New England is neither ‘new’ nor ‘English’. But it is one of the oldest clearly defined regions in the US. Stretching across six states, this northern nook of the country is famous for its rich history, beautiful landscapes, and distinct seasons. Whether for the fall foliage or the sunny summer beaches, there is always a reason to explore New England’s quaint towns and scenic drives.
As a foodie who loves spending time outdoors and learning about history, I can confidently say that New England is one of the most beautiful and inspiring places I’ve visited.
If a trip to New England is on the cards, do yourself a favor and consider visiting a few of these charming small towns:
11. Westerly, Rhode Island
Rhode Island’s southernmost town, Westerly, is one of the most beautiful little seaside towns that truly lives up to the state’s nickname, ‘The Ocean State’. It’s as if ‘long walks on the beach’ were invented along the three-mile-long Misquamicut Beach.
But apart from the stunning coastline, Westerly has a lively downtown with local shops and boutiques. This is where you will also find the historic Granite Theatre and relaxed Wilcox Park. And no visit to this town is complete without a taste of clam chowder at one of the seaside shacks. With food this good and views this beautiful, Westerly feels a bit like a well-kept secret.
10. Manchester, Vermont
Manchester, Vermont, is a tiny town of less than 5000 people. Being a local here feels like being a part of a big family. And what better place to live with an extended family than in the shadow of Mount Equinox?
Not only is the landscape a dream come true for outdoor enthusiasts, but it’s also world-famous for its foliage that blankets the mountains each fall. As a strange yet inviting addition to the outdoors, the town is home to a huge designer outlet mall. However, those who prefer history to retail therapy might enjoy visiting Hildene, the Lincoln family home, or the niche American Museum of Fly Fishing.
9. Chilmark, Massachusetts
You may not have heard of Chilmark, but I guarantee you’ve heard about Martha’s Vineyard. Well, Chilmark is a small New England town on the island of Marthas Vinyard, which is known for its exquisite coastlines and moody seas.
And while the island isn’t exactly top secret, Chilmark still offers a slightly rural and low-key vibe compared to the rest of the island. Its main attractions are the fishing village and fish market of Menemsha, where you can taste the best lobster rolls in the region.
With its rolling hills and stone cottages, it also hosts the Martha’s Vineyard Film Festival, which takes place every spring.
8. Bar Harbor, Maine
Bar Harbor is a small fishing village on Mount Desert Island along the Frenchman Bay of Maine. But don’t be fooled; there is nothing ‘desert-like’ about this island. In fact, Bar Harbor serves as the gateway to the Acadia National Park, home to the incredibly lush Cadillac Mountains.
Bar Harbor itself is a surprisingly energetic small town. Naturally, it’s a hub for all sorts of outdoor travelers, including hikers, bikers, and kayakers. Aside from the national park, the town is home to the gorgeous Shore Path, a lively downtown with boutiques and eateries, and world-class lobster rolls sold on every street corner.
7. Mystic, Connecticut
Remember the 1988 movie called Mystic Pizza? Well, while Julia Roberts might have made the town famous, Mystic, Connecticut, is much more than just a film set.
The movie does get some things spot on. It’s a charming place that could make anyone want to give up the 9-5 grind for easy living in a small town. The seaside town is steeped in maritime history. The best place to learn about its history is at the historic recreation of Seaport Village, which offers a glimpse into the town’s seafaring past.
6. Provincetown, Massachusetts
Provincetown sits at the northernmost tip of Cape Cod. And unlike a lot of New England towns, this one appeals to a more laid-back, creative, and particularly a big LGBTQI+ crowd. It’s actually North America’s oldest continuous art community. So, you can imagine the abundance of art galleries and exhibitions on show throughout the year.
P’town, as it is known by locals, was one of the final destinations of the Mayflower over 400 years ago. It’s also famous for the historic Gifford House, an inn visited by actors and presidents, including Al Pachino, Bette Davis, and Theodore Roosevelt.
5. Sugar Hill, New Hampshire
Taking a break from the seaside villages, Sugar Hill in New Hampshire gives these coastal towns a run for their money with sweeping hills covered with flowers. The town sits on a mountain overlooking the White Mountain National Forest, with sweeping views of the Presidential, Franconia, Kinsman, and Dalton Mountain ranges.
If you’re into gardening or just appreciate the wonder of flowers, this entire region gets carpeted in towering lupine flowers throughout summer. It’s so impressive that the town even hosts an annual Lupine Festival in June, during which the fields are painted with vibrant purples and pinks.
Flowers aside, Sugar Hill is also known for its pancakes, particularly those from Polly’s Pancakes – they’ve been perfecting their recipe since 1830.
4. Stowe, Vermont
Stowe might be one of the most popular towns on this list, partly because of its reputation as a ski resort during the winter months. But Stowe is up for adventure no matter the season. Sure, in winter, it’s a skier’s paradise, with a cozy mountain town perfect for a family-friendly adventure.
Come summer, the hiking and biking trails attract scores of visitors, from professionals to leisurely riders and hikers. Spring sees fireworks of wildflowers, while fall is famous for its yellow and orange foliage. The town is just as exciting, scattered with boutiques, galleries, and eateries – the perfect addition to a day in nature.
3. Ogunquit, Maine
The name Ogunquit directly translates to ‘beautiful town on the sea’ in the Abenaki native language – and it certainly lives up to its name. This small, picturesque town in Maine is best known for its artistic community and beautiful beaches.
Part of its allure is thanks to its 1.25-mile walking path called The Marginal Way, which winds its way along the ocean. But it’s just as easy to get lost in the art galleries and small shops as it is in the town’s stunning beaches. One of my favorite things about this town is the old trolley system, which makes it easy to get around without a car.
2. Oak Bluffs, Massachusetts
Oak Bluffs is another town on the iconic Martha Vineyard isle. It’s one of the most charming seaside towns on the planet, with an eclectic downtown with historic cottages and too many seafood restaurants to count.
With bougainvilleas lining the streets, sandy beaches, and Victorian cottages that look like gingerbread houses, this town looks like it fell straight off the pages of a fairy tale.
Oak Bluffs’ African American heritage is celebrated in style here, particularly at Inkwell Beach, a place that is as historically significant as it is beautiful.
1. Woodstock, Vermont
Imagine a town so picturesque it feels like stepping into a painting. This is Woodstock for you. Located in the heart of Vermont, this gorgeous town of classic farmsteads, covered bridges, and forested hills is the most charming in the region.
Many of its buildings have been standing since 1761, when the town played an important part in the colonial history of the U.S. Fall is easily the most beautiful time to visit, when the hills come alive with color before shedding their leaves for winter. Throw in some cozy cafes, maple syrup farms, and a few ski resorts, and it’s no wonder Woodstock tops this list of charming New England towns.
Leave a Reply