Many orchards sell pears and plums at the farm stand even when they do not open those rows for public picking. Some farms offer pick-your-own when the crop is strong. Either way, August and September are the months to pay attention.
Orchards and farms to watch
Lyman Orchards in Middlefield is one of Connecticut's big orchard names, with berries, sunflowers, mazes, farm-market energy, and a long fruit season. It is a natural place to watch for late-summer orchard fruit because the farm has the scale and visitor setup to carry people from berries into apples, pears, and fall activities.
Bishop's Orchards in Guilford is another Connecticut anchor for orchard shoppers. Farm-market strength matters with pears and plums because the fruit may be easier to find at the stand than in a public picking row.
Cider Hill Farm in Amesbury is useful for North Shore orchard trips that stretch across several crops. Its fruit calendar includes summer and fall favorites, and the farm store, bakery, and fields make it a strong late-summer stop.