A Sampler of New England's Prettiest Towns
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.
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I’d love to see you include Litchfield, CT – it has the traditional town green, a white spired Congregational Church, and many original well preserved homes from the 1600′s and 1700′s.
I checked the website for Hilltop Inn — their price list is from 2005-2006. It would be nice to think the rates haven’t gone up….
Loved this article. I visited Harrisville on your recommendation and fell in love with the town. Spent a bit of time at Harrisville Designs…and left with gorgeous yarn! I will be trying to get to these little towns in the next year!
I lived in Harrisville in the mid 1980′s. It is everything you say and more. A beautiful village off the beaten path.
Sugar Hill is best seen in early June, when alll the Lupine are in bloom. As you wind through the village, you see fields of Purple Lupine everywhere. It is magnificent!
“Protected from macadam, Grafton is a gem of the early 1800s. True, it’s had a little help in looking so pristine and all from the wealthy Windham Foundation, which bought and restored the entire town. But there’s no denying it’s pretty.”
Just wanted to throw out there that the Windham Foundation does not own the town of Grafton in any way. While they helped restore many buildings in the village, and own The Old Tavern as well as Grafton Village Cheese, the town itself is a regular town with 600 residents. And it is a beautiful town that has a lot to offer visitors! You can find out more on the Foundation at windham-foundation.org. It’s a nonprofit dedicated to promoting Vt.’s rural communities.