Hi, I also live in MD. (Hagerstown) We definately get some cold days here and I would definately suggest buying a few sweaters or even Pjs. (fleece ones keep them so warm) If your baby is going to go outside to potty then I would definately get something. I never had luck keeping the boots on. Mine hate them. My two yorkies use the little box with a pee pad in it instead of litter. However, since it started to get cold they always have something on them even if they don't go out. My pekingese goes outside to potty and always has a sweater on. Little dogs get colds so easily so I think any type of clothing is better then none. Good Luck to you and Congrats!! on the new little one