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I've been living in the area for two years now and go up to Highwood regularly. It's about a two minute drive from where I'm typing. My impression of Highwood is that it's the epicenter of fine dining for the "Northern" north shore. I'm not kidding. Every other restaurant has valet parking. French, Italian, Nouveau, Irish, Indian, Mexian-- you name it, it's up there.
They also had a farmer's market on Wednesday nights this past summer that was particularly nice-- fresh pasta, exotic cheeses, live acoustic music, baked goods, party lights, the whole shebang.
Highwood does have a larger Latino population, but there's no "hood" vibe to it. Lots of families, blue collar workers, there might be slightly higher crime, but I wouldn't be afraid to walk on the streets alone at night. Everybody is really friendly. I guess what I'm saying is that I find the whole "over run," "excessive alcohol consumption" remark above alarmist and unfair.
The northern end of Highwood going into Fort Sheridan is a bit less tony, but still nice. The new development at Fort Sheridan is fairly upscale, while much of the surrounding area is the community that supported the original, functioning military base (which is still there, although smaller). That part has neat old taverns, taco stands, hot dog stands, Italian bakeries, 70's throwback restaurants-- "regular Joe" kind of stuff-- and for my money, food every bit as good as the valet restaurants.
My impression is that Highwood also has a sizable Italian American population-- there's a TERRIFIC small Italian grocery store with homemade pastas, sauces and sausages that is worth visiting just for the great smell that meets your nose when you walk in the place.
My bottom line, check it out for yourself. I think it's a decent area with access to a lot of great amenities.
FYI-- as a resident of either Highwood or Fort Sheridan, your kid will attend a Highland Park District 112 School, so visit their website for info on that. It's a good school system.
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