Pop your rocks glass in the freezer for 5–10 minutes, or fill it with ice while you work on the rest of the drink.

If you’re using a large ice cube or sphere, take it out of the mold and have it ready — large ice keeps the drink from diluting too fast.

Pro tip: A quick chill for the glass makes the whole drink feel more polished. If you don’t have a freezer slot, just fill the glass with ice and dump it right before serving.

Pour ½ oz pure maple syrup into your mixing glass (or directly into the serving glass if you’re building the drink).

Add 2–3 dashes Angostura bitters on top of the maple.

Give those two a gentle stir or swirl to let the bitters thread through the maple syrup — you want them to start marrying before the bourbon arrives.

Pro tip: If your maple syrup is very thick (some grade B’s can be), warm it for 5–10 seconds in the microwave or thin it with a teaspoon of hot water so it mixes smoothly.

Measure 2 oz bourbon with your jigger and pour it into the mixing glass with the maple+bitters.

If you’re trying to keep this one of the easiest bourbon cocktails, building in the glass is fine — but for a cleaner presentation and cooler chill, I recommend using a mixing glass and straining.

Fill the mixing glass with enough ice to nearly top it.

Using a bar spoon, stir steadily: place the spoon against the inside wall, hold the mixing glass at a slight angle, and make smooth, controlled strokes.

Stir for about 20–30 seconds — you’re looking for the mix to be nicely chilled and just slightly diluted (that gentle dilution opens the flavors).

Pro tip: Slow, deliberate stirring (not shaking) gives you silkier texture and keeps the maple-bourbon balance intact. Think graceful circles, not frantic splashes.

If you used a mixing glass: dump the ice from your chilled rocks glass, add one large ice cube, and strain the chilled cocktail over it.

If you built it in the serving glass: add one large cube or a few medium cubes and give a gentle stir to marry everything.

Take a wide strip of orange peel (about 1.5–2 inches). Hold it with the outer peel facing down over the glass.

Give it a firm twist to spray the oils across the surface of the drink, then rub the peel along the rim and drop it in.

Add a brandied cherry on a pick if you’re feeling fancy.

Pro tip: Don’t skip expressing the orange — those oils cut through the richness and brighten each sip.

Take one small sip. If it tastes a hair too sweet, add one dash more bitters or next time cut the maple to ⅓ oz.

If it’s too stiff for your mood, add a splash more maple or a tiny bit of water to open it up. Adjust in small increments — a little goes a long way.

Settle in and savor: this is meant to be sipped slowly, the kind of maple bourbon cocktail that rewards quiet conversation.