The cool parts of the cool cities are increasingly decooled by people with more money than style -- Soho, Venice, the Haight, to cite a few.

Santa Fe....

Oh, Christ, Gerard, you should see what they did to the dusty old Santa Fe of my youth.

On the bleached bones of the high-water-mark of the Spanish Empire, the Cool Ones erected an adobe theme park; but not real adobes anymore. I can't even smoke a cigar anymore in The Palace Restaurant. The dingy watering-hole where the old Patrones used to broker legislative power and favors is now a gay bar.

The locals have been taxed out, but can maybe get a job busing dishes or stuccoing the fake adobes.
I console myself with the knowledge that I will see it return to near ghost-town again in my lifetime.

That would be very cool.

Boy, have you hit the nail on the head...
Healdsburg, Ca.
Formerly agriculture country, briefly cool, then finally, antique stores and poodles.
I was spray-painting on boarded-up buildings (not because they were closed down, but because they were being renovated to house the next salon/restaurant/upscale clothing store) the phrase "Go back to Marin, go back to LA, back to SF, back to San Jose...Just go the fuck away."
Alas, the Volvos, Prius' and Subarus kept coming...

Yep, that's exactly how the "cool" libs look at it: I've got mine, f*#@ you! Concerned about the "little guy"? Not on your life. Only about keeping him out of the lib's gated community and favorite restaurant. The most selfish bastard on the face of the earth is a liberal who's made it. But he's got the unmitigated gall to tell you he cares.

Gray said: "I console myself with the knowledge that I will see it return to near ghost-town again in my lifetime."

Hmm, I wonder if we know each other. I too am from that once wonderful town. Where a frito pie from the Woolworths was a treat. When what is now kitschy downtown galleries was the business center. Business men ate their sack lunches sitting on a bench on the plaza. Sears, Montgomery Wards, the old High School all sat in that 10 block square area.

Where the status of a politicians bar bill at The Bull Ring was shown by where his caricature sat on the walls. If you were current it sat near the bar, in arrears it sat in the men's bathroom. My friends mostly sat in the bathroom.

My hometown has been discovered three times in my lifetime.
1. Trust babies out of Chicago and NYC played at art and being hippy.
2. The new money came out of LA and SF.
3. The latest is the Dallas horsey set who built Las Camapanas that won't let the locals on the property unless they have invited work to do.

Santa Fe - where NIMBY was invented I think.

And don't you know? "It's every ones Fanta Se to live in Santa Fe!"

In terms of "place" you are spot on. The monied yups have pretty much taken over cool places.

But "Cool" for me has changed in meaning over the years. In the old days artists, musicians, mind expansion, lifestyle experimenters were cool to me. You know, being hip. Then came a time when political activism was cool. Cool for me now is someone who is genuinely themself, living with an open heart, spiritual awareness, and maybe an old-timey, earthy, connection to the history of a place. I know it's an subjective thing, this cool.

But when cool becomes contrived, it is NEVER cool.

I'm sure that is why almost everything about Obama grates on me.

Please let the cool people with money know that Michigan is more than willing to have them coolify its old gritty keeping it reeal industrial cities.

The sad thing is that Western Michigan is really nice.
The beaches are beautiful, a lot of the small towns along the coast are really nice, and the people are nice, too.
The Anti-industrial revolution has killed Michigan, just as it is killing Ohio. There is no road back, I'm afraid.
But Michigan has WINTER. Which might make it too cool for the cool ones. Heh, as they say in Knoxville.

""""Once you kill that spirit with predictable motion, you don't have cool but kabuki. And moving in that dead dance you don't find hipsters, but cold corpses twitching in a jerking dance of post-mortum effects."""""

For some reason, that brings to mind the 12-year slow-death-spiral of Michael Jackson. It's remarkable how different kinds of decay are still guided by the same underlying algorithm.

""""Nobody with a net worth south of $30,000,000 is allowed to actually live by the ocean""""

I was in high school in the mid 60's when my Grampa died. He and Nana had retired on his Con Ed pension to a cottage in the the dingy little seaside town of Keansburg, NJ. It was splendid dingy for a kid, and we didn't need $30 million to be at ocean's edge. After the service, funeral, and Irish wake, we kids went out to the beach, and had footraces, and long-jumped, and tried to see who could toss a big chunk of driftwood the farthest. Inadvertently, we siblings and cousins were celebrating Grampa's life and honoring his death with ancient funeral games. It was a gorgeous, splendid day, and the first time I seriously tried whiskey, my Grampa's favorite. Nana was now free to become Keansburg's best female bowler and pool player, and have a blast by the sea -- on a Con Ed pension.

Hummm... you're right, which was why I said "(Unless grandfathered in by, well, your grandfather and you'd better be able to scrape up the jacked up property taxes too.)"

The problem with "cool" towns like Westport, or Litchfield, or Ojai is that the people who move in aren't really moving in. They have their place in the city and this is just a place to impress their friends.

Pretty soon the housing prices go so far up the natives can't afford to stay in their hometowns anymore. Meryl Streep complained to the mayor of a Northwest Connecticut town where she had her weekend place that there should be a law that the townsfolk shouldn't shop on Saturday and Sunday. They were making it so crowded the weekenders couldn't get their shopping done.

In Kent they could hardly get enough people to run the volunteer fire department because most of the "residents" were back in the city all week. They didn't want to volunteer anyway--they weren't there to work, they were there to pose and posture. They sure know how to lead inauthentic lives in good clothes.

There are beautiful places all over Michigan. And if you're looking for that country-living-within-the-city feel, Detroit now has plenty of wide open spaces. (I wish that was a joke.)

Savannah was a cool place growing up in the sixties. Isolated, indolent, Spanish moss-draped, with twin circulatory systems of saltmarsh creeks and Southern Gothic craziness. Now it's a freaking mob scene of tourists trying to find the pulse of the supposedly ubiquitous gay scene. I'll never move back.

Hmm, I wonder if we know each other. I too am from that once wonderful town.

Hey, I wonder! I'm actually from, and still live in, Placitas. They did the same to this place. It's overwhelmingly wealthy, white, female and liberal now, but I live in the old village where it is still pretty insular and hispanic--it still counts to be "a local" here.

Where a frito pie from the Woolworths was a treat.

Oh, yeah! My dad usta get a 12 of Coors and a frito pie and I would get a little toy and a comic book there and we would spend the day splashing around in the Galisteo near the coke ovens at Waldo.

Where the status of a politicians bar bill at The Bull Ring was shown by where his caricature sat on the walls.

That was the bar I was talking about. It'll be back. I'm only 40; my little son is only 2. We can outlast them.

Sometimes,very late at night when the moon is up, after the boutiques and wine bars close, the old calaveras still come out in their severe black suits and bright dresses on the Santa Fe plaza.

First place I thought of was Sante Fe. Pre-Katrina French Quarter, too.

Growing up for a time in Montana gave me a wealth of really cool places, which have since become way too cool for the peasant likes of me. Bozeman, Kalispell. The only cool place left is Great Falls, and no one hardly ever goes there anymore, since it isn't cool.

I spent several years of my teens in that area of CT you wrote about in your post. As one of the sub-30k a year club it was very surreal. There are many things looking back that make my head spin but the one that has been front and center lately has been the sense of entitlement that the affluent have. Truly the same emotion springing from the same source as a 3rd generation welfare recipient. I bet if Ms. Streep had ever been confronted about the absolute foulness of her request she would be offended and clueless because of course of course she is a GOOD person, she just wants the community to accomodate her and the others like her....

You see it in the endless zoning laws and restrictions on building thrown up across the landscape until nothing can be built for less than what can be raised by a consortium of rich developers.

The supreme irony is that what is built on that land, by the consortium of rich developers, is built of cardboard and staples and frozen snot. You couldn't pay me to live in most of those McMansions.

Michigan cool is mainly on the west side - Traverse City, Petosky/Charlevoix. For the working locals "a veiw of the bay is half the pay" is a common saying.

Working class people would do better to migrate to the east side of the state. Pay is at least the same and cost of living is much less.

Had a shipmate during my Navy career whom liked to wear his sunglasses inside the ship. Commanding Officer came to radio central one morning to check his messages. Our chief petty officer asked shipmate "hey, why do you always wear your sunglasses inside?" CO looked at chief and spoke for shipmate, saying, "because it is important to be cool." The good ship USS Charles F. Adams (DDG-2).
Long gone from fleet.

I guess you must be on vacation, too, Gerard.

I grew up on Long Island during the fifties and sixties. Mostly farms, woods, Grumman and its suppliers. During the summers when I was 15 and 16, my friends and I would drive out east to the Hamptons and camp on the beach overnight. Yes, I said camp on the beach overnight along Dune Rd. There were large mansions along the ocean then but it was old money. The old money people treated the locals fairly and never tried to keep any of us out. Then the Hamptons became hip. Now you'd be arrested for even attempting to sleep on the beach overnight. All summer the "cool" set treks from NYC out east to party. No locals need apply.

You call someplace paradise,
kiss it goodbye.

The concept of "cool" has always eluded me, and I have never spent much time or effort pursuing it. I have no interest in going to a particular restaurant, say, because it's "trendy", whatever that means. But if I hear the food is good, I'll give it a try. Same with a nightclub or vacation spot. "Cool" doesn't interest me. Good music and pleasant surroundings do. And if I have to pay more than I think it's worth, I'll find another place to go.