Okay, folks, let’s dive into my little adventure figuring out which Connecticut towns are close enough to NYC for an easy(ish) commute.
So, I started this whole thing because, well, NYC rent is insane. I love the city, but my wallet was crying. I needed a place that gave me some breathing room, price-wise, but still let me get into the city without spending my entire life on a train.

First, I grabbed a map. Seriously, an old-school, paper map. I wanted to see the distances, not just rely on some app. I marked NYC, then started circling towns in Connecticut that looked…promising. I also had Google Maps open on my laptop, just to double-check travel times.
My initial thought? Anything along the Metro-North Railroad line. That seemed like the obvious choice. So, I started looking at towns like Greenwich, Stamford, Darien, and Norwalk.
- Greenwich: Fancy, expensive, but super close. The express train gets you to Grand Central pretty fast.
- Stamford: Also pretty close, a bit more “city-like” than Greenwich, with its own downtown area.
- Darien: Quieter, more residential, still a manageable commute.
- Norwalk:A little further out, but potentially more affordable.
I spent a good few hours just poking around on real estate websites. I wanted to get a feel for what I could actually afford. Greenwich? Ouch. Stamford? Still pricey, but maybe doable. Darien and Norwalk started to look a lot more appealing.
Digging Deeper
Next, I started looking into the actual commute. Not just the train time, but the door-to-door situation. How far is the train station from potential houses? Is there parking? (Spoiler alert: sometimes it’s a nightmare). What’s the traffic like getting to the station in the morning?
I used Google Maps and entered some random addresses, pretending I was commuting during rush hour. I, added time estimates because in reality, traffic always bad and things happen.
This is where things got real. Some of those “one-hour” commutes on paper quickly turned into hour-and-a-half (or longer) ordeals when you factored in the whole getting-to-the-station-and-finding-parking thing.

My findings
I focused on towns in Fairfield County. Those seemed to have the best balance of proximity and (relative) affordability. I still loved the idea of a reasonable commute to NYC. After all my searching and calculating, I felt that these towns were a good fit. I also wanted to make sure that I could settle in to my new surroundings and that I would have things to do!