An Insider’s Guide to New Canaan

The architect behind Wadia Associates guides travelers through the perfect trip to the charming design town of New Canaan, Connecticut

Architect Dinyar Wadia has his Mumbai roots to thank for his early interest in British Colonial design. Since 1969, Wadia has lived in New Canaan, Connecticut, where he founded his architecture firm 45 years ago. During his frequent visits to Palm Beach to manage his South County Road outpost, he resides in a Chilean Avenue apartment, but his passion is the lovingly restored 1760 home he shares with his wife in New Canaan. When he’s not designing traditionally inspired single-family homes, he enjoys tending his garden and grounds. According to Wadia, New Canaan’s quaint charm, distinct seasons, and proximity to New York City make it a desirable destination. “Ever since the Harvard Five began designing modern homes here in the mid-twentieth century, New Canaan has drawn those interested in architecture and design,” he says. “It’s the quintessential New England town.” 

HOW TO START THE DAY With breakfast at Connecticut Muffin or fresh-made bagels from UCBC Bagels

WHERE TO EAT The Elm Restaurant for seasonal American fare

LOCAL DISHES TO DREAM ABOUT The ham terrine and the Grand Marnier soufflé at the Roger Sherman Inn, which you need to order ahead of time

FOR SOME SELF-CARE A massage at Greenwich Spa

WHEN TO GO Early to late spring, when the buds on the trees and shrubs are about to burst open, and also in the fall, early or late, depending upon the moisture content, which promotes the color change in the leaves.

Photo by Michael Biondo

A SOLO ACTIVITY Architect Philip Johnson’s Glass House is a shrine people visit from all over.

BEST SEAT IN TOWN The deck at the Tavern at GrayBarns on the Silvermine River

UNWRITTEN RULE THE LOCALS LIVE BY Dressing up is for the birds.

A CULTURAL OUTING Take in a Broadway show at the Powerhouse Theater.

HOW TO SPEND A FREE MORNING Go on a walking trip around New Canaan, with a stop on Elm Street to enjoy coffee at one of the smaller cafés. Then take a walk along South Avenue to the trails at Waveny Park or spend a lazy morning on the rear porch of Waveny House, overlooking the 300-acre park. 

SIGNATURE DRINK An espresso martini at Spiga


A MUST-DO EXPERIENCE Attend Caffeine & Carburetors, a showcase of classic and antique cars in the town streets on Sunday mornings a few times a year.  

MUST-GET MEMENTO The Harvard Five in New Canaan, a book about the mid-century modern architects who were prolific in New Canaan. It’s always available at Elm Street Books.

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