I spend a lot of time in Woodstock, New York and I LOVE these three spots mentioned in this article I wrote for Yahoo! about great meals in the Catskills. Here's the link for restaurant recommendations: http://www.associatedcontent.com/article/6114890/valentines_day_din...
And if you want to stay the night in Woodstock, DEFINITELY check out the Woodstock Inn at http://www.woodstock-inn-ny.com/. I've stayed here and can personally recommend it for its charming, romantic rooms near a gorgeous river view.
Enjoy Woodstock on Valentine's Day!
Best,
Jennifer
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