Served over crushed ice and with a straw.
In its day, the cobbler was THE drink. Its simple construction of spirit, sugar, and fruit, mixed thoroughly with ice, and served with straws was fairly groundbreaking. In the 1830’s, when the cobbler appears to have first come onto the scene, not only was ice in this fashion a fairly new occurrence, but so were drinking straws. The modern paper straw was first patented in 1888, and prior to that the straws served with drinks would be just that, straw. Usually the dried hollow stalk of rye, cut to length is what would be served with the Cobbler, perhaps the first drink to call for its use. The name “Cobbler” is believed to reference the small chunks of ice which fill the drink like a “cobble” stones.
For an example, see: