Issues → May/June 2008 → Interact → 10 Things to Do →

A Sampler of New England's Prettiest Towns

Kittery, Marblehead, Harrisville, Grafton, etc.

by Janice Brand

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Photograph of Marblehead, MA
Submitted by Robert Dennis

Photograph of Grafton, VT
Submitted by Alexander Watt

Photograph of Wethersfield, CT
Submitted by Walter Michalik

Photograph of Harrisville, NH
Submitted by David Henry

Photograph of Sugar Hill, NH
Submitted by Leslie S. Grima

For as long as I've been driving around New England, I've never run out of towns 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 the prettiest towns in New England.

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. The market is Frisbee's, which claims, at 170 years, to be the oldest family-owned grocery store in North America. On the right you won't miss the sign for Cap'n Simeon's Galley, a restaurant overlooking Portsmouth harbor that serves a very good lobster roll and grilled fish amid a relentless nautical decor.

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.

After lunch, take the turn onto Gerrish Island and visit Fort Foster. I'm no great fan of fortifications, but this one has a view of the distant Isles of Shoals (the far lighthouse is on White Island; the closer one is Whaleback Light at the mouth of the Piscataqua River) and rocky coast to clamber.

Kingfield, Maine

Most people make the trek to Kingfield, in Maine's western mountains, to go skiing at its big neighbor, Sugarloaf/USA. I can think of at least two other good reasons to visit.

Named for William King, its founder and Maine's first governor, Kingfield has matured on the ski business, but it was born on lumber mills. Main Street looks as if it would be comfortable in the Old West, its clapboard stores bellying up to the road. The Herbert Hotel, a Victorian whimsy built in 1918, has been restored with a Gilded Age feeling and acts as command center in town. For dinner, cognoscenti move to One Stanley Avenue, which prides itself on using fresh, local ingredients. It is known as one of the best restaurants in the state.