In a mixing glass, add 1 teaspoon of sugar, 1 teaspoon of water, and 5 dashes of Angostura Bitters. Muddle and stir until the sugar is dissolved.
Add ice to the mixing glass along with 2 ounces of Bourbon.
Stir until well chilled.
Add one large ice cube to a fresh rocks glass and strain the mixing glass ingredients into the glass.
Twist one peel of fresh orange over the glass and then run the twist along the inside of the rocks glass. Drop the orange twist into the glass.
Garnish with a Maraschino cherry in the bottom of the glass.