America’s Greatest Main Streets

Begin Slideshow
© Judy Lange

Cheers to these small towns for great Main Streets, where you can admire architecture, sample the local flavor, and find a lost America.

Galena, IL

1 of 26

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.

—Wayne Curtis

America’s Greatest Main Streets

Galena, IL

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.

—Wayne Curtis

© Judy Lange

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.

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.

—Wayne Curtis

Did you enjoy this article?

Share it.

Explore More