Exploring New Canaan: Mid-century modern design, bountiful boutiques and top-shelf restaurants

Connecticut is famous for many things. Lobster rolls with melted butter. Holiday movies. The fierce divide between Red Sox and Yankees fans. But when bragging about our dear state, it never occurred to me to talk about mid-century modern architecture, a sleek aesthetic better known for places like Palm Springs.

Enter: New Canaan. Just 45 miles from Manhattan, complete with a direct train from Grand Central, it’s a town that’s seduced generations of New Yorkers who utter the words, “I need to get out of the city.” In the 1940s, it was also home base for the Harvard Five, who I like to imagine as a sort of architectural boy band. Thanks to their influence, New Canaan now boasts nearly 100 examples of mid-century modern design, and is an important stop on the modernism trail. 

As you might expect, the whole town is quite beautiful, including its fair share of grand Colonial-style homes and horseshoe driveways. But there’s a lot more to do than just ogle real estate. New Canaan has a thriving and walkable downtown, great shopping, scores of restaurants and some truly special public spaces. 

See + Do

When I hear about Grace Farms, my first question is, “What grows there?” The most accurate answer, if you’ll forgive the sentimentality, turns out to be peace. The land was formerly an actual farm, but today it’s a free (free!) place for the public to gather, appreciate nature and slow down. It’s also a marvel of modern design.

I follow the undulating, indoor-outdoor River building up the hillside, pausing in five communal spaces along the way. There’s the Commons, with long tables, a farm-to-table café and panoramic views. There’s the Pavilion, which hosts daily tea. There’s even a sports arena, ready for a game of pick-up badminton. An eclectic mix of students, baby strollers and seniors dot the walking paths. Grace Farms hosts a full calendar of community programming, if you want a structured activity. Or you can borrow my plan for my next visit: Toss a journal and a good book in a bag and call it an artist retreat.

Next, the anchor activity of my day: The Glass House. The signature work of the Harvard Five’s Philip Johnson, it’s one of New Canaan’s most iconic examples of mid-century design. Our tour group sets off in a posh van from the visitor center, which also happens to be The Glass House Design Store. As we make our way onto the Glass House grounds, I pretend I’m on the bus with the Velvet Underground, whose raucous party here in 1967 was shut down by the police, and Martha Stewart, who still attends an annual summer soiree and, I like to think, causes a ruckus of her own. Upon arrival, the house — which is truly glass on all sides — is a full-on forest-bathing experience, and a love note to clean lines and natural materials. I’ll never look at curtains the same way.

Take note: If art and architecture are your thing, New Canaan has a lot to choose from. The New Canaan Museum & Historical Society is an excellent place to start, with a walking trail that connects eight historic buildings and museums. That includes mid-century gem Gores Pavilion, located in Irwin Park.

For something a little less subtle, explore the Tudor-style “castle” presiding over the 300-acre Waveny Park, and be sure to visit the gallery space next door at The Carriage Barn Arts Center. Downtown, you can visit Heather Gaudio Fine Art (heathergaudiofineart.com) and Arden + White Gallery. On the eastern edge of town, Silvermine Arts Center (silvermineart.org) features a sculpture garden.

Eat + Drink

In my informal polling of locals for where to grab lunch, I hear one answer more than any other: Rosie. Food is the way to a town’s heart, and this place proves it. Twenty years ago, owner Rose “Rosie” Bonura was working as a private chef in New York, and reeling from a breast cancer diagnosis. She made a deal with God: If she survived, she’d open up her own place. She held up her end of the bargain with her namesake breakfast, lunch and brunch destination.

Located in the heart of downtown, Rosie offers two of my favorite things in a casual eatery: cookies the size of pancakes, and booze. It also has delicious tacos, sandwiches and a killer Sunday brunch. The whole time I’m here, a steady stream of regulars comes and goes, all smiles. The flowers are plucked from Rosie’s garden. Rosie herself is the kind of person who blows you a kiss just for swinging by. “I believe in generosity,” she says. “I want people to feel loved.”

For dinner, I am saved from analysis paralysis by another local tip — this time, from a woman in The Glass House tour group, who insisted I check out Pesca Peruvian Bistro. “Get the pisco sour, and you’ll understand,” she said. I do, and she’s right. The signature Peruvian cocktail arrives fresh, frothy and zingy. Between the ceviche and the nautical décor, I can practically feel a sea breeze. I send my source a telepathic thank-you. Locals always know best.

That said, New Canaan has a ton of food options, and when I asked around for recommendations, locals’ first response was almost always, “You can’t go wrong.” For upscale dining downtown, there’s Chef Luis, Elm, and Italian spots like Cava Wine Bar & Wood Grille, Solé and Spiga. Farmer’s Table is a farm-fresh eatery with a cozy ambiance. Dolce Italian Café doubles as a beloved coffee spot. 

For comfort food, pull up a booth at New Canaan Diner or Cherry Street East, or a stool at the long bar at Gates Restaurant + Bar. 

If you’re craving a slice, you’re in luck; New Canaan is blessed with quality pizza places. Joe’s Pizza and its New York-style pies have been part of the community since 1967, Locali serves traditional and high-end Neapolitan pies, and Dante’s Pizza fires up a Neapolitan-New Haven hybrid. For sandwiches, try long-time establishment Club Sandwich and newcomer New Canaan Butcher Shop. 

For your homegrown coffee fix, you can’t beat Connecticut Muffin or Zumbach’s Gourmet Coffee.

Shop

Here’s my advice to anyone planning a shopping day in New Canaan: Don’t forget to hydrate.

There are too many boutiques and shops for a full list, so instead, I’ll suggest a strategy. Step one: Park near Elm Street, somewhere between Main and Park. This puts you squarely in the walkable downtown. Step two: Pick one end of Elm to start. Step three: Work your way down and across the side streets till you reach the other end, or fall over trying.

As just a small sampling, this will include Found, The Whitney Shop, and Consider the Cook for home goods and gifts. It will bring you to Togs and She la la for boutique women’s clothing. You’ll discover antiques and vintage wares at Adirondack Store & Gallery and Odesmith & Richards. Luggage at Taylors Luggage. And jewelry and fine watches at Pennyweights, Wave and Manfredi Jewels. You’ll also find select retail chains.

Still standing? I hope so. You’ll want to save time and energy for Elm Street Books. Show me a community bookstore the likes of this one, and I will show you a vibrant town. It is big enough to have full sections of, say, poetry and design, and yet small enough to achieve that ideal of all bookstores: cozy. Plus, the staff is a marvel. In one brief visit, I overhear them recommend the perfect book for a 9-year-old boy (Hatchet by Gary Paulsen), have a spirited discussion about an obscure novel a customer happens to mention, and then, as their grand finale, give me the perfect pick for my next read (My Last Innocent Year by Daisy Alpert Florin), based on the campus novel I just finished. All this without blinking or, heaven forbid, turning to Google. It’s like a magic trick.

And that’s what we’re all looking for when we explore a new town, isn’t it? A little bit of magic. Some surprises and delights. A different perspective.

Quick facts about New Canaan

Founded: Established as a religious entity called Canaan Parish in 1731 from Norwalk and Stamford, New Canaan was incorporated in 1801.

County: Fairfield

Population: 20,622 (2020 Census)

Total area: 22.5 square miles

New Canaan Locals of Note

Christopher Lloyd (Back to the Future) was born in Stamford, but spent much of his childhood in New Canaan’s historic Waveny House, the jewel of a town park that his mother conveyed to the town in 1967. Allison Williams (TV’s Girls, the film Get Out) was born and raised in town, and fellow actor Katherine Heigl (TV’s Grey’s Anatomy; Knocked Up) was raised here.

Also born in Stamford but raised in New Canaan is the Washington Capitals’ goal-scoring Max Pacioretty. Sports talk personality Chris “Mad Dog” Russo has long lived in town.

NBC and MSNBC anchor Brian Williams lives in New Canaan, as did 60 Minutes’ Mike Wallace until his death in 2012 at age 93. Conservative commentator and writer Ann Coulter was raised in New Canaan.

Arthur Szyk, the anti-Nazi cartoonist and book illustrator who emigrated from Poland during World War II, lived in town until his death in 1951 at the age of 57. 

Rich Barton, CEO of Zillow Group and founder of Expedia, was raised in New Canaan.

Crooner Harry Connick Jr. splits time between New Canaan and New Orleans. Musicians Paul Simon and Edie Brickell had a home in town for about two decades before selling their 32-acre estate in 2022.