Old Fashioned

2 oz. rye or bourbon
1 tsp. water
1 sugar cube
2 dashes Fee Bros. old fashion aromatic bitters, or Angostura

In a rocks glass, muddle the bitters with the sugar and water. Add a few large ice cubes and the whiskey, stir to combine. Garnish with a broad peel of orange, making sure to twist it over the top of the drink, and a cherry.

This is a "whiskey cocktail made the old fashioned way". The ingredients of this drink represent the original cocktail, but it first appeared in print in 1880. There should never be a pulpy mess of fruit at the bottom of an old fashioned. The orange peel, twisted over the drink, should release enough oils to give a slight orange flavor. Caster or superfine sugar could replace the sugar cube and probably dissolve better, or you could use simple syrup.

Applejack Cobbler

2 oz. applejack
1/4 oz. simple syrup
2 dashes peach bitters
2 strawberries
4 blackberries

Muddle the the berries, syrup, and bitters in a mixing glass, then add the applejack. Shake with ice and strain into a footed or highball glass filled with crushed ice. Garnish with blackberries and quartered strawberries. Serve with a spoon and a straw, or a spoon-straw.

The cobbler was the most popular drink of it's time, the king of which was the Sherry Cobbler (sherry, sugar, ice, orange slices, muddled and garnished with berries). This drink was first mentioned in print in 1809, but most early references come from the 1840's when it really became popular. A few decades later it had moved past just wines to include spirits as a base, and was still going strong. In the 1888 edition of Harry Johnson's Bartender's Manual, he noted that the Sherry Cobbler is "without a doubt the most popular beverage in the country, with ladies as well as with gentlemen. It is a very refreshing drink for old and young." Along with the Julep, this drink helped popularize the use of ice in your drink (and was possibly the first to be shaken with ice), and the straw was almost unheard of. Still a great summer drink with endless variations.

Trilby

1/2 oz. Scotch
1/2 oz. Parfait Amour
1/2 oz. Sweet vermouth
2 dashes absinthe
2 dashes orange bitters

Stir over cracked ice and strain into a cocktail glass.

The Trilby has been around since at least 1895, and has taken many different forms (great post on it here). These days a Trilby would be made as a Manhattan with orange bitters, a delicious drink but not as interesting as this version. This recipe most closely resembles Harry Craddock's Trilby cocktail no. 2 (1930), however I first came across it in the great literary work that is Easy To Make Maidens & Cocktails: A Mixing, Swingers Bar Guide (1965). The measurements listed make for a pretty small drink, but with the equal proportions it's easily adjusted. I use a blended scotch for this one, such as Johnnie Black.