A New England road trip with historic river towns and incredible art trails

Upstate New York and the Massachusetts Berkshires both offer unique charms– one an iconic destination, the other more of a rising star off the beaten path. Together, they make the perfect long-weekend escape from the city.  

Art, nature, and good food define my ideal trip, and this road trip through Upstate New York and the Massachusetts Berkshires delivered all three in abundance. Just a few hours from New York City (or Boston!), the itinerary traces an easy arc from sculpture parks and historic river towns to one of the country’s most ambitious contemporary art museums. This forested region—home to a long-standing creative community, rural farmland, and winding, sun-dappled roads—makes for an ideal big-city escape for Australians visiting the American Northeast. 

Day 1: Art-filled stops in the Hudson Valley 

Walk the grounds to take in large-scale sculptures at Storm King Art Centre. (Image: Mary Cate McMillon)

If you’re driving upstate from New York City, the first thing you’ll want to put on your itinerary is to stop at Storm King Art Centre. Set across 202 hectares of rolling, wooded hills, this outdoor museum gives large-scale sculptures an entirely new context. In the fall, when I visited, the fiery fall leaves contended for the art’s spotlight. With so much ground to cover, you can rent bicycles to cruise between installations, though a leisurely walk is just as rewarding. 

Dine on farm-fresh produce at Blooming Hill Farm. (Image: Jessie Casey)

For brunch or lunch, head to Blooming Hill Farm to experience the region’s farm-to-table ethos right at the source; you’ll literally pass the fields where your meal was grown. For an even more immersive detour, drive a bit farther north to Fishkill Farms, where you can pick your own apples, berries, or stone fruits depending on the season. 

The riverside retreats at Hutton Brickyards. (Image: Hutton Brickyards/ Supplied)

Continue about an hour north to Kingston, New York, the state’s first capital city, established in 1777. You could stay among the historic downtown streets at Hotel Kinsley, but I opted for the riverside solitude of Hutton Brickyards. A former brick manufacturing site turned retreat, it offers standalone lakeside cabins that feel like a very grown-up, very luxe version of summer camp—minus the chaos and rigid schedules. Guests can book activities such as archery, morning yoga, or a session in the waterfront barrel sauna. 

Sonder brings out the best flavours from local ingredients. (Image: Mary Cate McMillon)

For dinner, look for the unassuming storefront that houses Sonder. Although presenting very much in its fresh, fun, natural wine bar persona, the menu goes far beyond typical wine-bar fare. Think: a whole chicken (feet included) bathing in jus, caramelised squash, and a delightfully excessive number of roasted garlic cloves—my idea of heaven. The wine list is just as playful, with cheeky descriptions (“getting a really buff partner to carry you through Comic Con dressed as a pirate and a parrot—you’re the parrot,” was a standout). It showcases how Sonder’s point of view is free of wine-world fussiness and focuses instead on the important things: seasonal products, buying local as much as possible, and a dedication towards reducing waste in the food industry.  

Day 2: From Hudson Valley History to Berkshires Art 

Begin or end your days by the river as the sun sets. (Image: Hutton Brickyards/ Supplied)

Your day begins lazily with the sunrise and mist over the Hudson and a walk on the Empire State Trail that cuts straight through the property. For breakfast, head downtown to Village Coffee and Goods for fresh-baked bread and pastries or Fantzye Bagels for a hand-shaped, sourdough bagel.  

Rough Draft Bar and Books has fantastic coffee and vibes. (Image: Supplied)

While you’re exploring downtown Kingston, don’t miss grabbing a coffee at Rough Draft Bar & Books. It sits at a fascinating intersection where all four corners feature buildings that have been continuously occupied since before the American Revolution. 

When you’ve had your fill of wandering Kingston’s cobblestone, old-Americana streets, hop in the car and cross into Massachusetts. The two-hour drive to North Adams is gorgeous—one of those stretches that reminds you it’s not just about the destination but the journey itself. Some of my favourite moments of the trip happened behind the wheel. 

MASS MoCA emphasises bold creative exploration in its exhibits. (Image: Mary Cate McMillon)

MASS MoCA is one of the most distinctive contemporary art museums in the country. The building began life as an industrial complex—first a textile mill, then an electrical plant producing components for World War II and NASA’s Apollo program. After the site sat vacant for years, Thomas Krens, then director of the Williams College Museum of Art (and later the Guggenheim), transformed it into a sprawling centre for contemporary art with more than 250,000 square feet of exhibition space. Despite the sheer scale and the number of large installations from both established and emerging artists, the halls and skybridges still feel remarkably open and expansive. 

Next door, Mexican-fusion spot Casita is the perfect place to grab a bite for dinner. One glance at the menu—featuring dishes like pistachio mole and street corn gnocchi—and I was sold. Afterwards, make the drive to Lenox for your overnight stay. 

Cornell Inn is just as magical in the winter. (Image: Cornell Inn/ Supplied)

The Cornell Inn exhibits all the best of a bed-and-breakfast. Housed in a stately Victorian home and carriage house, each guest room has its own design and personality. Little touches—like nightly cognac tastings and brownies at the front desk—prove how hospitality lives in the details. In a world where so many stays feel overly produced, this one is warm, intimate, and charming—perfectly in step with the Berkshires itself.  

The interiors of Cornell Inn exude charm and character.

Day 3: A day of art, authors, and nature in Lenox 

Norman Rockwell Museum houses a collection that honours the iconic American artist. (Image: Mary Cate McMillon)

After breakfast, I headed straight to the Norman Rockwell Museum. The artist, renowned for his illustrations of everyday American life in the 20th century, lived and worked for a significant period in Stockbridge, Massachusetts. His small studio was transferred to the grounds of the museum, and you can take a tour of the premises and pick up fascinating tidbits about his artistic process and inspirations.  

To continue the cultural thread in the area, you can explore the homes-turned-museums of two American literary giants: Herman Melville’s Arrowhead and Edith Wharton’s The Mount. 

High Lawn Farm’s ice cream is unmissable. (Image: Isabelle Crawford)

I also couldn’t help stopping by High Lawn Farm for their ultra-creamy ice cream and some cheese to save for happy hour. In summer, the Boston Symphony Orchestra takes up residence in Lenox at Tanglewood, giving classical music lovers endless opportunities to picnic on the lawns, sip crisp chardonnay, and enjoy world-class performances among the trees. 

The opportunities to enjoy nature are equally boundless. I went on a quick walk through Parsons Marsh Reserve for a dose of fresh air—just down the road from the iconic Stonover Farm, a fabulous six-room luxury inn. 

Wherever you wander during the day, end it with dinner at Cello. This intimate dining experience embodies everything that is so special about this corner of the Berkshires. Married couple Kim and Ryan Boya opened the restaurant about a year ago, and their personal touch is felt at every turn—Kim warmly chatting with guests in the dining room, and Chef Ryan bringing careful attention to detail in the kitchen. From the guest-beloved cornbread with maple butter (legend says some diners have eaten the butter with a spoon) to the celeriac prepared three ways alongside crisp-skinned trout, every dish feels thoughtful and deeply cared for. The wine list also surprises, with options from Massachusetts’ first natural winery and old-vine bottles from Mendocino. 

Make time to marvel at a sunset over the Hudson River. (Image: Hutton Brickyards/ Supplied)

This road trip loop through Upstate New York and the Massachusetts Berkshires balances culture, nature, and great, seasonal food without ever feeling rushed. It’s an easy breather from New York City or Boston—close enough for a long weekend, yet worlds away in atmosphere. And for Australians flying into the U.S., its straightforward access, forested landscapes, and standout art experiences make it an ideal introduction to the American Northeast.