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Minnehaha Parkway through south Minneapolis. For about 12 miles, it follows Minnehaha creek from the waterfall through south Minneapolis, past Lake Nokomis, Lake Hiawatha, up to Lake Harriet. It's very green, lined the whole way with huge old trees and old mansions between Nokomis and Harriet. It's part of a national scenic byway, the only one in a large city.
 

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I would say Meridian in Indianapolis, from about Kessler Blvd to Downtown. Everything that symbolizes a big city can be found on Meridian
 

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Michigan Ave. is probably the best in Chicago.
 

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I can't pick just one for Chicago, so here's my finalists:

Michigan Avenue from the Carbide & Carbon building north to The Drake.

Lake Shore Drive--twice!
The stretch from Soldier Field, past the museum campus and along the park.
The "S" curve at the North End of Streeterville then between the Gold Coast and the Oak St. beach.

The Midway Plaisance when you emerge from Washington Park, see the Fountain of Time sculpture anchoring the Midway and the U of C running along the north side
 

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In Cleveland it would be Shaker Boulevard with its large apartments leading to an old urban shopping center leading to mansions all with a vintage lightrail line running through the middle of the island in the street. In about 2.5 years though, it may be Euclid Avenue as that street is going through a major renovation adding landscaping, islands and a Bus-Rapid Transit line.
 

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Though, not a boulevard, Lower Woodward Avenue in downtown Detroit has really been spruced up.







But, even that is not the most beautiful. The most beautiful would be Jefferson/Lakeshore Avenue through Detroit's waterfront suburbs. But, I have no pictures of it.
 

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Though it is a fairly short stretch and it is entirely residential, in Milwaukee I would rate Washington Blvd from US 41 to 60th St in the Washington Heights neighborhood right up near the top.
 

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boomper said:
Though it is a fairly short stretch and it is entirely residential, in Milwaukee I would rate Washington Blvd from US 41 to 60th St in the Washington Heights neighborhood right up near the top.
Actually start at 12th street and drive west on highland blvd, then make your way past harley and miller, through washington park, then up washington blvd, then if you really want to see an interesting neighboorhood drive through the washington highlands. This street is not only a very good shortcut from downtown to the near west side, but it contains some of the best examples of turn of the century german (i think) homes. Too bad much of highland blvd was converted to apartments, at least there are still some of the old mansions that can only make us guess what it was like 70 years ago.
 

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In St Paul, or the Twin Cities as a whole, the most beautiful street/boulevard is easily Summit Ave which runs from the St Paul Cathedral to the Mississippi on the other side of the city. It is the longest single street victorian mansion historic preservation district in the country. Summit is the southern boundry of the Cathedral Hill neighborhood and the northern boundry of the Crocus Hill neighborhood. I am drunk right now so slightly boastful and such but when I was in the Garden District in New Orleans 15 years ago my first thought was "Wow, this looks a lot like Cathedral or Crocus Hill if they were 30 years older and had different hordiculture. The lot sizes, density, urban pacing, and archetectual depth were very similar. They are almost entirely intact from the 19th and early 20th century and cover several dozen square blocks. That part of St Paul is home to much of Cass Gilbert's early work, it is helpful for a city to be home to a great archetect making his reputation while it is going through a major growth spurt. Sadly those neighborhoods are expensive as hell now (it wasn't always the case). I should take pictures, if I have time I will. Minneapolis use to have neighborhoods like that but they were ruined in the mid 20th century by white flight/white fear, ghettoization, and subsequent crappy redevelopment.
 
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