My day began at Grand Central Station in New York City.
I got on a Metro North train toward Stamford, Connecticut, which would stop in Greenwich in under an hour. The train was fairly empty, but I imagined the train from Greenwich to New York City at the same time of day would be full of people commuting into the city.
My peaceful train ride lasted a little less than an hour before I got off the train at the Greenwich station.
One of the first things I saw after getting off the train was the headquarters of AQR Capital Management, a hedge fund that has about $226 billion in assets under management. Greenwich is home to several hedge funds, earning it the nickname "hedge fund capital."
After stepping out of the train station, I soon passed a car dealership selling Rolls Royces ...
... and a neighboring Lexus dealership.
Most of the cars on the street seemed to be either Mercedes, BMW, Audi, Lexus, or Range Rovers.
I started making my way toward Belle Haven, an exclusive gated neighborhood that used to be a resort community for summer vacationers from New York City. Belle Haven has been home to some prominent people over the years, including hedge fund mogul Paul Tudor Jones, Diana Ross, and businessman George Skakel.
The very first house I saw had a sign indicating it was equipped with a home security system. As I walked through the neighborhood, I saw that was the norm at most houses. The streets were quiet and lined with trees.
Some of the homes were on smaller lots ...
... while others sat apart on large swaths of land.
The houses seemed to get progressively larger the father I walked into Belle Haven.
Shelly Tretter Lynch, a real estate broker at Compass in Greenwich, said her average home sales in Greenwich range between $4 million and $10 million.
I was surprised to come across a luxury hotel in the residential neighborhood. The Homestead Inn has a top-rated restaurant from chef Thomas Henkelmann.
Rates range from about $280 to $495 per night, according to the website.
As I continued my walk, I noticed that many of the neighborhood's homes were set well back from the road and protected by gates.
Others were hidden from view behind tall hedges.
Many of the homes I saw seemed quite old, but they were very well-maintained.
I headed toward Belle Haven Club, the neighborhood's waterfront country club.
But when I made it to the club, I found I couldn't get a clear view through the hedges and fences.
With my attempt to get a peek at the country club thwarted, I took an Uber back to Greenwich's downtown area, with a plan to walk up Greenwich Avenue, the town's commercial center. The street had a charming and historic small-town feel.
But the shopping options were anything but quaint. One of the first stores I spotted was Theory, which sells $600 blazers, $285 pants, and leather jackets for upwards of $1,000.
As I strolled up the street, I spotted someone wearing the infamous Orolay coat from Amazon, the parka that allegedly originated with Upper East Side moms and went on to take over New York City. I'd go on to see three or four more people wearing it in Greenwich.
Greenwich has its own Apple store right next to upscale menswear retailer Rodd & Gunn.
All of the shops on the avenue, from Athleta to Warby Parker, looked almost brand-new.
I passed by darkened windows of a former Tesla dealership, with a sign in the window saying all sales are now online.
Many of the cars parked on Greenwich Avenue had license plates from New York and New Jersey. I couldn't help but notice how clean the sidewalks and streets were — usually a mark of an affluent community, I've found.
Luxury French retailer Hermes has a spot on Greenwich Ave.
There's also an impressive-looking Tiffany & Co ...
... as well as a Saks Fifth Avenue, the luxury department store that has its flagship in New York City.
I stopped at the local Starbucks for coffee. It seemed to be a go-to spot for informal business meetings.
It was there that I spotted the first person wearing a Canada Goose parka, although I'd go on to see several more of them throughout the day. Canada Goose parkas can cost upwards of $1,600.
... and Axiom Investors. Robin Kencel, a real estate broker at Compass in Greenwich, said about 50% of her home buyers work in finance. Bridgewater Associates Founder Ray Dalio is one of the town's most prominent residents.
After my tour of the compact shopping center of Greenwich, I started walking up West Putnam Avenue.
I passed a Whole Foods Market, which of course had several Mercedes in the parking lot.
In 2019, Greenwich was ranked the safest town in America by home security company SafeHome.org.
I started heading away from the town center to another residential area: the Putnam Hill Historic District, which was once the center of Greenwich.
Like in Belle Haven, the streets were extremely quiet and filled with large, beautiful homes.
It was a weekday afternoon, and I saw very few people walking around like I was, apart from one older couple with a dog.
My next stop was Round Hill, an area north of town where you can apparently find sprawling countryside mansions. Out here, the homes were indeed noticeably huge and set on large pieces of land.
Some were set back at the end of long driveways marked by ornate gates. A few of the houses had their own intercom systems right outside the gate.
Peeking through one gate, I got a glimpse of Round Hill Manor, one of Greenwich's great estates, according to Sotheby's International Realty. It's on the market for $22.5 million.
Greenwich is consistently ranked as one of the richest towns in America. In 2018, the average household income in its Old Greenwich neighborhood was $336,692, the 12th-highest in the nation.
Kencel told me 45% of her home buyers come from Manhattan, and that more and more wealthy city dwellers are choosing Greenwich for a vacation home. "People who might be looking in the Hamptons for summer residences are now realizing Greenwich is just 45 mins from the city," she said, adding that Greenwich has four beaches.
As I headed back to Greenwich's train station for the journey back to New York City, I definitely understood why wealthy Wall Street types and so many others are drawn to the town; after all, it's a quiet, clean, and safe place to live — if, of course, you can afford the price tag.