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It's been interesting to read this one, and I have mixed feelings about this shift, but there is an underrated aspect that I think is worth mentioning, and that is how *pleasant* it is/can be. I'll elaborate but it might be worth giving some context first.

I grew up in CT as well, but from a pretty typical working/middle class suburb right in-between Hartford and New Haven. It had a lot going for it, but it wasn't cool or pretty.

I went to Hoboken for school and then moved to NYC after - a stint on W15th street for a bit and then a decade in Willyburg, both off the Bedford stop and the less-hip but infinitely more cool Graham ave stop. When it came time to move out of the city after getting married in 2017, my wife and I gravitated towards upper Westchester since it was still commutable to our jobs in the city while being a lot more woodsy. Our search centered around Pound Ridge, mostly, and after hopping around 3-6 houses to see we'd spend the rest of the day hiking in the hills or pottering around a small town and driving twisty roads. It was nice.

The search dragged on for close to a year and we expanded into CT - my wife had no feelings about this but it seemed unthinkable to me, since I thought I left that place. But we found it - the perfect midcentury ranch on a quiet street in North Stamford, right across the border from Pound Ridge and New Canaan (literally on the intersection of the town lines) with a huge pool and facing a pond. And we spent the next 3 years there, had a baby there, spent 2020 and 2021 not cooped up in an apartment but instead going on nature walks or snooze cruises past iconic midcentury architecture and bucolic winding roads or swimming or cooking pizzas outside in an Ooni.

And that is what I think is worth mentioning about that upper Westchester / lower Fairfield county area. Sure it's rich and probably full of wankers but everything is kept SO nice that it's a really, really pleasant place to be. The secondhand effects of it are very real. It was comforting knowing my child was going to grow up expecting things to be kept nice - not full of litter and debris and cracked roads and sidewalks. A place with mature growth trees and landscaping that is oriented around the changing seasons. It's the way my wife grew up in a small suburb in the outskirts of north London, and it's something I didn't recognize I missed out on in my Very Normal American Town but appreciated immediately once I had it close.

So for a group of people that are obsessed with Pretty Things (even if they're more focused on how it looks in a photo and not holistically) and get bummed that the city just Isn't Pretty, I can see the appeal the first time they rent a car and hit the road up there. I can't blame them!

A job change for my wife to Tokyo meant selling that house in late 2021, and while this city is very, very pleasant I do still think about it often even a few years later and the change in perspective it gave me. Hence all of the words.

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I'm jealous of your old house, I remember those ranch houses with fond nostalgia (good friends of my parents owned one in north Stamford and we visited all the time)

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Just came across this—as a fellow NMHS grad who has since moved on but who still has family in town, I’ve never once heard the historic structure on the green (now depicted on the town flag) referred to as anything other than “the bandstand.” It may fit the definition of a gazebo, and the ersatz copy of it on “Gilmore Girls” might have been called one, but no one in New Milford uses that label.

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Hey Chip, that's completely untrue lol, I grew up there and heard it thousands of times. I also still have family in town and spend a lot of last summer there! It's literally referred to as a gazebo in sourced literature from the '90s: https://www.crwflags.com/fotw/flags/us-ct-nm.html Cheers — KC

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Tell that to NM Parks & Rec:

https://newmilfordct.myrec.com/info/facilities/area_info.aspx?FacilityID=14698&AreaID=14699

Tell that to the NM Historical Society selling a medallion on this page of “our historic bandstand”:

https://www.nmhistorical.org/upcoming-events/

Tell it the NM Commission on the Arts, which sponsors summer concerts there as well as the annual carol sing there, which my late father and former NMHS band director conducted for many decades:

https://www.artsnewmilfordct.org/index.html#shows

A page from an obscure flags web site isn’t exactly authoritative.

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it's so funny that you would argue about this! I grew up in New Milford and called it "the gazebo" for my entire childhood. Call it whatever you want! — KC

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Just calling it what the town calls it—happy to provide some historical context.

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Connecticut as main character! I was born, raised and educated in Connecticut (Greenwich, northern Fairfield County and Yale). My mom still lives in the town I grew up in so I visit a few times a month. It took me a long time to realize how nice it is there and how lucky I was to grow up there. I would take friends to visit and they would comment on how lovely it was and I would point out, "Yeah, but it's also very boring, all blond ladies with tennis bracelets." I liked NYC much better and lived there for 35 years. I find it difficult to think about Connecticut clearly--it's so familiar and it just is. People used to ride their horses on trails through the woods and have keg party cookouts and it sounds like it should have been fun and in retrospect it was all very tedious. I guess I'm just not a country girl.

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Norwich. Make it happen.

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Thank you for appreciating this story!!! It was a lot of fun to write, and I'm glad you saw what I was trying to do with it.

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My fiancée is from near Stamford. The next stop on Metro North is Harlem, and we regularly beat her brother to their sister’s place in Greenwich.

I’m from Seattle, and it took me a long time to realize that his place near Prospect Park is reasonably described as part of NYC.

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