Lodging was the biggest challenge. To cut costs in half, we stayed home Friday night and left early Saturday — it’s not like we were headed upstate for the night life. Our original plan to stay at the two-room Costello’s Guest House in Hyde Park, the town that is home to the Roosevelt-Vanderbilt National Historic Sites, was thwarted when the owner, Patsy Costello, told me she wouldn’t be hosting guests: she was working at the Regina Coeli Parish Arts & Crafts Fair on Saturday afternoon and had to fill in as organist at a hospital chapel in Poughkeepsie Sunday morning.

But she gave me the number of Dot Chenevert, a retired florist who in October opened the Greener Oak Guest House (thegreeneroakguesthouse.com) at her Hyde Park home. Ms. Chenevert, whose name is French for “green oak,” cheerily told me both of her two rooms were available. I reserved the smaller one, $75 plus tax, figuring if no one took the other one, we’d be upgraded. We were, to a spacious room painted sage green (by her husband, Paul, who renovated the wing for guests), as well as a sitting area, coffee machine, television and fresh flowers. Dot’s years as small-town florist had imbued her with the perfect demeanor for hosting, and I made a note to favor innkeepers who were ex-florists over, say, ex-morticians, on future trips.

We arrived in the area midmorning, and immediately headed out on a self-devised tour of the area’s farm stores (ending with that mini-lunch in Rhinebeck). At Fishkill Farms, we bought a carton of pint-size, red-blushed Seckel pears left over from the fall harvest, about two pounds for $5, along with a half-gallon of apple cider and fluffy, greaseless $1 cider doughnuts. Then we went to Sprout Creek Farm for a free and personalized sampling of their cheeses (we tried all six, creamy and crumbly, smooth and sharp, cow and goat) and Caroline persuaded me to buy a $7 wedge of a firm, bold-flavored cow’s milk cheese called Bogart. Then we walked around to visit the animals, as the farm encourages. A gang of turkeys ruffled up their feathers as we arrived, as if we were their biggest threat during this pre-Thanksgiving week.