7 of the Prettiest Towns in the Northeast

When it comes to cute towns, many travelers would argue that the Northeast takes the cake. Blending well-preserved architecture, irresistible charm, deep histories, and beautiful backdrops of rolling hills, winding rivers, and rocky coastlines, many towns in this corner of the U.S. are straight out of a storybook. The following towns are some of the prettiest in the Northeast — and the entire country.

Manchester-by-the-Sea, Massachusetts

Situated north of Boston on the North Shore, this former fishing community was first settled in 1629, and nearly 400 years later, it’s still known for its history and scenic beauty. By the mid-19th century, Manchester-by-the-Sea evolved into an elite resort destination for wealthy Bay Staters trying to escape the summer heat. 

Today, the influx of wealth that went into the town is still apparent, in structures including the 1823 Abigail Hooper Trask House (now the town museum), an 1887 Classic Revival library, and a 39-acre historic district and village center. The town also lives up to its name with one of the prettiest beaches in New England, Singing Beach, which was named for its pristine — and audibly squeaky — sand.

Little Compton, Rhode Island

Though it’s located just across the Sakonnet River from bustling Aquidneck Island, Little Compton feels worlds away. This sleepy coastal town is home to miles of surrounding farmland and plenty of fascinating history, with centuries-old stone walls that meander through town and were once used to mark property lines. 

The town’s historic architecture has all the charm travelers have come to expect from New England. That’s especially true of the Wilbor House — built in 1690 and open for tours through the historical society — and the Friends Meeting House, a traditional Quaker structure from the early 19th century. The town is also known for Sakonnet Vineyard, the oldest vineyard in New England, and a well-preserved coastline, which can be explored at Goosewing Beach.

Clinton, New Jersey

Much of the beauty of Clinton can be attributed to the South Branch Raritan River, where the town’s historic gristmill was built in 1810. Thanks to the mill’s success, the town flourished, resulting in the construction of Federal, Italianate, and Victorian homes to accommodate a growing population. 

Today, more than 200 properties built between 1810 and 1930 still stand, which earned Clinton a listing on the National Register of Historic Places. After visiting the Red Mill Museum Village and admiring the town’s historic architecture, stroll through Clinton’s quaint downtown, which features artisan shops, boutiques, and cafes, or check out the Hunterdon Art Museum, a contemporary museum housed in a historic mill.

Woodstock, Vermont

Settled in 1761, Woodstock is what’s known as a “shire” town. Although that just means it holds the county seat, one could also argue that it retains the charm and beauty associated with the hobbits’ homeland. The historic downtown village features a mixture of Georgian, Federal, and Greek Revival architecture, with well-preserved red brick buildings lining the main drag and a historic town square called the Green.

Stroll through the square and stop by the town’s 139-year-old general store, F.H. Gillingham and Sons, before exploring Vermont’s rural beauty via car. A scenic drive through the area features rolling farmland, covered bridges, historic barns, and easy access to nature at the nearby Mount Tom and Quechee Gorge.

Lititz, Pennsylvania

Stepping into Lititz feels like stepping back in time. The town was founded in 1756 by a religious community that barred entry from outsiders for nearly a century. By the turn of the 20th century, however, Lititz opened its doors to the public, and evolved into a more welcoming community. 

Whether you’re looking for a place to stay the night or just a cold pint, Lititz Springs Inn will do the trick. Built in 1871, the historic inn was once frequented by gold rush pioneer John Sutter, who lived across the street. (Rumor has it, his ghost still likes to visit.) History buffs can explore the town’s other historic buildings on a walking tour, while foodies should check out America’s oldest pretzel bakery, the Julius Sturgis Pretzel Bakery, or visit in October for the annual Lititz Chocolate Walk.

Stonington, Maine

Located on Maine’s midcoast, this working fishing village has a ruggedly charming feel — with lobster boats, rocky coastlines, and a bustling harbor. As an unofficial artist haven, Stonington is also home to art galleries, craft studios, and small cafes in the well-appointed downtown, which lacks the rampant commercialization you might find in other popular towns up and down the coast. 

After admiring the pretty clapboard homes and cedar-shingled buildings, check out the nearby Crockett Cove Woods, which are frequently draped in a mystical fog, or hop on the mailboat for a tour of East Penobscot Bay and a trip to Isle au Haut, which contains a section of Acadia National Park.

Cold Spring, New York

Located along the Hudson River, Cold Spring is not only one of the prettiest towns in the Northeast, but also an easy day trip from New York City. Start the day by exploring the Cold Spring Historic District, which includes Main Street and well-preserved 19th-century homes, churches, and storefronts.

Next, check out the Cornish Estate Trail, a 1.8-mile hike that leads to ruins of a magnificent old estate from 1910. (If you’re feeling extra motivated, you can extend the hike to a 5-mile loop.) End the day with a trip to Manitoga, a midcentury architectural masterpiece that was inspired by Frank Lloyd Wright and is tucked into a peaceful 75-acre preserve, before hopping on the train back to the city.