By John Engel
Fourteen years ago, I wrote “Top 10 Reasons New Canaan is Unique” in the New Canaan Advertiser. The article was reprinted in the Patch, where you can still find it. It’s time to update that list and note what has changed.
1. Schools
In 2012, we had the top school system in Connecticut, and we still do. According to Niche, we’re currently #2, behind Westport, ahead of Darien and Wilton. USNews ranks South School #3 in the state, behind schools in Greenwich and Fairfield, but SchoolDigger still has New Canaan as #1, two years in a row.
Schools are the top reason young families move to New Canaan, and the knock-on effect is that seniors often move here to be near their grandchildren. No other district has this consistent pattern of excellence district-wide over the span of several decades.
2. Taxes
We had, and have, the third-lowest tax rate in Connecticut (ignoring Washington and Salisbury). New Canaan (16.61) is still behind Greenwich (12.04) and Darien (15.48), but over the past eight years (2018-2025), the average increase in the total amount raised by taxation has been only 2.3% per year. New Canaan has exhibited extraordinary fiscal discipline while investing in major infrastructure projects during a decade where inflation averaged 3.05%.
3. Village
The charm of a walkable village sets New Canaan apart from her rivals and remains a major asset, defended fiercely. In a dozen years, we’ve renovated the Playhouse, town hall, and fire and police stations, and preserved our historic library. We’re not stuck in the past: St. Aloysius school, the Millport apartments, Canaan Parish, Burtis Avenue, and The Vue are examples of major projects in a downtown soon to get its first hotel.
4. Restaurants
New Canaan has become the de-facto destination for food in Fairfield County, with over 30 first-class restaurants packed into the walkable downtown, each spilling out onto the expanded sidewalks during warm weather.
The effect has been profound. Watch as drivers, walkers, and shoppers connect with diners as they thread their way past the tables, calling out greetings, waving hello, and just generally connecting. It’s really quite remarkable and unique in a town of this size in 2026.
5. Clubs
While town life doesn’t revolve around membership to a club, there are over a hundred clubs here, bringing people together and serving every possible interest, including the Winter Club, the Field Club, the Racquet Club, the Rotary Club and the Garden Club, to name a few. The newly renovated New Canaan Country Club is limited to New Canaan residents, a fact that makes it uniquely locally oriented in Fairfield County. The YMCA, New Canaan Library, Lapham Center, and Men’s Club are very active, hosting many specialty clubs.
6. Waveny Park
Unchanging, and yet so changed these dozen years. The town pool was new. We added new paddle courts, and baseball and softball fields. We expanded and renovated the Carriage Barn, Powerhouse Theater, and playground. We added the Boucher Rink and, at the mansion, we fixed the roof and installed new ramps, bathrooms, and an elevator.
The Family Fourth is still the biggest party, but Caffeine & Carburetors is now a fixture in Waveny twice a year, and nearly as large. This 130-acre park gets a quarter-million visitors per year — not hard to imagine if you’ve seen 800 children playing soccer there on a Saturday morning in season.
7. Recreation
A dozen years ago, Irwin Park’s rubber jogging paths were relatively new, and Mead Park was freshly dredged for the first time in decades. Once COVID hit, the world took a greater interest in parks and open space, for a while there, elbowing our neighbors out of the way as we took to hiking the trails with a vengeance.
The New Canaan Land Trust created the Green Link connecting Irwin Park to the Nature Center, acquired the Silvermine-Fowler preserve, and restored dozens of new trails on 60 properties they own around town. Grace Farms opened in 2015 and has been a major draw (worldwide) for its architecture, its programming, and recreation of all sorts.
Organized recreation? Probably too many to name: Parks & Rec runs the town pool, tennis, pickleball, and dog parks. Add the renovated YMCA, New Canaan Chamber Music, Carriage Barn and Silvermine Arts, the Powerhouse, Summer Theater, Academy of Dance, Racquet Club, youth football and lacrosse under the lights at Dunning, paddle at Waveny, platform tennis tournaments in January snow, and adult leagues that fill before the email confirmation hits your inbox. It isn’t one field, court, or stage. Recreation here is layered: passive and organized, competitive and contemplative.
8. Community Spirit
I wrote, “From Christmas Caroling on God’s Acre to our Memorial Day Parade down Main Street, to the Ice Cream Social at the Historical Society and our spectacular 4th of July celebration complete with fireworks at Waveny Park, we above all share the guiding belief that all are welcome. While young families move in, our baby boomers and seniors seem to be staying on, making our community rich in its diversity.”
That was true in 2012. All of that is still true, and we’ve added or improved so many more community events since. Ballet on the Library Green, Restaurant Week, Caffeine & Carburators, Christmas Stroll, Menorah lighting, the Halloween parade, and Veterans Day on God’s Acre are just some of the fixtures of community life. The New Canaan Community Foundation helps anchor that effort, supporting the nonprofits and volunteers who quietly do the work between the events. Community spirit here isn’t just tradition. It’s participation — structured, supported, and passed from one generation to the next.
9. 44 Miles to New York City
This is one thing that has not changed, although how we think about commuting has. Cars are faster and safer, and the Merritt Parkway that we rely on is more beautiful, having been repaved and thousands of hazardous trees cleared away. The biggest change since 2012 is our ability to work from home, or the park, in a wireless world, making our dependence on New York City just a bit different.
10. Next Station to Heaven
I’m speaking about New Canaan’s train station, where train routes have started and ended since 1868, ensuring New Canaanites always get a seat. If you’ve missed the New Canaan train and had to board in Darien, you know the difference. It’s truly a unique arrangement that we have here.
Fourteen years ago, these 10 distinctions were advantages. Today, they are moats.
Schools that stayed excellent. Taxes that stayed disciplined. A village that modernized without losing scale. Parks expanded. Restaurants improved. Community rituals multiplied. Even commuting evolved without diminishing proximity.
Most towns change. Few towns change without losing themselves. What strikes me isn’t what’s different; it’s what has held.
New Canaan hasn’t chased trends. It has layered strength on top of strength. And that, more than any individual item on this list, may be what truly makes it unique.
John Engel is a broker on the Engel Team at Douglas Elliman, and his earliest memories of New Canaan are of getting lost in the woods behind St. Luke’s School, circa 1973. Change is hard. Every improvement listed above followed real community debate and compromise. That process can be uncomfortable, but it is also the reason the town evolves without losing itself. When residents participate, the results tend to endure.
