Discovering New Canaan, CT – An Insider’s View

Nestled just 40 miles outside of the Big Apple, New Canaan, CT is about as picturesque as a town can get. Brick storefronts and restaurants line the downtown streets while residents meander about on sun-soaked afternoons – shopping, visiting, running and biking.

For a sleepy “little” village, entertainment options rival that of any city.

Take in a movie at the playhouse. Tour one-of-a-kind architectural attractions like The Glass House or Grace Farms. Sip wine with friends at one of the many bistros or simply enjoy the fresh air in the town’s numerous parks and open spaces.

Quick History of New Canaan, CT

Discovering New Canaan, CT - An Insider’s View

Incorporated in 1801, but settled in 1731, New Canaan found its start as one of the most notable shoe-making hubs in New England. In support of the industry, tanneries and bark mills set up shop near town center, and as early as 1818, New Canaan, CT was credited with making over 50,000 pairs of shoes.

Within a few decades, transportation evolved and the addition of the city’s iconic train station made the area accessible for New York City’s thought leaders. Large summer homes were built on the outskirts of town, overlooking the countryside, and eventually, many part-time residents settled into full-time status.

Breathing Life Into a Forgotten Greek Revival

Discovering New Canaan, CT - An Insider’s View

Well-manicured properties and stunning architecture are now visible at every turn, making New Canaan the perfect setting for the revitalization of a forgotten Greek Revival located within God’s Acre.

Enter This Old House Ventures, America’s leading home-enthusiast brand, widely known for its 40+ year television show This Old House.

In conjunction with Karp Associates, Inc. (a well-known New England construction firm based right in New Canaan) and numerous partners like Baird Brothers Fine Hardwoods, This Old House set the stage for its 5th Annual Idea House project, restoring the facade of an 1840’s Greek Revival while building a thoroughly modern home behind it.

The 2019 Idea House debuted in the Nov/Dec 2019 issue of This Old House Magazine and online at

Noteworthy Facts about the Fairfield County, CT Town

Discovering New Canaan, CT - An Insider’s View

With a population of less than 20,000, New Canaan is far from being a metropolis. It is, however, one of the richest towns in the nation, ranking 17th in CNN’s 2014 list of the top-earning zip codes. (A median income of $540,235 and median home price of $1,635,000 is pretty impressive!)

The New Canaan Public School system is nationally recognized, as well. In 2019, the district ranked sixth-best public high school in Connecticut, and in 2010, Forbes listed New Canaan as the third-ranked school district in the U.S. for communities with a median home price of $800,000 or more.

In the Media

Awareness of this quiet New England town goes beyond its educational excellence and prosperity, however.

If New Canaan is looking (or sounding) familiar to you, that’s probably because This Old House isn’t the first media brand to take interest in the nostalgic colonial feel of the popular Fairfield County town.

While This Old House’s 2019 Idea House is New Canaan’s most recent claim to fame, you’ve seen glimpses of the community in a variety of movies, including The Stepford Wives (2004) and Revolutionary Road (2009).

There’s also a laundry list of the rich and famous who (in some way shape or form) have called New Canaan home:

    • Katherine Heigl, actress
    • Christopher Lloyd, actor
    • Harry Connick, Jr., singer
    • Paul Simon, singer
    • Ann Curry, journalist
    • Brian Williams, journalist
    • Jeff Checketts, former CEO of Madison Square Garden

And, that’s just to name a few!

Interestingly, the town’s old-world charm isn’t the only style to define the community’s history of great architecture. Between 1940 and 1960, New Canaan paved the way for the modern architecture movement when a group of students and teachers from Harvard Graduate School of Design moved to town.

A few of those members in particular – known as the Harvard Five – contributed significantly to the movement, helping to design nearly 80 modern homes that featured open floor plans and new-age materials (one of those properties being The Glass House, mentioned above).

The Perfect Weekend Get-A-Way

Discovering New Canaan, CT - An Insider’s View

Looking for a unique weekend get-a-way? This town should DEFINITELY be on your shortlist!

Searching for a quiet town with New England-style charm? New Canaan. Planning a shopping trip inclusive of unique boutiques and high-end retail – only an hour away from New York City? New Canaan. Infatuated with intricate architecture and searching for a place that has it all? You guessed it – New Canaan!

For more on the town’s most recent claim to fame, the 2019 This Old House Idea House, check out our blog for details of the 6,000 square foot home or shop the look at Baird Brothers Fine Hardwoods!