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Mix the sugar and cherries in a medium bowl or large mason jar, mashing the cherries as you mix.
Cover with a towel and let sit at room temperature for 24 hours.
Mix in the vinegar and vanilla. Place in the fridge for 12-24 more hours to let the flavors develop. Then, taste and add more vinegar to your preference.
Strain just before serving - I find that the drink develops better flavor if the cherries stay in the jar. Serve 1-2 ounces of shrub as a mocktail topped with club soda and a garnish of fresh mint.
Add the sugar, water, and cherries to a small saucepan. Bring to a simmer and let cook, stirring occasionally for 5 minutes.
Remove from the heat and stir in the vinegar. Let cool for at least 10-15 minutes, then strain through a fine mesh strainer. Taste and add more vinegar to your preference.
Serve 1-2 ounces of shrub as a mocktail topped with club soda and a garnish of fresh mint.