About an hour from New York City by train, the town is considered part of Connecticut's Gold Coast.

The town is bounded on the south by Darien, to the west by Stamford, on the east by Wilton, on the southeast by Norwalk, and on the north by Lewisboro and Pound Ridge in Westchester County, New York.

[2] In 1731, Connecticut's colonial legislature established Canaan Parish as a religious entity in northwestern Norwalk and northeastern Stamford.

As New Canaan's shoe business gathered momentum early in the 19th century, instead of a central village, regional settlements of clustered houses, mill, and school developed into distinct district centers.

The remark was found untrue and Kirk, after enduring the comments of others, wrote about a "dream" of approaching the Pearly Gates in the company of his fellow editors.

"Philip Johnson, Marcel Breuer, Landis Gores, John M. Johansen and Eliot Noyes – known as the Harvard Five – began creating homes in a style that emerged as the complete antithesis of the traditional build.

Using new materials and open floor plans, best captured by Johnson's Glass House, these treasures are being squandered as buyers are knocking down these architectural icons and replacing them with cookie-cutter new builds.

[7] Some other New Canaan architects designing modern homes were Victor Christ-Janer, John Black Lee, Allan Gelbin, and Hugh Smallen.

The film (and Rick Moody's novel of the same name, upon which it is based) takes place in New Canaan; a mostly glass house situated on Laurel Road is prominently featured.

Proximity to New York City proved worthy of its own connection to the New Haven Railroad, making New Canaan the only town with such a branch line.

Many New Canaan residents commute to New York regularly, with travel time to Grand Central Terminal around 65 minutes.

New Canaan is also heavily served by the historic Merritt Parkway, as the third municipality one traverses when driving through Connecticut from New York City.

[8] New Canaan was one of five towns in Connecticut that backed former Governor John Kasich of Ohio over Donald J. Trump in the 2016 Republican presidential primary.

[23] Holiday Stroll: Hosted by The Chamber of Commerce, downtown New Canaan celebrates with Christmas carolers, the lighting of the trees along Elm Street, the arrival of Santa Claus, and extended store hours.

[28] Juneteenth "Hearts of Freedom" Community Celebration put on by Stand Together Against Racism (S.T.A.R) annually on June 19 on the lawn of the New Canaan Historical Society.

Features live music, local black-owned food trucks, kids activities and is free to attend.

[36] In 2008, the median SAT score (verbal, math and writing) for district students was 1804, the highest in Connecticut.

[37] In its November 2009 edition, Connecticut magazine rated New Canaan's school system first among 29 towns with a population of 15,000–25,000.

[38] That category included Darien, Wilton, Ridgefield, Avon, Simsbury, Farmington, Southbury, Guilford, and other high-performing districts.

The ranking was based on 2007–2009 CMTs, results from the 2007–2009 CAPTs, local SAT scores for 2006–2008, and the percentage of 2007 high school graduates who enrolled in college.

[39] Twenty-two students in the New Canaan High School class of 2009 were National Merit Commended Scholars.

In addition to the award, the high school also received a $10,000 prize donated by Follet Library Resources.