Shake with ice and allow the cubes to bruise the orange slices (or use a muddler before shaking). Strain into a tumbler filled with shaved ice, and decorate with berries of the season. Add straw.
This weekend when we went out grocery shopping, I purchased some blackberries in order to make the Sherry Cobbler off of the Anvil's 100 Drink list. On Sunday night, after finding the recipe in Jerry Thomas' Bartender's Guide, I opened up Imbibe! to see what David Wondrich had to say about this beverage. Wondrich described the Sherry Cobbler as "Nothing but sherry, sugar, a lot of ice, and a bit of fruit (a slice or two of orange muddled in with the ice and a few berries on top), and a straw." He also stated that Thomas more likely used a dry, pale sherry like a Fino or Amontillado, although sweeter, darker sherries could be used if you reduce the sugar (he recommends 2 tsp sugar for dry sherries and 1 tsp for sweeter ones, opposed to the 3 tsp in Thomas' recipe). With that historical note, I opted for our new bottle of Amontillado and set to work. Also new toy-wise for this drink was the handmade Lewis Bag we got at the BostonShaker store and wood mallet (purchased elsewhere) to make the crushed ice (ice geeking post forthcoming). The drink itself was very sherry with orange notes adding some complexity. Perhaps we would have gotten more oils from the rinds had I muddled them instead of bruising them with ice cubes during the shake (note: I garnished with virgin orange slices, and strained away what was left of the shaken ones). Even without the muddling, the juice and pulp was mostly freed from the rind. The Sherry Cobbler was a bit quizzical in that it looks and feels like a summery drink except that it uses an autumnal or wintery spirit.
The euphemisms are getting a bit stale, suffice to say: four people in Boston -- two of whom are much more prolific writers than the other two (including the originator of this blog, who has no excuse apart from laziness) -- who drink and tell.