11 of the Most Beautiful Historic Towns in New England
The northeastern corner of the continental United States is New England, a region of six small yet beguiling states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. They are a bundle of travelers' favorite destinations, with breathtaking landscapes of the Atlantic Coast and the mountainous inland and a rich cultural heritage that can easily transport one back in time. Being one of the earliest areas of the "New World" that was settled by the English, history is at every turn, and many towns across the six states are a living museum of the colonial period, along with their unique flair and character that never fail to entice every visitor. Whether visitors like being close to the shore or tucked away in the hills, the historic towns of this region have a bit of everything to suit any taste!
Kennebunkport, Maine
First settled in 1653, Kennebunkport got its name from the nearby Kennebunk River. Back in the day, it was a fishing and shipping port for its ideal location on the river and the sea. The seaside town today is a popular summertime resort, which started in the 1870s when many holiday homes were built along the coast. While many visitors come here for the beaches, Kennebunkport is a delight for the explorers, with a historic district that continues to radiate the charm of a classic resort town. Begin at Dock Square, where most of the best restaurants (such as Alisson's) and retail shops are found. Travelers can find the White Columns Building nearby, a 19th-century Greek Revival mansion that has preserved its original rooms and furnishings of a local family while also having an exhibit of former President George H. W. Bush, who had a summer home at Walker's Point that is still being resided by his family today. The Ocean Avenue is a lovely drive that brings visitors to the historic St. Ann's Church, and splendid coastal views, the kind that have inspired many painters in the past couple of centuries. Admire some of their artworks at the Landmark Gallery before proceeding north, where one can photograph the iconic Wedding Cake House and visit the interactive and fun-filled Seashore Trolley Museum.
Bennington, Vermont
Bennington is often said to be where the state began, as it was the first town to be chartered in Vermont's territory in 1749. When entering from the highway, travelers are most likely to catch a glimpse of the 306-foot-tall Bennington Battle Monument, the tallest man-made structure in all of Vermont, commemorating the victory of the battle that was a turning point in the American Revolutionary War. Steeped in history, Bennington is home to the oldest church in the state - Old First Church, dating back to the year 1762, which also houses a cemetery where many historical luminaries including famous poet Robert Frost were buried. At the Bennington Museum, many antiques and artworks from the region are displayed, the most noteworthy being the world's most extensive public collection of 20th-century folk artist Anna Mary Robertson "Grandma" Moses. The covered bridges are also worth mentioning, with five of them in the local county, spanning across the winding Walloomsac River with their red paint coat. Bennington has primarily grown to be a cultural center in this part of Vermont, with art galleries, workshops, and even a live theatre to impress. At the same time, it still retains much of its classic New England identity that many love Vermont for.
Nantucket, Massachusetts
Off the coast of Cape Cod, the island of Nantucket is a popular summertime destination with endless stretches of sand, sea, and sun to offer. The town of the same name is the main entry point to the island, serviced by ferries from the mainland and nearby Martha's Vineyard, where wooden wharves extend out to the water and reach oncoming boats, and the town center unfolds right in front of everyone's sight. Nantucket bears a unique historical profile reflected on its weathered wooden houses and old-brick mansions, connected by a network of cobblestone streets not only for pedestrians to walk on. Many buildings in the historic district have been transformed with a modern purpose. The Whaling Museum, for example, is set in a former candle factory with a hovering whale skeleton and vintage maritime artifacts on display. Walk on Main Street to admire its outstanding preservation of an 18th- to 19th-century streetscape before branching out to the neighboring lanes where many local boutiques continue the age-old tradition of scrimshaw and lightship basket crafting. Other sites include the Old Mill, Quaker Meeting House, and the Brant Point Lighthouse at the far eastern end of a sandy spit.
Camden, Maine
Camden is well-positioned on the western side of Penobscot Bay, with hills and forests occupying its immediate surroundings. The town, which dates back to the 1760s, originally thrived from shipbuilding, anchor manufacturing, and lime producing; the latter was a shared industry with neighboring Goose River (now Rockport). Like many coastal towns in Maine, Camden began to attract many vacationers in the summer during the 19th century, who built estates and mansions that have mostly been turned into bed and breakfasts today. Although largely destroyed by a fire in 1892, the downtown area of Camden was reconstructed with solid brick and has been revitalized with antique stores, art galleries, and great coffee spots like the one at Owl & Turtle Bookshop. Catch a musical performance or a comedy show at the Camden Opera House, with a beautifully decorated interior of chandeliers and wall designs. If you do not get seasick easily, a boat tour from the harbor is an excellent way to see the town from the water and spot the hidden Curtis Island Lighthouse. It is hard to resist a lobster roll in coastal Maine, and the town's very own Peter Ott's on the Water is known to serve the best-tasting selections along with clam chowder and oysters to go with.
Mystic, Connecticut
One of Connecticut's loveliest corners, Mystic is a small town on the eastern side of the state, right where the river of the same name flows out into the Fishers Island Sound. Founded in 1654, Mystic has a shipbuilding past as well as being a shelter for tall ships when there were terrible storms. These pieces of history can be traced back at the Seaport Museum today, one of America's most significant maritime museums, where visitors can imagine themselves in a 19th-century seafaring village and stand under the sails of the Charles W. Morgan whaleship. Explore the historic downtown, come across centuries-old churches and establishments like The Whaler's Inn, cross the iconic Bascule Bridge over the river, and see local paintings and sculptures at the Mystic Museum of Art and Courtyard Gallery. Continue upriver to find the Olde Mistick Village, a destination where boutiques, cafes, and restaurants are confined in a recreated traditional New England village. When September arrives, the country's oldest steam-powered cider mill - B.F. Clyde's Cider Mill opens its doors to visitors to taste what is known as "The best sweet cider on Earth" and sells fruit jams, honey, and fudge throughout the fall season.
Grafton, Vermont
Grafton is a town that acts like a village, with a very small population of around 600 people, it sits in the mountains of southern Vermont. The town has been nicely restored by the Windham Foundation and the people who proudly call it home, where historic residences still stand and look fairly new, set in a beautiful foliage of green in one half of the year, and orange in a short quarter after. Learn about the area's history at the Grafton Historical Society Museum. At the same time, part of the African American Heritage Trail is the Turner Interpretive Center, telling the story of escaped slave Alec Turner and his family who made this place their "journey's end." Founded in 1892 is the Grafton Village Cheese Company, a place to understand the process of making dairy products back in the day and the chance to sample them. Vermont is famous for its maple syrup. At the Plummer's Sugar House, visitors can experience the production of the sweet liquid year-round and purchase one of the goodies. Grafton may be tiny, but it is quite a memorable place that will stick to your mind for a while, so why not shop for a gift to take home, too?
Portsmouth, New Hampshire
Strategically located on the I-95 and separated from Maine by the Piscataqua River, Portsmouth is a large town with a lot of history to go with. Its founding years date back to the 1600s, when it was established to build a seaport with the use of shipbuilding, fishing, and fur trading. No longer are those industries active, however, Portsmouth continues to operate its port, where tugboats are seen escorting large ships in and out of the river. The action is best observed in Prescott Park, which has beautiful gardens and a signature view of the Memorial Bridge. Browse the shops and seafood restaurants of Bow Street, including River House, that have seating that faces the waterfront. The historic area of Portsmouth is best explored on foot, where visitors can find themselves discovering local artifacts and getting a hands-on experience in craft-making at a workshop in the 10-acre outdoor museum of Strawbery Banke, touring the historic homes of Warner and Moffatt-Ladd, or simply walking around Market Square. Farther away in the west, the USS Albacore Museum is home to a large naval submarine. While to the easternmost edge of New Castle, the 18th-century Portsmouth Harbor Lighthouse stands next to a ruined fort. Being so close to Maine, a quick trip to nearby historical sites such as Fort McClary can be quickly done with a short car ride away.
Bristol, Rhode Island
Dominating an entire peninsula between the bays of Mount Hope and Narragansett, the coastal town of Bristol is a mere 12-mile drive from the state capital, Providence. Named after the English city, the town is known for its deep water port and its shipbuilding industry, which has been in place since the 17th century. That legacy is displayed at the Herreshoff Marine Museum, with a collection of 60 boats, including the largest of the America's Cup boats. Part of the National Register of Historic Places list, the downtown area is made of classic New England homes, occasionally seen to be decorated with flags of the colors red, white, and blue. There are noteworthy buildings, such as the storied house of Linden Place and the English-style manor of Blithewold Mansion, which has an award-winning set of gardens. If there is one thing the town can claim, it is to have the country's oldest Fourth of July Celebration. Dating back to 1785, it is a three-week-long event that transforms Bristol into "America's most patriotic town", with concerts, competitions, and a historic parade to welcome the nation's birthday.
Provincetown, Massachusetts
The curl of Cape Cod's northwestern end is home to Provincetown, a place that prides itself on having 400 years of history, welcoming people worldwide. The town was first settled in the 1600s by the Pilgrims onboard the Mayflower, having braved through the Atlantic Ocean for over two months. It was also when the governing document of the Mayflower Compact was signed both events are integral to the town's history. They are commemorated at the towering Pilgrim Monument and Bas Relief Park. Ptown, as it is often known, is the oldest continuous art colony in the United States, it first began when Charles W. Hawthorne established the Cape Cod School of Painting in 1899. Today, the town is brimming with art venues ranging from the Provincetown Art Association and Museum (PAAM) to over 40 local galleries that line Commercial Street. Facing the water, Provincetown is a delight for seafood lovers and a cuisine that will come as a surprise - Portuguese food, where visitors can find freshly made malasadas and pasteis de natas at traditional pastry shops such as the Portuguese Bakery. Along with Cape Cod, the town is a popular beach destination in the summer, when loud and big festivities, especially toward the LGBTQ+ community, as it is well-known, take place.
Woodstock, Vermont
If looking for a town that perfectly fits the image of Vermont: red brick buildings, colonial churches, and a rural surrounding of farmlands and forested mountains, then Woodstock checks all the boxes. Chartered in 1761, the town quickly became an attractive hub for some of the earliest entrepreneurs in the state, drawing craftsmen and artisans to set their ground here. Today, Woodstock inspires artists near and far for its picturesque location in the Ottauquechee River Valley, where creativity is encouraged in places like the Artistree Community Arts Center and numerous small galleries and workshops. Known as "The Green", the downtown core of Woodstock comprises restaurants and coffee shops, including the local favorite Mon Vert Cafe and the informative History Center. Cross the Elm Street Bridge to visit the Billings Farm & Museum to learn about one of Vermont's most important agricultural heritage. The area is also home to the state's first national park - Marsh-Billings-Rockefeller National Historic Park, featuring a Victorian-style mansion and miles of trails to explore in a 550-acre protected forest.
Littleton, New Hampshire
"Be Glad" is the motto of this mountain town in the north of New Hampshire, derived from the famous children's storybook Pollyanna, written by Eleanor H. Porter, who called this place her hometown in 1868. Littleton honors the novelist with a bronze statue of the fictional character, which joyously welcomes every visitor with open arms. She stands in the center of Main Street, where most of the town's dining and shopping establishments are found. The Littleton Historical Museum is a short walk away from all the action, showcasing memorabilia and antiques collected across the region. The gushing flow of the Ammonoosuc River is a gentle reminder to relax and take in the beautiful natural surroundings, experience it by walking across the 300-feet long covered bridge, built next to the spinning mill of Schilling Brewery.
New England is a place to experience the foundation of America's modern history, the colonial and industrial past heritage, and the simplest pleasures of rural life. Traverse the mountains of Maine and the coastlines of Rhode Island; it does not take long to find the perfect town that matches these categories. No matter which visitors choose, they are quite the affirmation for a real-life history lesson!
