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[quote=Anonymous]We lived in Kingston for a few years, and recently moved away.  The HV is a patchwork of small towns, and each of them is remarkably distinct in having their own culture and vibe.  Here's my personal take:

Kingston:  interesting mix of blue-collar and newer transplants from NYC/Brooklyn.  Strong arts and music scene, but also an undercurrent of wealth disparity and resentment between long-time families and newer arrivals.  Politically pretty liberal/progressive, and very LGBTQ friendly.  Great access to both the river and the Catskills.

Woodstock:  smaller, more isolated, but also wealthy and very progressive.  Overrun with tourists in the summer.  Beautiful location, but I personally wouldn't want to live there due to the congestion and "preciousness" of the town.

Saugerties:  more traditional, and blue collar.  Lots of families, a bit more conservative but probably not LGBTQ unfriendly.
  
New Paltz:  a small college town, very progressive.  Surprisingly lively given its size, but also very congested with traffic.  Good access to the Shawangunks for hiking/climbing.

Rhinebeck:  the east side of the Hudson was always the "old money" side, while the west side had the railroad and the blue collar jobs.  Hence Rhinebeck and Hyde Park are still "prestige" locations.  Politically progressive, but also very privileged.  I joked to my partner that the High School kids holding up Black Lives Matter signs in Rhinebeck had probably never met a black person.  Red Hook is a little more middle class and good for families.
 
Poughkeepsie and Newburgh are the larger cities in the region, and not generally too good (especially Newburgh) with higher crime and unemployment.

Beacon and Hudson are two towns that have attracted a big influx of NYC transplants, causing rapid gentrification.   Beacon is within reach of the NY commuter railroad and hence has seen prices spike.  But its a lively town with a big arts scene.  Hudson isn't my favorite spot - it's got one street with lots of Bougie shops and restaurants, but the surrounding blocks are blighted, so it feels very odd.  It's also fairly isolated being another hour north of NYC.

If you are looking for really small towns, Rosendale, High Falls, Marbletown, and Gardnier are all viable options.  Rosendale particularly is very funky and hippy-ish.

The "red" towns are dotted here and there.  Esopus and Lake Katrine are notably more conservative. [/quote]

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