Remove the vanilla ice cream from the freezer and let it sit at room temperature for about 3-5 minutes to soften slightly. This will make blending easier and create a smoother, creamier texture in your milkshake.
If using fresh peaches, peel and slice them into chunks, removing the pit completely. For the best flavor and texture, frozen peaches work exceptionally well as they're already chilled and blend smoothly without diluting the milkshake.
Add the softened vanilla ice cream to your blender first, followed by the frozen or fresh peaches. The ice cream should be scooped in generous portions to ensure a thick, restaurant-style consistency.
Pour in the cold whole milk and add the peach syrup or preserves along with the vanilla extract. The peach syrup intensifies the peachy flavor while the vanilla extract enhances the overall sweetness and depth.
Blend on medium speed for 15-20 seconds, then increase to high speed for another 20-30 seconds until completely smooth and creamy. You should see a uniform peachy-pink color with no visible chunks of fruit or ice cream remaining.
Check the consistency by stopping the blender and observing how the milkshake flows. It should be thick enough to coat the back of a spoon but still pourable. If too thick, add 1-2 tablespoons more milk and blend briefly; if too thin, add a small scoop of ice cream.
Pour the milkshake into a tall chilled glass, filling it nearly to the top. The milkshake should have a smooth, velvety appearance with a light peachy color reminiscent of the Chick-fil-A original.
Top with a generous swirl of whipped cream and place a maraschino cherry on top for the classic finishing touch. Serve immediately with a wide straw to enjoy the thick, creamy texture and sweet peach flavor at its peak freshness.