Richard, a fun place with a limited but well chosen wine list is Vintage Bar and Resaurant, 171 Main Street, White Plains. They have live entertainment several times a month, and it's quite a nice venue. Food is fairly simple, but good for this type of place. http://www.vintagebar.net/
Four of us went there last April for an English folk rocker, and had a ball.
A fascinating restaurant with a limited but lovely wine list is Blue Hill at Stone Barns in Pocantico Hills, about eight miles from White Plains. Located in the Rockefeller Estate -- the food is excellent. http://bluehillstonebarns.com/
A great place for Mediterranean food in the downtown area is Trotters -- http://www.trottersny.com/index.html
Ernani L. Silva is the wine director and he maintains an outstanding wine inventory.
White Plains is a town that is coming on fast with a rejuvenated downtown area, and new places open all the time. The town spent 30 years and billions rejuvenating the down town area. They finished about ten years ago, and the town center is starting to age gracefully.
September/October are two of the most beautiful months in this area -- Franklin Lakes is about 35 miles from White Plains on the other side of the Hudson but with very similar climates. Lows of 35, highs of 75 or so. Can be rainy, and sometimes variable, but usually it's a delightful time of year.