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Top 9 Picturesque Towns of New England

| North America, Top Lists, United States

Top 9 Picturesque Towns of New England

Nowhere does Americana quite like New England. Wood-shingled houses are decorated with painted buoys and plump hydrangea bushes. Children lick ice cream cones while their parents chase behind them in Nantucket Reds. Leafy Main Streets are lined with historic storefronts and capped with a white steeple. In the winter months, Christmas lights set chilly streets aglow and ski resorts burst to life. No matter the season, there’s seafood to be eaten. Some of the most delectable oysters, clams and – of course – lobster come from these waters.

With a winning combination of charm and clam chowder, New England is always a welcome escape. Here are our top nine picturesque towns of New England.

Provincetown, Massachusetts

Perched on the very tip of Cape Cod, Provincetown is a world of its own. The LGBT-friendly beach town is a haven for artists, designers and musicians. With such a creative populace, the fun-loving community has built art galleries, designer shops and excellent bars and restaurants. In addition, Provincetown is home to a thriving theater scene, with big Broadway names often stopping by for summertimes performances. Strolling through Provincetown is always an adventure, with performers donning colorful costumes, shops selling unique wares and an undeniable buzz of energy pulsing through the streets. Many summer weeks in Provincetown are themed, so check the official tourism website before planning a trip.

Edgartown on Martha’s Vineyard Massachusetts

Martha’s Vineyard, set just off the coast of Cape Cod, is known for its natural beauty, iconic New England charm and extravagant estates. While the island is rather small – just 96 square miles – there are beaches to suit all sorts, from calm, shallow waters to livelier surf for wave-catchers. Those who love a long walk should visit Aquinnah Beach, famous for its vibrant cliffs marbled with multicolored natural clay. When you’ve had your fill of beach time, head to the delightful shops and welcoming restaurants that line the streets in Edgartown. Keep your eyes peeled, as the Vineyard is a popular destination for writers, artists and celebrities. Hillary and Bill Clinton, David Letterman and Chelsea Handler are all said to be frequent visitors.

Walk along Aquinnah Beach, famous for its vibrant cliffs marbled with multicoloured natural clay.

Walk along Aquinnah Beach, famous for its vibrant cliffs marbled with multicoloured natural clay.

New Castle, New Hampshire 

The town of New Castle is located entirely on islands. One of New Hampshire’s smallest towns, New Castle has a storied history that dates back to 1623. Today, the town is best known for its beautiful waterfront and destination-worthy hotel, Wentworth by the Sea. Great Island Common is New Castle’s loveliest green space, with plenty of spots for picnicking and a small, peaceful beach. New Castle stands out among New England’s waterfront towns for its truly local feel. Set alongside Portsmouth, it’s easy to visit Portsmouth’s tourist attractions like Strawberry Banke before retreating to your peaceful oasis at day’s end.

Littleton, New Hampshire

On the banks of the Ammonoosuc River, Littleton is a postcard-perfect town with many natural wonders on its doorstep. With so much beauty outside, hiking is a common pastime in Littleton. Trails run alongside the bubbling river, through blueberry patches and on to swimming holes. For those seeking more strenuous trails, the White Mountain National Forest is just to the southeast of Littleton. Venture into the forest for a stroll through the greenery or an advanced climb above the tree line. Back in town, stop by Schilling Beer Co. to try their European-style beers that are brewed in-house. Especially after a long hike, their brews pair perfectly with a plate of New England-made cheeses and charcuterie.

With so much beauty outside, hiking is a common pastime in Littleton. Trails run alongside the bubbling river, through blueberry patches and on to swimming holes.

Newport, Rhode Island

A longtime refuge for the well-heeled set, Newport is home to dazzling historic mansions that are open to visitors. A tour of Newport’s historic estates takes guests through a veritable “ who’s who” of the 19th-century’s biggest industry magnates. Among the most impressive homes is the Breakers, built by Cornelius Vanderbilt II in the style of a Genoese palace. Another contender is Rough Point, constructed from 1887 to 1892 by Frederick W Vanderbilt. While today’s aesthetic is less extravagant, Newport remains a posh destination for the yachting set. Thankfully, there are many less pricey pursuits to enjoy, like walking on the white sand beach, kayaking along the rocky coast and slurping oysters fresh from the sea.

Enjoy kayaking opportunities in the scenic Newport

Enjoy kayaking opportunities in the scenic Newport

Lenox, Massachusetts 

The cultural capital of the Berkshires, Lenox is home to world-class art galleries, farm-to-table restaurants and quirky shops and bookstores. As a hub for intellectuals, Lenox frequently hosts prestigious lectures, workshops and theater productions. Since 1937, the Boston Symphony Orchestra has made their summertime home at Lenox’s Tanglewood Music Center, drawing orchestra fans from throughout the country. While summer is an ideal time for music lovers, Lenox is particularly scenic in the autumn, when fall colors are on full display and apple orchards celebrate the harvest with lively festivals. Spirituality seekers can stop into Kripalu Center for Yoga and Health for a yoga class or register for a week-long meditation retreat.

Rockport, Massachusetts

Set on the tip of Cape Ann, Rockport and neighbouring Gloucester were once thriving fishing villages. While Gloucester’s fishing industry remains, Rockport’s story took an artsier turn. Rockport’s rugged coastline and quirky buildings have drawn painters for decades. The town’s most iconic scene is a red fishing shack called “Motif #1.” The seaside shack, destroyed in a 1978 blizzard and rebuilt, is often cited as the most frequently painted building in the United States. The main drag that leads to the waterfront, Bearskin Neck, is lined with unique shops and galleries selling works by local artists. After a day of shopping, duck into one of the seaside taverns for a decadent plate of fried seafood fresh off the boats bobbing in Gloucester Harbour.

Rockport’s rugged coastline and quirky buildings have drawn painters for decades

Rockport’s rugged coastline and quirky buildings have drawn painters for decade.

Kennebunkport, Maine 

Kennebunkport is coastal Maine at its most idyllic. Dock Square, the buzzing town center, is filled with antique shops, general stores and interior design boutiques housed in buildings that are mostly unchanged since the 1800s. For more shopping and strolling, take the bridge over the Kennebunk River into neighboring Kennebunk. On the bridge, stop into the Clam Shack, one of the most iconic lobster roll outposts in Maine, to try Maine’s most beloved delicacy. Summer marks the height of activity, but the towns are just as atmospheric in the spring and fall when the air is crisp and the crowds are smaller. The Kennebunks come alive again at Christmastime, with a tree lighting and a Christmas market often called one of the best in the country.

Portsmouth, New Hampshire 

Portsmouth is one of America’s oldest settlements, with the impressive colonial architecture to show for it. However, Portsmouth is not all about history. Today, the riverside city is a hub of youthful energy, known for its hopping craft brewery scene and innovative restaurants. After tasting the local IPAs, explore Portsmouth’s many museums and historic homes. A highlight is Strawbery Banke, a living history museum comprised of 37 buildings on a 17th-century settlement. Another home worth visiting is the Wentworth Gardner House, a stunning Georgian house built by wealthy residents in 1760. On Saturdays in the warmer months, the Portsmouth Farmers’ Market is the place to be for fresh produce, artisan handicrafts and delicious street food.