11 Prettiest Small Towns In New England
The most painted building in the world is a red fishing shack on a granite wharf in Rockport, Massachusetts, and the one standing there now is a 1978 replica of the one a blizzard knocked into the harbor. That is New England in miniature: a place so committed to how it looks that it rebuilt a shed to exact specification. These eleven towns are the prettiest in the six states, and none of them holds more than about 15,000 people. Come in late September or October if you can, when the hardwoods turn and the whole region earns its reputation in about three weeks.
Stowe, Vermont
Mount Mansfield is the highest point in Vermont at 4,393 feet, and Stowe sits at the base of it in the Green Mountains. Stowe Mountain Resort runs the winter, but the gondola keeps turning through foliage season, and the trails and climbing wall open once the snow goes. The Vermont Ski and Snowboard Museum stays open year-round with rotating exhibits, including past shows on the state's lost ski areas and on Scott Lenhardt's artwork for Burton snowboards.
Vermont produces more maple syrup than any other state, by a wide margin, so leaving without any would be an act of will. Stowe Maple Products sits on Route 100 and sells the syrup along with maple cream and maple caramels. In the village, The Country Store on Main handles the general-store side of things: cookware, table linens, holiday decorations. Roughly 5,000 people live in Stowe year-round, and several times that arrive on a good winter weekend.
Rockport, Massachusetts
On July 8, 1856, a woman named Hannah Jumper led about two hundred townspeople through Rockport with hatchets and destroyed every barrel of liquor they could find. The town voted itself dry immediately afterward and stayed that way for nearly 150 years, until a 2005 town-meeting vote finally let restaurants pour. Some places still do not, out of habit.
Rockport sits at the tip of Cape Ann, about 40 miles northeast of Boston, and it has been an artists' colony for well over a century. Motif Number 1 is the reason: a red lobster shack on Bradley Wharf that painters have rendered so many times it acquired a nickname from the instruction "paint motif number one." Bearskin Neck runs out into the harbor as a narrow lane of galleries and chowder counters. North of town, Halibut Point State Park is a flooded granite quarry on the headland, with the Atlantic on three sides.
Nantucket, Massachusetts
Whaling money froze Nantucket in place. The industry collapsed in the 1800s, nobody had the funds to rebuild, and the result is a cobblestoned town of pre-Civil War buildings kept largely intact. The Jethro Coffin House, built in 1686 on Sunset Hill, is the oldest structure on the island and open for tours, with a reconstructed 1700s kitchen garden out back. Down Main Street, the 1846 Hadwen House is the Greek Revival showpiece, now a museum with a Victorian garden.
The island lies roughly 30 miles south of Cape Cod, reachable by ferry or a short flight, and the isolation is the point. 40th Pole Beach on the north shore has warm, shallow water and soft sand, which makes it the family choice. Out at the northern tip, Great Point Lighthouse has been rebuilt twice since the original went up in 1784, most recently in 1986 after a storm took the previous tower down.
Westerly, Rhode Island
The Flying Horse Carousel at Watch Hill is thought to date to around 1876, which makes it one of the oldest in the country, and it still works the way it did then: the horses hang from chains rather than standing on poles, so they swing outward as the ride picks up speed. It is a National Historic Landmark, and adults are not allowed to ride.
Westerly was first settled in 1661 and sits right on the Connecticut line. Ocean House, the Victorian pile above Watch Hill beach, holds both a AAA Five Diamond and a Forbes Five-Star rating, and the stretch of shoreline it overlooks includes the promontory where Taylor Swift's house sits. Downtown, Perks and Corks does coffee by day and cocktails at night in the same dim room. For the older history, the Babcock-Smith House is a 1734 Georgian with its original cooking fireplace and a staircase worth the visit on its own.
Essex, Connecticut
The Griswold Inn has been taking guests since 1776, which puts it among the oldest continuously operating inns in the country, and it is still the center of gravity in Essex. The village hugs the Connecticut River with rows of Federal and Colonial houses that have been maintained rather than restored, which is a different and better thing.
The Essex Steam Train and Riverboat is the standard outing and it earns the two and a half hours: a vintage train up the valley, then a boat past Selden Neck State Park and the villages of Deep River and Chester. The dinner train adds four courses to the same route after dark. Walking tours cover the downtown, the River View Cemetery, and the neighboring village of Centerbrook.
Woodstock, Vermont
Vermont has around 100 covered bridges and Woodstock has one right in the village, which is why the Middle Covered Bridge turns up in so many photographs. The town of roughly 3,000 fills up every October for leaf season, and the walk up Mount Tom from the green delivers the panorama people drive four hours for.
Billings Farm and Museum is a short walk from the center and still a working dairy operation. You can watch the milking, tour the 1890 farmhouse, and meet the sheep, goats, chickens, steers, and horses, and the calendar runs special events through the year including a Harvest Celebration and one built entirely around maple. The Apples and Crafts Fair lands in October, in the thick of the color.
Washington, Connecticut
Amy Sherman-Palladino stayed at the Mayflower Inn here and came away with Stars Hollow, which is why Gilmore Girls fans keep turning up in a Litchfield County town of about 3,500 people. The reality holds up. Marty's Cafe handles the coffee, and The Hickory Stick Bookshop next door has been selling books since 1948, with signings, poetry readings, and a monthly club.
Averill Farm has been in the same family since 1746, which makes it one of the oldest continuously family-run farms in Connecticut. It opens from mid-August to the end of December for apple picking, cider donuts, pies, pumpkins, and jams. Hollister House Garden is the other stop, a formal English-style garden laid out in rooms across several acres, open to visitors in the warmer months.
Camden, Maine
Camden advertises itself as the place where the mountains meet the sea, and for once the slogan is literal. Mount Battie rises directly behind the harbor inside Camden Hills State Park, and you can drive or walk to the stone tower on top. Edna St. Vincent Millay grew up here and wrote "Renascence" after climbing it, which is a rare case of a view producing a poem you can still read.
Down at sea level, the harbor holds one of the last working windjammer fleets in the country. These are tall-masted schooners, several of them National Historic Landmarks, and they take passengers out on multi-day sails through Penobscot Bay between late spring and October. The town itself runs to about 5,000 people, with a compact brick downtown and a waterfall dropping into the harbor at the head of the bay.
Bar Harbor, Maine
Bar Harbor is the front door to Acadia National Park, which packs about 158 miles of hiking trails and 72 miles of motor and carriage roads onto Mount Desert Island. The carriage roads are the John D. Rockefeller Jr. legacy, crushed stone and stone-faced bridges, closed to cars and ideal on a bike.
Cadillac Mountain is the summit everyone wants, and the sunrise claim needs a caveat: it is the first place in the country to see the sun only between roughly early October and early March, when the geometry works out. Summit road access requires a vehicle reservation in the busy season, so book it. Back in town, The Terrace Grille does the chowder and steamed lobster, and Havana runs a seasonal menu that puts Latin technique on Maine seafood.
Jackson, New Hampshire
You enter Jackson through a covered bridge. The Honeymoon Bridge has carried traffic over the Ellis River since 1876, and the village on the other side holds fewer than a thousand people in a bowl of the White Mountains. Jackson Falls runs right along the road above town, a long series of ledges and pools that people picnic beside all summer.
In winter the Jackson Ski Touring Foundation grooms one of the largest cross-country networks in the East, with trails running out of the village center and across private land the town negotiated access to decades ago. Wildcat and Black Mountain handle the downhill. Autumn is the busiest stretch, when Route 16 through Pinkham Notch fills with cars and the village turns the color of the postcards.
Peterborough, New Hampshire
Thornton Wilder wrote Our Town at the MacDowell artists' residency here, and Peterborough is generally taken as the model for Grover's Corners. The town of about 6,400 sits on the Contoocook River under Mount Monadnock, and it has been drawing artists since MacDowell opened in 1907. The Peterborough Players have staged professional theater every summer since 1933.
The Peterborough Diner has been serving since 1949 out of a genuine dining car, and the pancakes and egg sandwiches are the reason to go rather than the decor, which is a bonus. Sweet Macaron does the French version a few doors along, in flavors that range well past vanilla. Gary Shepard Fine Art shows landscape work drawn from the country immediately outside the door.
Picking Between Them
Prettiness in New England splits into two kinds, and knowing which you want saves a bad trip. The coastal towns, Rockport, Nantucket, Camden, Bar Harbor, and Westerly, peak in summer and hold on through September, and their appeal is granite, water, and boats. The inland ones, Stowe, Woodstock, Washington, Jackson, and Peterborough, are foliage towns, and they are at their best for a two or three week window in October that shifts north to south and moves every year. Essex splits the difference on the river. The other practical note is that several of these places have more visitors than residents in season: Nantucket's population multiplies several times over in July, and Woodstock's green is standing room only on a good October Saturday. The shoulder weeks in early June and late September get you the same towns with room to park.
