"Upscale and relaxed small town"
I bought my charming, historic house in 1999 and I have never regretted it. The town is beautiful and very well maintained. Dining is on par with the big city and dont let the country-ish look of the area fool you; this is a very sophisticated area where many highly educated and successful people have opted to live. Its cultural and open to new comers. The LGBT-Q and artsy presence is clear and welcomed. Moreover, and to my liking, there is a very clear and stark absence of McDonalds, malls or the markings of prefabricated suburbia. The Taconic State Parkeay is a gorgeous pleasure to drive on, almost always. The whole area has a certain New England feel to it even if it is New York. But, good luck getting a solid, professional job in that area and, alas, this problem is not to be solved by commuting to Albany or even White Plains. These are hard commutes in the winter. The fall is spectacular in the Rhinebeck area and winters are COLD, real cold: single digits and into the negatives with plenty of precipitation. Hence, driving 50 miles a day each way is a job in itself. Many people in that area, Rhinebeck, Clinton, Stanford, Milan just pack up during winter and live down South in places like Florida, St. Simons Island, even the Carolinas. So, only move up there if your job-finances are set. This is not a bargain place in which to live. Its a wonderful town, area, and I highly recommend it.