Image: Union, Wash.
John Marshall Www.johnmarshallph
“There is something breathtaking about the way the Hood Canal winds its way through hills filled with thousands of evergreens,” says Erin Anderson of Union, on the Kitsap Peninsula, in Washington's Puget Sound.
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updated 10/19/2009 11:44:57 AM ET 2009-10-19T15:44:57

As the sun casts its autumnal glow on thousands of picturesque U.S. cities and towns, it's the perfect time to recognize the proverbial winners of the country's civic-beauty contest. Some you may recall from last year, others are brand sparkling new.

Like all such pageants, this is a subjective one—but we've received help from several experts with keen eyes for architecture, aesthetics, and small-town charm. This year's pretty-town pickers include Salt Lake City-based architectural photographer Alan Blakely; residential designer Erin Anderson; and painter John Vander Stelt.

We left the definition of “pretty” up to the judges themselves. Photographer Blakely said he was drawn to places that were "fairly pure, architecturally—without a lot of commissioned residential architecture, but rather, structures built by private builders or the occupants themselves."

Among Blakely's picks is the southwest Montana enclave of Dillon. He says its conventional main street, independently owned businesses (and absence of big-box stores) contribute to its "nice flavor." He also appreciates Dillon's historical significance ("It's central to the Lewis and Clark story.") and its proximity to world-class fly-fishing.

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Greg Melville, co-author of "101 Best Outdoor Towns", explains the criteria he used in making his choices: “Each of these places is among the most picturesque (in the country)—whether it's the natural surroundings, the architecture, or more likely a combination of the two.”

Melville's list includes the Chesapeake Bay-side town of Annapolis, Md., which he says "is somehow able to maintain ties to its historic colonial and maritime past without seeming hokey," adding, it is "perhaps the East's most romantic town."

For residential designer Erin Anderson, architecture and city-planning factored in to her decisions, but some of her picks made the cut by their sheer beauty of their surroundings. Describing the small town of Union, Wash., located on the Puget Sound, Anderson says, "There is something breathtaking about the way the Hood Canal winds its way through hills filled with thousands of evergreens."

Painter John Vander Stelt brought an artistic frame to his selections, noting that, in one of his picks, Guttenberg, Iowa, "The local city park hugs the shoreline and is reminiscent of Seurat's painting 'A Sunday Afternoon on the Island of La Grande Jatte.'"

Image: Historic Battery Point Lighthouse
Gunter Marx  /  Alamy
Alan Blakely describes Crescent City, Calif., about 20 miles south of the Oregon border, as a “quiet town, with big empty beaches, and big stands of redwoods, surrounding it. At 5 a.m. the fisherman head out from the and bring back excellent seafood.”
In a couple of cases, historical richness added extra appeal to a town's prettiness. Two of our judges, Vander Stelt and Blakely, separately picked towns that are listed—in their entirety—on the National Historic Register. Vander Stelt chose the rugged South Dakota outpost of Deadwood, an erstwhile hideout for Gold Rush fortune-seekers and outlaws, and Blakely listed the central-Utah town of Spring City, originally a Mormon settlement and now a magnet for artists.

America's Prettiest Towns provides a closer look at our experts' diverse list of comely communities.

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