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Slice tomatoes, either into ¼-inch thick slices, or halved and cut into 8-10 wedges.
Divide tomatoes among 3 pint jars, packing the tomatoes tightly in each jar.
Place a few slices of garlic and a few fronds of dill in each jar.
In a small saucepan, combine vinegar, water, salt, sugar, peppercorns, and red pepper flakes.
Bring to a simmer until sugar is completely dissolved.
Remove from heat and add bourbon.
Pour brine over pickles, filling jars to within ¼ inch of the top.
Make sure all of the tomatoes are fully submerged.
If they start to ‘float’, wedge a few more tomato pieces in there to keep them firmly packed.
Screw on jar lids and refrigerate for at least 3 days to allow pickles to fully pickle.
After that pickles will keep in the refrigerator for up to 2 weeks.