The Search for the Prettiest Town

A postcard look, a tranquil setting, the balance of nature and man-made elements? Never mind a winner, just determining the rules of the game is hard enough.

In Fitzwilliam, New Hampshire, I learn the first lesson about finding the prettiest town in upcountry New England: Timing matters. Fitzwilliam might actually be the prettiest town in all of Maine, New Hampshire, and Vermont -- once they get rid of that tent on the common, the workmen finish the library addition, and the dry, rusting fountain loses the rust and gains water.

Picturing this white-steepled village in October reminds me of another, paradoxical rule: You can't rely on timing, such as autumn foliage. No, the truly pretty is pretty even on a bad leaf day.

Fitzwilliam is one of 21 towns on a list I have compiled from magazines and guidebooks, tourist boards and film offices, websites and road maps, friends and strangers, and my own experience. I eventually will visit 39 communities over six consecutive days and five nights. As I drive through town number two, Jaffrey, New Hampshire, a white-steepled church across from a lush

garden is canceled out by an auto-body shop and a dumpy house flying a Confederate flag. In Harrisville, also in the Monadnock region of New Hampshire, I find mill buildings, a general store on a hill, a pleasant pond, but no visual center.

Three towns, three disappointments. Perhaps wise words can inform my search. "Pretty as a picture" is no help; a picture can be shrewdly framed or generously interpreted. "Pretty is as pretty does" sounds noble -- but how does a town do pretty? "Beauty is in the eye of the beholder" is that great rationalizer, giving us such "beauty" modifiers as "stark," "terrible," and "unexpected."

Beauty is easy, compared with pretty. Someone could make a case for the light playing off a dumpster lid as oddly beautiful, but never pretty.

I'm already feeling pressure as the Arbiter of Aesthetics when I drive past the gray-stone cemetery, white-steepled church, and town common bandstand leading to the commercial center of Hancock, New Hampshire. As I leave a cafe, a butterfly hovers as if to greet me, then -- clearly showing off -- darts among the flowers in the garden that borders the entry walkway. This, I decide, must be the Chamber of Commerce butterfly.

Hancock has more than just church, town offices, and library -- nothing, of course, against God, country, and literacy. Even when a truck rumbles through, it's a friendly and fleeting rumble. At the Barn of Hancock Village, an antiques and art shop, Ray Pierce knows that pretty doesn't happen by accident. "We're fighting hard to retain the character and not have the physical things change," he says.

Ideally, the natural and the man-made harmonize: Below some of the Barn's wooden beams, past a candle and a Princess Feather lamp, a crowd of small pasture roses seems about to enter an open side door. I head out of town, appreciating Ray Pierce's definition of pretty towns as "small, well-maintained areas with that peace and calm you look for."

So pretty is more than a postcard look -- it's an inhabited feeling. It does matter how they're inhabited. For my lasting impression of white-steepled Francestown is of a woman in a Jeep, cigarette in mouth, with too much year-round body squeezed into too little summer clothing.

On my way to Damariscotta, Maine, past a New Boston, New Hampshire, gazebo that loses its appeal on third look (for pretty should be a lasting thing), I read, at 8:47 p.m., this sign:

I'm only a few miles from Damariscotta, but how can I leave Wiscasset now?

The next morning, I learn that Wiscasset has water views, an in-town castle (Castle Tucker), the Sunken Garden -- and an overwhelming aural besmirchment. "The greatest detriment to Wiscasset is that Route 1 runs through the downtown," says Sharon Mrozinski of the Marston House antiques shop and bed-and-breakfast. "In the late 18th century, you could walk from boat deck to boat deck across the river." In the early 21st century, you can walk the downtown on the roofs of cars.

She sends me to Sheepscot Village, part of Newcastle, a town on my list. Once I'm in Sheepscot Bay, no matter where I turn, I see and feel that "peace and calm you look for." Light dances off the water. Birdsong harmonizes with the light. Even the power poles seem one with nature. The water is empty of boats, and the houses hardly seem inhabited.

Is it pretty? Raymond Chandler once wrote of a woman so comely she'd make a bishop kick a hole in a stained-glass window. Sheepscot is so pretty that I'd put an unshod foot through the nearest store window. If I could find one. For while this place is beyond pretty, is it a town?

As you enter Damariscotta, a water view soon gives way to gas stations. You do need gas to drive Route 1, which takes me through Rockland on my way to Rockport, leaving Route 1 to wind past shaded homes and then a golf course (that shotgun marriage of the natural and the man-made).

Of Camden, the most-mentioned town in my pre-trip research, Laura Amey, owner of a Camden cafe called Ortolan, says, "I think it's beautiful. But this whole Route 1 section sort of soils the town." On cue, a truck rumbles by. I wait. Then I ask her what makes a pretty town.

"Landscape, the general pace and attitude of the people, and some sort of focal point," she says, suggesting Castine (already on my list) and Pemaquid Point in Bristol.

The grounds of the town library offer a postcard-worthy harbor view, while inside the library a publication marking the dedication of the Centennial Wing excerpts area native Edna St. Vincent Millay's poem "Renascence," which begins:

All I could see from where I stood
Was three long mountains and a wood;
I turned and looked the other way,
And saw three islands in a bay.

Despite the iambic tetrameter, I drive up Mount Battie, which served as the poet's perspective. The view is gorgeous, more panoramic than from the library. But unless you are a pilot or a bird, improbable aerial views are a cheat.

Castine is, mercifully, miles from Route 1, and after checking into an inn, I run along Water Street and glimpse sailboats, water, and trees, then enter a cemetery as the 7:15 sun hangs large and low. And when the late-day light catches the white gravestones, illuminating them in subtle contrast to the dark water beyond, I realize that cemeteries can make for a crowded-yet-quiet pretty town.

A guy in the Dennett's Wharf restaurant suggests I try Pemaquid Point, plus Manchester and Shelburne in Vermont, then adds, "Camden by the view, Rockland by the smell."

After breakfast the next day, I discover Dice Head, where a narrow footpath winds downhill through colorful wildflowers, carrying me over rocky patches and exposed tree roots, under the songs of anonymous birds, through a mix of trees and light and shade, and into a cooling breeze to a steep drop where the water laps behind the thick cover of trees. All along, I am pulled down the path by gravity and uplifted by the promise of changing beauty.

Castine will be a tough act to follow, and the prettiest sight in Blue Hill, Maine, is the ocean view from the town park. Heading west, I come to the small city of Hallowell, where brick buildings in reds and painted creams background flowered window boxes, and the Kennebec River runs on one side, while on the other the streets rise up into rural environs.

Hallowell's mix of a colorful, gritty-pretty downtown (no monochromatic white-steepled village here) and natural surroundings makes it a Prettiest Town contender. But "contender" won't satisfy these natives. At Berry & Berry Floral, Jennifer Brann cites Hallowell's physical beauty and that everybody's friendly.

Nancy McGinnis, the library director, points out that building's hand-carved moldings and stained-glass windows, and all but shackles me to the card catalog when I try to leave. Tim Plumer, proprietor of DukinFields Antiques, says of his town: "There's wonderful architecture, and no neon lights. We're a little town, a little family. And if you find someone who tells you their town is better, tell them I said they're full of it."

In Slates restaurant, a dark-wood space with tin ceilings and brick walls, a guy named Pete suggests I head to Pemaquid Point -- his retreat for solace. (How can he find solace, I wonder, when so many people keep telling me to go there?) "Waldoboro," offers a man who could be US Senator Sam Ervin's double (before Ervin died). "Lincolnville," pipes up a fellow in a cap, bushy beard, and long ponytail. "You can build a case that Phillipsville is it," says Senator Sam. They ask what other people suggest.

"Camden," I say.

"Camden," says a woman named Peggy, "has gotten a big head."

When Senator Sam adds Alfred, Maine, to the list, I know I'd better pull myself from Hallowell's big embrace or I'll never finish my odyssey.

I head toward Kents Hill (nice views of rolling hills, but not much else), to the rhyming town of Wayne, Maine, which serves as a smaller, quieter counterpoint to Hallowell. Just past Androscoggin Lake sit a pottery shop, a walk-up eatery, and a general store, behind which three 18-year-old guys stand shirtless on a wooden bridge above the Mill Stream, then jump into water that rushes over a dam and rocks, between tree-lined banks, and toward a darkening distance.

The next morning, I check out four White Mountain towns in New Hampshire. Bartlett seems depressed. Glen can say that a river runs through it. The prettiest thing about Intervale may be its name. Jackson proves that a covered bridge (and an oppressive tourist-town feel) does not a pretty town make.

My route to Craftsbury Common, Vermont -- my journey's northernmost point -- takes me through the valley town of Gorham, New Hampshire, which is certifiably backdrop-pretty. Jefferson starts out view-a-licious, then deteriorates into a golf course, a beat-up town hall, and Santa's Village. Lancaster offers a black-and-white steeple, and Danville, Vermont, some nice planted flowers.

By now I've entered, evaluated, and exited so many towns that I feel jaded, wanting a place to buckle my knees with prettiness. Craftsbury Common doesn't do it, its white-fenced common marred by a huge neighboring black satellite dish. But from Strong Road I see trees and fields give way to a distant silo amid rolling hills and acres of sky. Now I know that the name should be Craftsbury Vista, trading alliteration for truth in advertising.

The Vermont town of Hyde Park is marred by a cellphone tower (the white steeple of our future?), and I end day four in Shelburne, reputedly a once-lovely town that has become a built-up suburb of Burlington. It does offer views the next morning of Lake Champlain and green hills on my way to the small city of Vergennes.

"I like Vergennes," says Tara Vaughan-Hughes from her cafe called Eat Good Food, "but I wouldn't say it's the prettiest town." At the Black Sheep Bistro, the suggestions are somewhere near Ellsworth in Maine and Hanover, New Hampshire.

But I have more of Vermont to see, and Chelsea's virtual you-can't-get-there-from-here location hints at a connection between elusiveness and prettiness. On my way, I discover Bristol, Vermont, a scaled-down Hallowell with a northeast slope of trees seeming to touch downtown itself.

In Warren, when a white-haired man in a sherbet-colored polo shirt walks out of the Pitcher Inn (entrees, $24-$34), I am reminded of the connection between prettiness and prosperity. Money helps preserve a place's appeal, which lures those willing to pay a pretty sum. Warren even has an eccentrically attractive bus stop -- a grounded cupola (bell still attached) that apparently belonged to the neighboring, decapitated Warren United Church. While Warren doesn't feel friendly -- I recall the warmth of such earthier spots as Hallowell, compared with the coolness of sherbet towns -- it stylishly blends the man-made and the natural.

And Chelsea? An attractive inn, surrounding hills, and a depressed feel. A covered bridge in Tunbridge gives way to South Royalton's beckoning spire of yellow with reddish-brown trim, and it's a short trip to and through the stiffly collegiate Hanover, New Hampshire, home of Dartmouth College, where the prettiest sights are the people. I gladly return to a Vermont town that my wife, daughter, and I have visited six times in the past four years, which makes it hard to look at Woodstock with a fresh eye. But how objective is pretty? On my walk the next morning, the green expanses of the Billings Farm are soon refuted by the columns that stand sentry in front of homes, reminding me that Woodstock is another sherbet town -- pretty but cool.

It's day six, and my search is winding down. Chester is brightened by colorful Victorian houses and a meandering brook. Grafton seems a compromise between the simplicity of Warren and the visual opulence of Woodstock.

I end my search in Washington, in southern New Hampshire, where I began six days before, now knowing that the prettiest sherbet town is Woodstock, the most gritty-pretty, Hallowell. Among quiet towns, Wayne is the prettiest friendly one, Warren the prettiest aloof one. The prettiest townless town is Newcastle, and the prettiest downtown is Hancock. The prettiest distant views come from Craftsbury Common (but not from the common), while the prettiest in-town views are in Castine.

And the fairest of them all? Come on. That's pretty impossible, don't you think?

David Maloof is a writer who lives in Belchertown.