Monticello Wine Trail The wineries of the Monticello appellation fulfill a vision of Thomas Jefferson, whose aim was to produce exceptional quality wines like those he had tasted on his travels to Europe. There are 22 wineries in the region spread out over four separate wine trails. They all have their own grape plantings, although many also lease vineyards in order to increase their production. Most of the wineries and their Tasting Rooms are open to the public.