Boston:
9/10... I don't think skyline means jack in terms of urbanity in downtown areas (Look at London, Paris, Rome, Washington DC... even Boston's Best neighborhoods are mostly low-rise). While it's pretty to look at from afar (and sometimes up close) skylines really add nothing to a city-scape (possible exception being the canyonization in Manhattan).
That being said, Boston has a terrific downtown fully of all sorts of restaurants, shops, and nightlife. Some of the nations best museums are here and the city is obviously teeming with history. The ancient street grid allows for interesting, unique vistas from every corner. A mix of periods and architectural styles is quite pleasing to the eye. the Common, Public Garden, Post Office Square, Copley Plaza, the Commonwealth Mall and The Fens are a few of the best public spaces in the U.S. Public transit and an amazing pedestrian friendly nature make Boston one of the best downtown areas you'll ever visit. I'd give it a 10/10 but I went with 9/10 becuase i don't think anywhere is perfect.
New Bedford, Massachusetts: This is the small city (about 95,000) I grew up near in South Eastern Massachusetts. I give its
downtown a 7/10. There is nothing in the way of high-rise (The highest is 16 stories), but it has a dense, historic downtown complete with some incredible architecture and cobbled streets. This city is also teeming with history as it was the worlds largest whaling port (and the basis of Herman Melville's "Moby Dick") and a key cog in the underground railroad (Fredrick Douglas settled here). The downtown today is in the middle of a HUGE revitalization (you woudn't want to visit 5 years ago) as the city is now the richest fishing port in the country (in terms of value of catch... 9 years running). There are great restaurants, fantastic shops and art galleries, stunning architecture, good nightlife and some entertaining musueums. Not to mention it's on the beautiful Southern New England coast with views of the Elizabethan Islands and Martha's Vineyard.
Some downtown
New Bedford Photos:
Looking North on Purchase Street Downtown:
South on Purchase looking at Olympia Tower... A surprisingly successful facadectomy:
Looking towards Union Square in Downtown... Star Store Building on the left:
Star Store: Home of some of UMass dartmouth's Downtown NB Campus:
Union Square Decorated for the holidays:
A nice store on Union Square:
Webster Bank Building on the corner of Union and Pleasant:
Looking North on Pleasant St. Towards City Hall Square:
City Hall and City Hall Square with the "Holiday Tree"... they had a nice concert later in the evening:
closeup of the City Hall Christmas Tree:
City Hall Square (concert setup):
Clock and Santa's Sled across from City Hall on Pleasant:
Looking East across pleasant st. towards William St... unofficial entrance to the Whaling District:
Looking North on Pleasant St:
The Decor on William St. looking towards the whaling district and the harbor:
Detail on a building on William St:
Cherry Building- an Art Deco Gem on the corner of William and Purchase St:
looking North on Purchase St from William St:
Looking South on Purchase from William St:
Herman Melville Square in the Whaling District:
Shops on Acushnet Ave. in the Whaling District:
Dover Street:
an old Bank:
Freestone's City Grille... good food even better drinks:
More shops and galleries:
Whaling Museum entrance and the end of William St (another old bank in the background):
Johnny Cake Hill, Whaling Museum is on the left:
North Water St. in the Whaling District (Cafe Balena on the right serves great Sicilian cuisine):
Nice older buildings:
Looking down towards the Harbor... you can see some of the fishing fleet:
Again, towards the waterfront:
Looking West (away from the harbor) on Front St:
Cork Wine and Tapas on Front St (fantastic, btw):
Catwalk Bar and Grille on Union St... lots of fun on their roof deck in the summer:
Looking West on Union St... Ocean Explorium is the building with the Columns on the left:
The tree at the Ocean Explorium:
Union Square Clock on the Ocean Explorium:
Star Store again:
Zeiterion Theatre:
Olympia Tower:
Old Facade below Olympia Tower: