experience.
Worth a Stop: The National Quilt Museum, with rotating exhibitions of contemporary and antique masterpieces, plus hands-on classes.
Greenville has made tremendous strides over the last few decades, successfully turning its Main Street area into a lively and pedestrian-friendly destination (case in point: four lanes of traffic were reduced to two lanes with free parking). Its streets are lined with coffee shops, pubs, and antique shops. And each year, from spring until mid-fall, the city hosts Main Street Fridays, a series of live music performances, featuring everything from jazz to oldies to soul.
Worth a Stop: Stop by the Upcountry History Museum to browse its collection of historical artifacts related to South Carolina’s “Upcountry” region, including the “Focus Gallery,” all curated by community groups and local organizations.
When you exit historic Hoboken Terminal, you’re caught between striking views: the steely Manhattan skyline across the Hudson and the small-town charm of Washington Street ahead. It spreads before you with outdoor café tables, old-time lampposts, boutiques, Irish pubs, and a music venue with cred, Maxwell’s. Young families and fresh college grads have flocked to the prewar brick walk-ups, changing the fabric of this once blue-color town (most famous as the birthplace of Frank Sinatra). Washington Street gets feisty at nighttime and has become infamous for hard partying around St. Patrick’s Day.
Worth a Stop: Family-run Carlo’s Bake Shop has been making cannolis and fanciful cakes since 1910. It’s now a household name thanks to the TLC reality show “Cake Boss.”
Front Street has seen all kinds of action since the early 1800s: Hawaiian royals who briefly made their capital here; tavern-hopping whalers; missionaries; and adventurers seeking their fortune in this balmy Maui town. Thanks to community efforts, it's still dominated by evocative two-story wooden buildings with wraparound balconies. Inside, many businesses now cater to tourists looking for coral necklaces, artwork, and fruity cocktails at sunset. Whale-watching tours depart in season, not far from an enormous banyan tree—and favorite photo-op—that faces the courthouse.
Worth a Stop: The Wo Hing Museum at 858 Front St., once a cultural center for Chinese plantation workers. Compare their island life with the experiences of a missionary family who lived nearby at the restored Baldwin House.