I've been driving along Route 44 west of the Taconic once a week and have a few chowy recs here:
Pizza--there are about six pizzerias along the way and we've been sorting through them to find the best. It's definitely Poppa's Pizza in the middle of Pleasant Valley. Park in back. Not only is the slice really crisp, tasty crust, tangy sauce, overall well made, but each slice covers twice as much real estate as the typical slice elsewhere. Reminds me of the Yogi Berra-ism: when asked how many slices his pizza should be cut in, he said, "Cut it in four, I'm not that hungry."
Shopping: Everyone knows about Adam's Fairacre, I guess. The whole world is there Saturdays. Also, Quattro's is right along the way. Hit their freezer and salumeria.
Right across from Adam's is a great place, Arlington Wines and Liquors. Prices are about 30% less than other local liquor stores, and their selection is awesome. A wine I buy for $18 in Pine Plains is $13 there. They might also have a case discount, and I think they deliver.
There's a restaurant supply store along 44 between PV and Pough. Anyone know anything about it? Haven't stopped there yet.
Also, across from Poppa's is a Greek place called Apollo's Cafe. Anyone have any scoop on that?
I'm trying to branch out, but my son is wild about Poppa's now--they have great old wooden tables, cool pizzamen, and they always have the football on.