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I'm pleasantly surprised to see so many people giving props to the Philly skyline entrance--i'm a resident and am very critical of it.
A lot of it for me is just luck of the draw on building placement. Chicago's skyline feels so dramatic and sprawling due in large part (because it is) to the fact that it's 4 main supertalls (Big John, Aon, Trump, Sears) are spread out in almost 4 unique quadrants of the city.
Philly's 5 tallest are all clustered within a 2-3 block radius of each other--so, in many ways, from a dramatic view standpoint--they all work to cancel each other out. If you took them, spread them out--one on Market East, South Broad Street, etc. - it would lend to a far more impressive vista.
Of course the best entrance into Center City is from University City, going over the South Street Bridge:
LOL, you're right, that's not very dramatic because the skyline unrolls slowly over your shoulder as you drive down I75/I85. Kind of have to crane your neck a bit - not good to do while driving.
One cool Atlanta entrance is a back way I sometimes take into the city via Northside Drive. When you turn onto 17th Street you can suddenly see both downtown and midtown while approaching Atlantic Station.
One of my favorites is coming into downtown Cleveland heading east on Ohio Rt. 2. You get a great view of the skyline to your right and Lake Erie is to your left. You then pass through the Warehouse District and the Browns stadium and Rock and Roll Hall of Fame are to your left.
I just love hilly river cities, I guess, but I'll put another vote in for Pittsburgh (Fort Pitt Tunnel and W I-376 at Schenley Park), Cincinnati (N I-71/75 from Kentucky & S I-71 from Taft Rd), and St Paul (W I-94).
I love how you can see the Minneapolis Skyline before the St Paul Skyline despite it being 7 miles further away.
One city I haven't seen mentioned that is actually one of my favorites is Peoria on Westbound I-74. The way the city presents itself before going under the Fundulac Bridge is really beautiful.
Hard to get the feeling from the video, but here it is:
Chicago coming into Downtown from Metra can be impressive from a skyline view, same can be said of any expressway coming in from the west, a tour boat going through the Chicago River as all the bridges that are in sync are being raised, and finally going from south to north along Lake Shore Drive.
New York and Miami too. With New York, you see these shanty-town looking industrial areas in Newark when you arrive at Liberty, lots of industrial refineries on the way to Manhattan, then cross the Lincoln Tunnel and it's like "wow, this place is incredible". Miami's is very nice going from or coming back to the mainland on the way to Miami Beach. The small islands with skyscrapers or dense red tile roofing with turquoise blue/green water is refreshing to look at.
I posted in this thread a while back and I mentioned the Tobin Bridge approach to Boston on Route 1 South. I love the view after the tollbooth (2:15 on the video).
I also love the view from Storrow Drive Eastbound, but unfortunately there aren't many good videos of it. This one is OK, but it's a little shakey and skips the best part (through Back Bay with the Charles and Cambridge on your left, Financial District in front, and Back Bay's best buildings on your right).
One of my favorites is coming into downtown Cleveland heading east on Ohio Rt. 2. You get a great view of the skyline to your right and Lake Erie is to your left. You then pass through the Warehouse District and the Browns stadium and Rock and Roll Hall of Fame are to your left.
Entering Pittsburgh from the Ft Pitt Tunnel and from I 279 North is impressive. The downtown skyscrapers, bridges, rolling hills and rivers cant be beat.
Entering Cleveland from the turnpike to I90 into downtown is quite impressive. The skyscrapers come into view just beyond the industrial complex. It is a beautiful site.
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