It might shock you at first, but New York City’s Upper West Side could be considered one of the “best small towns to live in” in the United States.

In fact, as a native New Yorker and someone who loves that city and also other large urban areas, it is the small town feel of individual neighborhoods that I like the most. After all, very few of us would want to live in a Times Square-like environment.

Rather, for most of us, it is the feel of “small town life” that we crave. That makes us feel at home and comfortable and relatively safe. Where we raise our kids. Where we make friends. Where we live life.

For those reasons, the Upper West Side has numerous benefits making it one of the best small “towns” to live in in America.

The entrance to Central Park from West 81st Street leads toward the Delacorte Theater
At the entrance to Central Park at West 81st Street. (I took this photo and none of the people knew I was taking it; it was unposed.)

Central Park

Most small towns either have a park or are in fairly rural areas. The Upper West Side, while it’s not in the latter category, boasts one of the undeniably best parks in the world — Central Park. (Which of course used to be the rural area of New York City prior to the 1850s.)

This asset alone — a 840-acre paradise — adds to the Upper West Side being one of the best “small towns” to live in.

best small towns to live in

Upper West Siders have direct access to:

  • Turtle Pond
  • The Central Park Reservoir (for jogging around and also for taking amazing sunset photos)
  • The Great Lawn and Belvedere Castle
  • The Delacorte Theater
  • Tavern on the Green
  • Sheep Meadow
  • The Ramble
  • (a little walk across — barely a quarter mile) The Bandshell
  • The list could go on…

Cruelty-Free Beauty Box

Central Park walks | “What is a desire path?”

“What is a desire path?” you small towns to live in

Ever since the nonprofit Central Park Conservancy partnered with the city in the 1980s to clean it up, the Park has been dramatically more beautiful. Coming with that are small fences with signs that say things like, “Area closed for seeding” and so forth. That’s all well and good.

Now and then, one wants to wander off the concrete and feel earth. Most of us get that itch.

The city — our apartments, our sidewalks, the subway, the bus, our offices — have hard, unforgiving, surfaces underfoot. We long for ground and grass.

Also called “desire lines,” desire paths are those “grooves” we create by walking between two paths already determined for us. We saunter off, like Thoreau once wrote about in his essay “Walking.”

Of course, New Yorkers, much like college students on a strict schedule, use desire paths less as ways to “walk in the holy land” (literally, saunter) than to get from point A to point B via route C, the hypotenuse.

Riverside Park

best small towns to live in

We don’t have occasion to go into detail about Riverside Park, but this gem situated between Riverside Drive and the West Side Highway is almost like a private park for Upper West Siders. Few tourists know about it and, if they do, they want to understandably spend their time in Central Park.

Food. Food. Food.

Pizza and bagels.

While New York is known for many things that have scale as the defining feature — Broadway shows, Wall Street, Times Square, Madison Avenue, even Central Park — it is the food offerings that often make the Upper West Side feel like a small town.

H&H Bagels

New York is so known for bagels that when you move anywhere else, this — and pizza — is what you miss the most.

The Upper West Side has long been known for its excellent bagels, including:

  • H&H Bagels — This used to be on 80th and Broadway, across the street from Zabar’s. It closed and left its only retail location down in the 40s near the West Side Highway. Very unpleasant. Now it has reopened at 526 Columbus between 85th and 86th Streets.
  • Zabar’s — good bagels. Fairly fresh.
  • Absolute Bagels — in the Manhattan Heights neighborhood on ~107th street. Just south of Columbia University. If going on a weekend, get there early. It’s crowded.

Pizza is harder to pin down to just a few small towns to live in

So many restaurants and pizza joints have great pizza. Here are a few tips:

  • Avoid pizza places that use the words, “Famous Ray’s ___” or “Ray’s” in the name. These are a dime a dozen.
  • According to SliceTruck, each slice should have an approximate arc length of seven inches and a radius of nine.
  • This length is why you fold it lengthwise and eat it starting at the point.
    • Do not eat part of the crust first.
    • Do not slant it or grease will drip.
    • Feel free to use the white paper plate to reinforce it underneath but don’t place the plate on your pants. You will have a grease stain.
    • You can walk on the sidewalk and eat your pizza — end first, level bites — people do this.
    • Do not take a paper napkin and dab the grease off it before eating, as a friend of mine once did, angering his dining partner.

This is all in good jest.


The myriad places with sidewalk cafes along Amsterdam and Columbus Avenues on the Upper West Side definitely make it one of the “best small towns,” because you’re likely to run into a friend. (And get amazing food.)

And the neighborhood has some of the best coffee anywhere.

The Ansonia Hotel

The “Hotel Ansonia,” now The Ansonia, is a classic Upper West Side building across the street from Fairway, to the south, and catty corner to the Beacon Theater (whose bright lights at night Ansonia residents have complained about at community board meetings).

Completed in the first years of the 20th century, the original owner, a copper heir, used the roof for limited farming, and he had animals next to his private apartment. (Quite green of him, eh?)

Famous residents over the years were Babe Ruth and many composers and musicians. In the late 1970s, its basement was used for an infamous swingers’ club called Plato’s Retreat, which used to broadcast on early cable TV.

This building makes the Upper West Side distinct both architecturally and also in the stories it has to tell, both heroic and lurid.

One of the best small towns to live in?

best small towns to live in



When we lived there — on 84th Street between Riverside Drive and West End — we had everything we needed within a five-block walk. Groceries, laundry, kids school — yes, we walked them to and from school each day! — movies, church, and — mostly importantly, good bagels and pizza.

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