10 of the Most Picturesque Towns in New England

Just north of Wiscasset, this often overlooked, picture-perfect village is surrounded by salt marsh preserves and oyster beds. The Midcoast village’s historic brick architecture and quaint, but vibrant Main Street overlooking the harbor balances just the right dose of nostalgia with a decidedly forward-minded food scene. In the fall, Damariscotta hosts its infamous Pumpkinfest and Regatta, which includes a delightfully oddball race featuring massive 400-700 pound, hollowed-out pumpkins piloted by fearless locals who use paddles and motors to make their way down the Damariscotta River at high tide, vying for first prize at the finish line.

With its historic brick architecture, massive, well-preserved Victorian mansions, and a harbor with to-die-for views, Maine doesn’t get any more picturesque than the village of Camden. Situated in the heart of the Midcoast, the village’s working harbor is continually peppered with a steady flow of handsome sailboats, classic windjammers, and historic schooners and, to top to off, it’s surrounded by a rolling, mountainous landscape that cascades seamlessly down to the water’s edge.

A visit to Woodstock is like walking into a Robert Frost poem. You can’t get any more ridiculously, wonderfully picturesque than this quintessential Vermont town. And everything you’ve ever wanted from a visit to Vermont is right here: classic covered bridges, local cheese makers, cider mills, working farms and orchards, sugar shacks, meandering brick streets, and a town center that is straight up Norman Rockwell territory.

A classic New England harbor town, Newport’s deep red brick streets, bustling outdoor markets, old school ice cream and taffy shops, historic seaside taverns, romantic Cliff Walk, and a glut of over-the-top, Gilded Age mansions make you feel like you’ve stepped into a world equal parts Age of Innocence and Moby Dick.

Situated at the mouth of the Mystic River this historic seaport town characterized by its Colonial architecture offers the complete delusion of stepping back in time, in spite of its sizeable tourist footprint. Formerly one of Connecticut’s chief centers of the shipbuilding industry, today Mystic is probably best known for its impeccably preserved seaport, which is home to one of New England’s most impressive collections of historically significant merchant vessels, which are a hit with kids and grown-up kids alike.

This tiny Nantucket town gives visitors exactly what they are hoping to find when they plan a visit to this storied island—sweeping panoramas of the Atlantic Ocean and Sankaty Head Light, rows of classic New England saltbox houses, and delightfully overflowing gardens chock-full of beach peas and roses all enclosed in white picket fences. Don’t miss the excellent ‘Sconset Bluff Walk. It runs north along the coast from the village towards the lighthouse and is, hands down, the island’s most scenic coastal walk.

With stunning old brick streets, charming maple syrup farms, quaint storefronts, classic covered bridges, gorgeous nature preserves, art galleries, and restaurants, Keene, the darling of New Hampshire’s southwestern Monadnock Region has it all. The college town—it’s home to Keene State College—even has a white clapboard church with a soaring spire.

First settled by Europeans in 1635, this historic, seaside town has immaculate, piping red brick streets and a vibrant working harbor that delivers that quintessential, New England feel. Classic seafood shacks, charming taverns with Old World flair, and a bevy of upscale specialty boutiques housed in stunning, Federal-style architecture adds to charm of Newburyport’s historic old town district.

Most of Maine’s visitors don’t make it much farther than the Midcoast, but Down East Maine is more than worth the hike, if only to pay a visit to Eastport, a picturesque seaside town with historic architecture situated on pristine Moose Island. A world apart, Eastport prides itself on its fishing and lobstering industries, excellent local arts scene, and vibrant indigenous community. It’s also home to the infamous Old Sow, one of America’s largest tidal whirlpools. Think about the Instagram possibilities!  

Artists have flocked to Monhegan Island since the mid-19th century to relish both its isolated location and staggeringly beautiful terrain. The island’s dramatic cliffs overlook some of the most stunning coastal landscapes in Maine where puffin, seals, porpoises, and whales mingle among the bevy of smaller, rocky islands surrounding it. Artists still make the hike out to the island each summer to paint and draw en plain air, while day-trippers come to take in the quaint, saltbox architecture, imposing lighthouse, and hike the island’s many meandering, well-marked coastal trails.

Tucked between Providence and Newport, this small New England town has a lot to offer in the way of history, but Bristol’s charm lies chiefly in its breathtaking scenery and well-preserved, historic architecture, comprised of excellent examples of Colonial, 19th century, Gilded Age, and pre-war architectural styles.

On the southwestern bank of the beautiful Connecticut River lies Essex, a quaint New England town scattered with cozy inns and taverns and historical architecture that can easily—and are best—explored by foot. Probably best known as one of the towns that contributed to the fictional Stars Hollow of Gilmore Girls fame, Essex has a lot to offer in the way of small town charm, with a picture-perfect harbor, a historic steam train that tours nearby areas, and a delightfully eclectic cluster of structures flaunting architectural elements as diverse as Federal and Egyptian Revival.