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  • Writer's pictureAdam Hlasny

My Favorite US and Canadian Skylines (Part II)

Hard as it may be to believe, it's been nearly two years since my Big City Skylines post. Even harder to believe, that post, arguably the least travel-related on my TRAVEL blog, is the most popular one. Given this fact, and my enjoyment in rating skylines, I'm back for Part II. This time, though, we'll look at "medium-sized" cities, with populations between 250,000 and 500,000.

While this is obviously a subjective exercise, I've tried to level the playing field by rating each skyline on a 30-point scale. As a reminder:

  • Variety of buildings (10 pts): when I look at the skyline, do all the buildings look brown, square, and the same height, or is an appealing mix of classic and modern lines?

  • Overall robustness of skyline in relation to city population (10 pts): Does a city of 350,000 people have 50 tall buildings or 2? Of course much of this has to do with regional development patterns, etc., but for now we're focusing on skyline aesthetics.

  • Wow factor/personal opinion (10 pts): Is there a building that impresses in its height or architectural significance? Is the city setting magnificent (think San Francisco) or mundane (Omaha)?

Without further adieu, heeeere we go:

HONORABLE MENTIONS: St. Petersburg, FL (16/30); Long Beach, CA (17/30)

10) Orlando, FL (18/30)

Orlando's skyline is solid but ultimately forgettable. There's a decent variety of buildings, but none of them exceed 450 feet, and despite being a fast-growing city, nothing super tall has been built since 2008, a bit of a head-scratcher. For a place as dynamic and now world-famous as Orlando, I'd almost expect more.

7t) Minneapolis, MN (20/30)

The Minneapolis skyline is very solid and upstanding - just like the midwestern values within. Its downtown cluster of buildings is compact and attractive, if a bit homogenous at first glance. With three buildings over 700 feet, it certainly punches at or above its weight for its population.

7t) Tampa, FL (20/30)

While Tampa's tallest are about 200 feet shorter than those of Minneapolis, this skyline manages to wrestle its way into 7th place for its clean, modern look, as well as its beautiful waterfront setting.

7t) Cincinnati, OH (20/30)

Cincinnati completes the three-way tie for 7th place with a great mixture of old (Fourth and Vine & Carew Towers, from 1913 and 1931, respectively) and new (Great American Tower, tallest in the city, from 2011). A view from the river that includes both baseball and football stadiums make this a very worthy contender in medium-sized skylines.

6) St. Louis, MO (21/30)

St. Louis' skyline is very similar to Cincinnati's in many ways. It edges ahead of the three-way tie, though, with the seminal Gateway Arch. Love it or hate it, St. Louis boldly encouraged this iconic structure to be built that now makes its skyline instantly recognizable. I was fortunate enough to ascend to the "top" of the arch in 2015 - its 50th birthday - and remember being in awe of the exceptional design, taking copious photos from below and above.

5) Honolulu, HI (22/30)

Aloha Honolulu! This skyline was a bit tough to evaluate - on the one hand, there is a massive amount of skyscrapers - 26 over 400 feet! Also, the twin backdrops of Diamond Head and the glimmering Pacific are hard to top. So why did Honolulu finish in 5th place? A strict height limit of 450 feet* ensures that A) there are no standout tall buildings, and B) there are dozens that look similar, architecturally and height-wise. Further, the skyline sprawls for what seems like miles in every direction without much of a core area, diluting the overall effect further. While 5th place is not too shabby, I'd almost have expected better from a city whose very name evokes exotic fantasies.

*The article linked above (from 2014) mentions this height limit being raised to 650 feet. While this could clear the path for some more impressive buildings, might it also interfere with the view of Diamond Head, the whole reason for the height limit in the first place?

3t) Jersey City, NJ (23/30)

From Hawaii to... New Jersey. What a transition! How does NYC's tiny tot brother across the Hudson vault into a tie for third place? Well, because of an enticing combo of modern towers, four of which (all built since 2004) are over 700 feet. This banking mecca, nicknamed "Wall Street West" has grown into a skyscraper powerhouse, belying its population of just under 300,000. If that weren't enough, its towers are sleek, architecturally interesting, and sit pretty right on the river. Oh, and the views of Lower Manhattan across the way aren't too shabby either.

3t) Cleveland, OH (23/30)

Back to Ohio we go. Cleveland rocks its way into our co-bronze medal position with an excellent mix of buildings including the massive 947' Key Tower (tallest on this list as of 2022), and the Terminal Tower, a 1930 gem that was second-tallest in the world when completed! A gorgeous setting aside Lake Erie and the - now much cleaner - Cuyahoga River puts this skyline solidly among the best on the list in my book.

2) Miami, FL (24/30)

And the silver medal goes to... Miami, a South Florida skyscraper mecca with a powerhouse skyline. Like Honolulu, the skyline sprawls up the coast. Unlike Honolulu, Miami's top towers are nearly twice the height. Miami's 'scrapers are so multitudinous that its skyline is considered the 4th largest in North America and 28th largest in the world! Why on earth, then, is it in second place? Because size alone isn't everything. It's super impressive, but hardly compact. Also, other than its size, it doesn't have a signature building or architectural standout.

1) Pittsburgh, PA (25/30)

Wait, what: the Steel City? Don't you mean the Steal City? Shouldn't impossibly glamorous Miami have won? Well guess what: this much-maligned Western PA metropolis is my first-place winner, and here's why: an excellent mixture of towers (10 over 500 feet is impressive for a city best known for past industrial might), and compact, instantly recognizable cityscape. The very best part though? Pittsburgh's amazing setting, wedged in a triangle between three rivers.

I have visited the city twice (2012 and 2020). Approaching the city from the west, one is treated to the most magnificent introduction to any city I've ever seen. One is driving amid rural forested hills that could be nearly anywhere. You enter the Ft Pitt Tunnel and emerge, less than a mile later, to an urban explosion. Crossing a stalwart, yellow-painted bridge, there is too much to take in during those few seconds of awe. Three rivers, two professional sports stadiums, forested hills, and architecture ranging from classic to cutting edge.

On paper, this may not be the most impressive cityscape, but my goodness does it make an impression. Therefore, humble Pittsburgh is my favorite medium-sized North American skyline, like it or not.

The very respectable skyline of Halifax, NS

NOTE: You may have noticed that no Canadian cities made my top 10. For what it's worth, both Halifax, Nova Scotia and London, Ontario narrowly missed being hono(u)rable mentions. I also discovered that many Canadian cities in this population category are actually giant Toronto (Vaughan & Markham) and Montréal (Laval, Longueuil) suburbs without much of a proper skyline. For what it's worth, 3 of my top 10 big city skylines were Canadian (Montréal, Calgary, Toronto). Far be it from me to just pick on Canadians...


OK, before we get our britches bunched, I'll offer the same disclaimer here that I did in the first skyline post: listing a city here does not mean I have anything against it, only that it does not have any discernible cluster of tall buildings that could be considered a skyline. Basically, these are all gigantic, low-density suburbs whose populations have ballooned into the medium-sized city category. I won't go into detail on each because there's really nothing much to say. Here's the list that really should receive an N/A score rather than a shameful 0/30 on my scale:

  • Arlington, TX

  • Aurora, CO

  • Chandler, AZ

  • Chesapeake, VA

  • Chula Vista, CA

  • Gilbert, AZ

  • Henderson, NV

  • North Las Vegas, NV

And there you have it: large and medium-sized US and Canadian cities rated. If this post gets some love, I'll consider doing a smaller cities list as well (100-250k population perhaps).

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