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. Galena, IL (Photo: Judy Lange)
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., and it’s well worth driving the extra few miles to see what Main Street is up ahead. Let us point you in the right direction.
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.
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)
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.
Worth a Stop: Fuel up at Mud Street Café on South Main Street, then drive three miles into the forest for architect E. Fay Jones’s majestic Thorncrown Chapel, built with huge glass panels.
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.
See more of America's Greatest Main Streets
Galena, IL (Photo: Judy Lange)