Connecticut and the Berkshires – The New England Road Trip You Didn’t Know You Needed

From historic seaports and culinary experiences to covered bridges, chocolate farms and Norman Rockwell masterpieces, Connecticut and the Berkshires reveal a quieter, more authentic side of New England.

New England is often synonymous with colourful autumn leaves, lobster rolls and quaint villages, but Connecticut and neighbouring Berkshire County in Massachusetts deserve far more than a fleeting stopover. Linking charming maritime towns with rolling countryside, historic farms, celebrated art museums and unforgettable culinary experiences, this region is made for travellers who prefer to slow down and savour the journey.

Travelling by car is undoubtedly the best way to discover this corner of the United States. Every winding country road reveals another postcard-worthy village, while rivers, forests and covered bridges create scenery that feels lifted straight from a Hollywood movie.

Discover Mystic, Connecticut’s Historic Maritime Heart

Our journey began in Mystic, arguably Connecticut’s most famous coastal town. Sitting on the banks of the Mystic River, this historic port perfectly blends New England charm with a thriving food scene.

Lunch at S&P Oyster Club overlooks the river, where boats drift lazily beneath Mystic’s iconic 102-year-old drawbridge as it regularly rises to allow taller vessels to pass. Naturally, seafood takes centre stage here.

Connecticut is famous for its hot buttered lobster roll – unlike the cold, mayonnaise-based version found elsewhere in New England – and it’s every bit as indulgent as it sounds. Littleneck clams, fresh lobster ravioli and locally harvested oysters are equally irresistible.

After lunch, we wander through Mystic’s boutique-lined streets. Stores selling artisan kitchenware, gourmet teas and handcrafted gifts make browsing a pleasure, while bakeries such as Sift tempt visitors with divine freshly baked pastries. Fans of the 1988 film Mystic Pizza can also stop by a pizzeria of the same name. It isn’t ‘the’ pizzeria though.

Step Back in Time at Mystic Seaport Museum

No visit to Mystic is complete without spending several hours at the remarkable Mystic Seaport Museum.

More than simply a museum, it’s a recreated 19th-century seafaring village built using authentic historic buildings relocated from around New England. Blacksmiths, coopers, shipwrights and printers continue practising traditional trades, preserving skills that have almost disappeared elsewhere.

The highlight is boarding the Charles W. Morgan, built in 1841 and the last surviving wooden whaleship in the world. Walking its decks offers a sobering glimpse into the lives of sailors who sometimes spent more than a decade at sea.

With more than 500 historic vessels, fascinating exhibitions and a waterfront tavern serving classic New England clam chowder, it’s easy to spend an entire day here.

A Culinary Escape at Hunt Hill Farm

 

Leaving the coast behind, we head inland through Connecticut’s picturesque countryside to Hunt Hill Farm near New Milford.

 

Dating back to 1760, the beautifully preserved property is steeped in fascinating history. Established by legendary conductor Skitch Henderson and his wife Ruth, the farm became a retreat for celebrities including Frank Sinatra, Diana Ross, Keith Richards, Andy Warhol and Liza Minnelli.

Today it’s also home to the renowned Silo Cooking School.

Joining one of the hands-on cooking classes is one of Connecticut’s hidden gems. Working alongside experienced chefs, guests prepare seasonal dishes inspired by both Southern American and Mediterranean traditions before sitting down to enjoy the meal together. It is quite something to be cooking in the very place where Julia Child, Martha Stewart and Jacques Pepin started the trend of filming while cooking.

For those wanting to immerse themselves even further, overnight cottages allow visitors to linger a little longer in this remarkable setting. If you’re lucky, you could stay in one with one of Skitch Henderson’s famous Steinway grand pianos.

Road Tripping Through Connecticut’s Litchfield Hills

One of the greatest pleasures of exploring Connecticut is simply driving.

The Litchfield Hills are a landscape of dense forests, rivers, stone walls and winding country roads connecting impossibly pretty towns such as Washington, Kent, Cornwall and Goshen.

Fans of Gilmore Girls will immediately recognise many of these locations, as the series drew inspiration from the region’s picturesque villages.

Historic covered bridges appear regularly throughout the drive, each originally built to protect timber from harsh New England winters. Crossing the Cornwall Covered Bridge feels like travelling back in time.

Every town offers another reason to stop – whether browsing independent bookshops, local cafés or quirky hardware stores where even an ordinary fly swat somehow becomes the perfect holiday souvenir. I know, it is weird but it is a fact – Helen did buy a fly swat.

Fresh Chocolate Straight from the Farm

One of the journey’s sweetest discoveries was Thorncrest Farm & Milk House Chocolates in Goshen.

This family-run dairy farm produces handcrafted chocolates using exceptionally fresh milk from its own Holstein cows. The farm prides itself on natural farming methods, while visitors can watch the cows pampered in the barn before sampling chocolates that are remarkably rich and creamy.

It’s the kind of authentic, small-scale experience that perfectly captures rural New England.

Coffee Stops, Scenic Walks and Hidden Discoveries

Every great road trip develops its own traditions, and ours quickly became the daily search for excellent coffee.

One memorable stop was Great Barrington, where we had probably the best coffee from our trip at Cafe Holli. Just opposite, stroll down a narrow laneway to the River Walk on the banks of the Housatonic River.

Along the way we encountered deer crossing country roads, traditional fairs, rodeos, stone fences built centuries ago and charming villages that seemed untouched by modern life.

Norman Rockwell’s America Lives On

Crossing briefly into western Massachusetts brought us to one of America’s finest art museums.

The Norman Rockwell Museum in Stockbridge celebrates one of the nation’s most beloved illustrators, whose paintings captured ordinary American life with extraordinary warmth and humanity.

Rockwell’s famous Four Freedoms paintings remain deeply moving, while works such as The Problem We All Live With reveal his willingness to tackle important social issues.

Many visitors find themselves unexpectedly emotional walking through the galleries. Each painting tells a story, inviting viewers to linger a little longer and discover another detail.

Outside, Stockbridge itself is every bit as charming as Rockwell painted it. During the Christmas season, the town famously recreates one of his best-known works, transforming Main Street into a living version of his iconic painting.

Where to Stay in Connecticut

For travellers exploring the Litchfield Hills, Heritage Hotel Golf, Spa & Conference Center in Southbury makes an ideal base.

Its spacious rooms overlook rolling fairways where Canada geese gather in the early morning mist, while facilities include a golf course, spa, swimming pools, fitness centre and restaurant. Most importantly, its central location makes day trips throughout western Connecticut wonderfully easy.

Why Connecticut Belongs on Every New England Itinerary

Connecticut often sits quietly in the shadow of its better-known New England neighbours, yet that may be precisely its greatest strength.

Its coastal towns remain wonderfully authentic, its countryside feels refreshingly untouched, and its culinary experiences celebrate local produce without pretension. Add world-class museums, fascinating history, charming villages and unforgettable road-trip scenery, and you’ll quickly discover that Connecticut and the Berkshires are far more than a stop between Boston and New York.

They’re a destination in their own right – and one that rewards travellers who take the scenic route.

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