The more I think about your proposed trip, the more it makes more sense to me for someone to do the out-and-back overnighter thing in the reverse order.

That is, start in Southwick and ride south to Farmington, CT for an overnight and then back north the next day. I don't know Southwick, MA, but google shows the closest hotel or motel is 10 miles from the end of the trail up there. I think it's more "motel" than "hotel."

On the Farmington side, there is a nice inn about 2 miles (easy ride) from the trail. Fine dining, pizza, a sandwich/dessert shop and frozen yogurt are all within walking distance of the inn. A longer walk (or short bike ride) away are other dining options like Asian and barbecue!