Danita Delimont / Alamy

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

Nantucket, MA

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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.

—Adrien Glover

America’s Greatest Main Streets

Nantucket, MA

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.

—Adrien Glover

Danita Delimont / Alamy

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

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