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I’ve been tasked with organizing a friend’s bachelorette party in late April, and the plan is to spend the weekend at a house in The Plains and do some nearby wine tasting.  (We are not looking for a stereotypical let’s-get-trashed party; we are all in our mid- to late thirties and many of us, the bride included, enjoy good wine.  Ideally we would like someplace that offers a not-to-crowded experience, but there will be ten of us, so that rules out Linden and some of the others.). Does anyone have any recommendations?  (I will certainly look at many of the suggestions on this thread, but figured the potential options may have changed significantly since 2010.). Thanks! 

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RdV would be a fun but pricey option.  Their tasting and tour is now $65 per person, but the last time I did it (it was only (ONLY) $50) and there was a bachelorette party on the tour as well.  If you haven't been there, it's super high end and very well done, but they only make 2 red wines, although you may get a glass of their rose' which they make but can't sell.  They also start you off with a glass of champagne.

Delaplane Cellars is just down the road and would be worth a stop.  They have a killer view from the tasting room and usually have live acoustic music on the weekends.  They also have bread and cheese plates.

I'd avoid Barrel Oak and Blue Valley.  Both are huge places and they are very loud.  Not sure about Barrel Oak, but you can bring your own food into Blue Valley.  At least you could a couple years ago.  I'd call to verify if you're interested. 

Three Fox Vineyards is in the same area but I'd avoid it as well.  It's much smaller than the two above, but I don't think the wine compares to Delaplae, RdV or Linden.

Arterra is in the same area and has only been open a few years.  I've only been once and it was a while ago, but my main memory was that it was dark.  You drive up a road through the woods and come to the winery which also had a "deep in the forest" feel.   The tasting room was pretty dark too with no huge windows or nice view.

A little further afield is Glen Manor.  They don't serve food, but they allow you to bring your own.  They have a nice outdoor area with lots of tables and chairs.  If it's a nice day, and you have some picnic items, this would be a good place to spend some time. 

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