Originally Posted by ardecila
I understand that Winnetka has two downtowns (Highland Park too, or three if you count Braeside). Hubbard Woods is somewhat small but it's well laid out and oriented around a beautiful town square at the train station. Green Bay Rd is lined with many unique and successful businesses and the street has great architectural character with mostly 1920s Tudor and Neoclassical.
From my perspective, Hubbard Woods is more beautiful than downtown Lake Forest, which is a weird eclectic architecture and purposefully auto-oriented, whatever that meant in the 20s. For the most part, though, the North Shore is pretty good urbanistically.
Glencoe's downtown is not even worth considering for the business mix, architecture, or pedestrianism. Lake Bluff and Ravinia do much more with less.
Hubbard Woods is tiny. You could isolate a comparable strip from any larger North Shore downtown. I certainly wouldn't categorize it differently than Glencoe or Winnetka. In fact, I'd rank Highwood above Hubbard Woods; it has a working class charm that's unique to the area and more vibrancy after 5pm than most North Shore locales. (Lots of bars and restaurants. The Italian heritage is strong, though not as much as it used to be during Highwood's heyday when Fort Sheridan was more active.)
Braeside is not a downtown, just a Metra stop with a couple businesses across the street. There's a weird little area just to the west of Route 41/Skokie Highway at Deerfield Road that has more claim to title of Highland Park's "third downtown" than Braeside.
If we're just talking the North Shore, I'd say downtown Highland Park easily outranks all the others after Evanston. There are some questionable planning choices and architecture styles, to be sure, but some really great ones, as well: underground parking, higher density (and mixed income) housing (something you won't find much of in the rest of the North Shore: limousine liberalism and whatnot), mixed use. In general, the city has taken more risks, and the overall result is an interesting mix—most often nice, sometimes endearingly quirky. When you consider the institutions housed there (the high school, a middle school, and an elementary school; the city hall; the library; the historical society; an art center—"The
Art Center") and some of the businesses (Saks, Anthropologie, E Street, Paper Source, boutiques, spas, bakeries, chocolate shops, an art house movie theater, a second-run theater, Sunset Foods) and restaurants (Once Upon a Bagel, Michael's, Stash's, Love's frozen yogurt, Walker Bros.), IMO, it's hard to find anything else in the area that comes close.
Originally Posted by ardecila
It's often difficult on the North Shore to decide whether each downtown feels nice because of good design and planning, or because really wealthy people poured money into them to avoid embarassment.
Really? There are plenty of wealthy suburbs with shit downtowns. Deerfield had an opportunity not too long ago to make their downtown more inviting but totally blew it with the arrangement of the massive amount of surface parking they installed.
ETA--sorry, TUP, missed your post.