New England's Prettiest Towns | A Sampler of Picture-Perfect Villages
For as long as I’ve been driving around looking for New England’s prettiest towns, I’ve never run out of villages that look just like their postcards. A white-steepled church fronts the town green, which is bordered by black-shuttered white clapboard houses; or squat Capes clad in weather-beaten shingles match the shacks where the lobstermen work down by the harbor.
Sometimes a friend steers me toward one of these towns. More often I’m lost, and the town is the reward for driving in circles or down endless two-lane roads.
Everyone’s definition of a pretty town probably differs, but I look for a sense of time passed by, a preservation of the past, and a very real present. Qualifying towns don’t have to lie far off the beaten path; they may be under your nose. And there should be somewhere to eat. I’m not being romantic when I say I’ve discovered most of these places when lost. I’ve usually been quite lost — and quite hungry.
Here, then, is a highly subjective list of my contenders for New England’s prettiest towns.
Kittery Point, Maine
If you think that Kittery is just the mall-to-mall strip of outlets along Route 1, you have a very pleasant surprise waiting. Make a detour on Route 103 toward Kittery Point, the oldest town in Maine, first settled in 1623.
The road rolls along to the sea, passing through sparsely populated countryside. Where there’s a sharp turn, look closely for the grand (and private) Lady Pepperrell House, built in 1760. Across the street is the First Congregational Church, built in 1730.
Farther along, the Fort McClary Memorial is the remnants of a fort named for a local soldier who died at the Battle of Bunker Hill. A cluster of houses, a post office, a church, and a market describe the town.
But if you want lobster outdoors in the Maine tradition, continue on Pepperrell Road and look for the sign for Chauncey Creek Lobster Pier, which will direct you down narrow Chauncey Creek Road. On your right is the Lobster Pier. With a view of forested Gerrish Island from one of the brightly painted picnic tables on the deck and perhaps a cooling breeze coming upstream, this feels miles from anywhere. The Lobster Pier serves lobster — the lobster rolls come doused with paprika on an untoasted bun — clams, and steamed mussels in wine and garlic. You have to bring your own wine or beer.