My favorite cities are my favorites for a reason. They are one-of-a-kind destinations with skylines that can’t be mistaken for anywhere else. There are too many cities whose skylines are uninspiring, with diminutive downtowns, suburban strip malls full of cookie-cutter chains, and little uniqueness. My favorite cities on this continent stand out because they are outstanding…in character, reputation and design. They don’t blend in; there is nowhere else like them. You, no doubt, have your own favorites…and deservedly so…but hear me out…

Driving eastbound on the Massachusetts Turnpike (I-90) into Boston gives me the impression that I am going to drive straight into the iconic Prudential building. But as I come closer and enter the tunnels heading into downtown, I’m suddenly faced with all kinds of choices, from the Boston Common and Public Gardens to the city’s distinct landmarks and historic sites. Flying into Logan over Boston Harbor, I can see south shore towards Quincy and the Cape, westward along the Charles towards MIT and Harvard, and north shore towards Salem and Gloucester. From downtown, I can take in the waterfront, the Bunker Hill Monument, the Zakim Bridge, the Hancock and the Prudential, Fenway Park, and so many other one-of-a-kind structures. When I’m in Boston, I know I’m in Boston! There’s nowhere else like it.


“From the windows of my office in Boston … I can see the Golden Stairs from Boston Harbor where all eight of my great-grandparents set foot on this great land for the first time. That immigrant spirit of limitless possibility animates America even today.”
-Ted Kennedy

“Massachusetts has been the wheel within New England, and Boston the wheel within Massachusetts. Boston therefore is often called the “hub of the world,” since it has been the source and fountain of the ideas that have reared and made America.”
-Rev. F. B. Zinckle

Driving west and north on the Queen Elizabeth from Buffalo, I eventually come around the curve of Lake Ontario in Burlington, and on a clear day I can see the Toronto skyline north across the water. Striking and majestic, it feeds my appetite to get closer and take in more. Approaching Toronto, the beautifully landscaped parks, the tall, imposing buildings, and the gorgeous views of the lake are unlike anywhere else. I am taken in by the CN Tower and the Rogers Centre right beside it, Scotia Plaza, First Canadian Place, the Fairmont Royal York Hotel‎ and the new City Hall (never mind the old City Hall), all marvelously eye-catching. I am told to really take my breath away, I need to take a ferry out to the islands just off the coast and turn around to take in the entire skyline on the mainland. Someday. When I’m in Toronto, I know I’m in Toronto! There’s nowhere else like it.


“The fact that over 50 per cent of the residents of Toronto are not from Canada, that is always a good thing, creatively, and for food especially. That is easily a city’s biggest strength, and it is Toronto’s unique strength.”
-Anthony Bourdain

“There are some cities that you go to that bring something out of you.
Toronto is one of them.”
-Kevin Owens

Driving in from O’Hare on the Kennedy Expressway towards downtown Chicago, I follow along the blue line railway through well-established neighborhoods as I come closer and closer to the spectacular skyscrapers of the city with big shoulders. There’s the pointy-eared John Hancock Center, the Willis and Tribune Towers, and the classic art deco architecture along State Street and Wabash Avenue. Grant Park is a celebration of the city, and the drive south on Lakeshore Drive has me immediately amazed at the awe-inspiring edifices of the Field Museum, Soldier Field and McCormick Place. To take in the waterfront, I can do so on the Navy Pier, from the Northwestern Law School Library, and on a half-four drive up the coast to picturesque Evanston. But there’s perhaps no better way to take it all in than from the air as I fly in over Lake Michigan. When I’m in Chicago, I know I’m in Chicago! There’s nowhere else like it.

Summer day in Chicago

“It is the most perfect presentation of nineteenth-century individualistic industrialism I have ever seen. Chicago is one hoarse cry for discipline.”
-H.G. Wells

“I’m impressed with the people from Chicago. Hollywood is hype,
New York is talk, Chicago is work.”
-Michael Douglas

Driving across the Bay Bridge from Oakland into San Francisco is perhaps my favorite way to enter one of my favorite cities, taking in its full expanse from its detailed waterfront to its legendary hills. There’s Pier 39 right there as I hit the mainland, with the smell of the salt air and the barking of sea lions on the rocks below. There’s the Ferry Building, The Transamerica Pyramid, the Millennium and Salesforce Towers, and Oracle and Candlestick Parks. Whether I’m driving or being driven, there’s nothing else like going up-and-over-and-down those steep San Francisco streets. It’s thrilling and humbling all at once! And as I look back over San Francisco Bay from one of those numerous summits, the spectacle of Alcatraz and the Golden Gate Bridge off in the distance are enough to make me pause and appreciate just how special a city this is. When I’m in San Francisco, I know I’m in San Francisco! There’s nowhere else like it.


“Money lives in New York. Power sits in Washington. Freedom sips cappuccino in a sidewalk cafe in San Francisco.”
-Joe Flower

“If you’re not alive, San Francisco will bring you to life.”
-William Saroyan

It strikes me that people are a lot like the cities they build. While there are various and sundry cities across North America, there are only a handful that are so awe-inspiring I know them immediately by their skylines.

Don’t get me wrong, there are times in my life when I’ve simply wanted to blend in, but people and circumstances forged me into a unique, inimitable original. Take it or leave it, at this point in life, I like standing out…not bigger-than-life in the foreground…but in a quiet, confident standing-tall-against-the-backdrop kind of way.

I want people to look at me the way I look at Boston and Toronto and Chicago and San Francisco…I want them to know me for the character and reputation that define my profile…my personal skyline…instantly recognizable. In the end, it’s not about fleeting flash and flamboyance. It’s about longstanding stature and steadfastness…what I stand for regardless of where I am situated.

I wish the same for you. May your personal skyline be unlike anyone else’s, discernible and distinct. It’s too easy to give in to the urge to blend in. Stand out. Stand firm. Be unique. Be unmistakably you.

Walter McKenzie is Senior Director for Constituent Services at ASCD, leading its affiliate, connected community, professional interest community, student chapter and emerging leader programs.

2 thoughts on “Skylines

  1. Wanting more for yourself doesn’t mean wanting less for others. Being from a small town, I appreciate the skyline of my humble beginning. AND being afforded the opportunity to travel beyond my small town has given me a deeper appreciation of where I’m from and where I’m going. I, too, want my life to as awe-inspiring as the Toronto skyline. Outstanding post!

    Liked by 1 person

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