Skip to Content

Click on a label to read posts from that part of the world.

Map of the world

New Canaan, Connecticut: What can you do in the town with the wealthiest residents?

Whenever there's a list of cities or neighborhoods like the ones that are dying or thriving the most, I flip through them looking for a connection.

I was surprised to find one on the list of Top-Earning Towns. It's not where I generally hang out--trust me, I couldn't even afford to live in a garage there, but I've been to New Canaan, Connecticut several times. It's the town near to where relatives of mine used to live until last year when they headed for new digs in North Carolina.

When I think of New Canaan, and the area around it, I don't think of big houses, but of a place where country roads still wind through woods of enormous trees edged by stone walls.

Sure there are big houses, but the area has retained the beauty of the natural environment. New Canaan, described on a realty company's Web site as evoking images of a Norman Rockwell painting, is a place where people's clothes are pressed. There is even a park called Bliss Park where the New Canaan Nature Center is located.

Besides visiting the town, this is a region of the U.S. to see fall foliage, and take in fruit and vegetable stands and antique stores along the way. This is also the land of small white churches with graveyards of weathered tombstones on gentle slopes of hillsides. Picturesque with a capital P.

This part of the United States is not one that crackles with excitement, but because it's close to Manhattan there are a lot of famous folks who have called New Canaan and other close by towns home--David Letterman and Katherine Heigl, for example. Although, Letterman may have moved, and Heigl left here for California.

One place that my relatives always took me whenever I visited is Cannondale Crossing in Wilton, the town that is virtually next door to New Canaan.

Also referred to as Cannon Crossing, this cluster of buildings looks a bit like a village, although this is the type of village where no one lives. Instead, the assortment of historic houses and buildings were moved here long after they served their use in their original location. Here they were restored and turned into shops and galleries.

The red school house, however, now a restaurant, is original to the location. Cannondale Crossing is the kind of place you can find good deals on unusual, more upscale holiday items after the holidays. That's what I've bought. I have a hard time passing up bargains.

When I first visited my relatives, I was told the story of how the Cannondale Crossing was created by the actress June Havoc, who is the same June as the girl in the musical "Gypsy." "Gypsy" is based on June Havoc and her mother's life back when June was a child performing in vaudeville. She later grew up to be a successful actress and director.

Finding out that "Gypsy" was based on a true story and that June grew up to create her own faux village impressed me as much as the houses where the affluent folks live.

Filed under: Arts and Culture, Business, Food and Drink, Stories

Search Travel Deals

Add your comments

Please keep your comments relevant to this blog entry. Email addresses are never displayed, but they are required to confirm your comments.

When you enter your name and email address, you'll be sent a link to confirm your comment, and a password. To leave another comment, just use that password.

To create a live link, simply type the URL (including http://) or email address and we will make it a live link for you. You can put up to 3 URLs in your comments. Line breaks and paragraphs are automatically converted — no need to use <p> or <br /> tags.

Gadling Features

Categories

Become our Fan on Facebook!

Featured Galleries (view all)

The Volvo Ocean Race onboard Team Abu Dhabi
Virgin Galactic's Gateway to Space
Breakfasts around the world
FoodFlags
Outrageous State Fair Foods
The world's ten most uninhabited countries
Yellowstone in pictures: 2011
Most crowded islands on earth
Burj Khalifa: The tallest building on the planet

Our Writers

Grant Martin

Editor-in-chief

RSS Feed

Don George

Features Editor

RSS Feed

View more Writers