The Autumn Old Fashioned
A Recipe Development Journey
Part of an ongoing series exploring cocktails through iteration. Starting with an Old Fashioned because it’s familiar territory.
Following up on the iterative cocktail series I introduced earlier, I’m starting with an autumn-focused Old Fashioned. It’s late fall, apple cider is everywhere, and the template is familiar enough that I can recognize when something’s off. Cocktails are often seasonal in when you consume them—light and refreshing in summer, rich and warming in winter—so it makes sense to follow that pattern as I work through different builds. At least until I decide it doesn’t. For now, this seemed like the natural place to begin: testing how seasonal ingredients perform in a classic framework and documenting every step until I land on something worth drinking.
Version 1: The Thin One
The Build:
1.5 oz Jim Beam Sunshine
1 bar spoon dark brown sugar
Burnt orange bitters (Bluegrass Bitters)
Apple slice garnish
Muddled sugar with bourbon, built in glass
Why These Ingredients:
Jim Beam Sunshine was sitting on the bar cart, so that’s what I used. Bluegrass burnt orange bitters because I’d just interviewed them on a recent episode and they were already out. Brown sugar was part of the original concept—I wanted that deeper, molasses-forward flavor rather than simple syrup. Got apples specifically for this project because apple needed to be in here somehow. The construction was straightforward: muddle sugar with bourbon in the glass, add ice, garnish with apple. Classic Old Fashioned build, just swapping in fall ingredients.
What Happened:
This felt thin. The sugar dissolved fine, but the drink lacked weight. The burnt orange bitters added something, but not enough. Building in glass worked from a construction standpoint, just didn’t solve the fundamental problem.
The issue wasn’t just volume—though 1.5 oz didn’t help—it was also being too conservative on the bourbon’s flavor profile. Jim Beam Sunshine is approachable and wheated, which was the point, but it didn’t bring enough character to anchor the concept. I was worried about overwhelming the other ingredients when I should have been thinking about whether the spirit could actually carry them.
Key Takeaway: Too conservative on both volume and spirit selection. Needed more presence and more flavor to build on.
Version 2: Getting Closer
The Build:
2 oz Wilderness Trail 8 Year Wheated
2 oz apple cider
1 bar spoon muscovado dark brown sugar
Angostura bitters
Dried apple round garnish
Stirred in a shaker, dumped over ice
Why These Ingredients:
Wilderness Trail 8-year was one of the bottles from a blind tasting with friends earlier—figured I’d see how it performed here. Got muscovado sugar specifically for this iteration because it’s supposed to deliver more depth of flavor than regular brown sugar. Switched from burnt orange to Angostura because the orange just didn’t play right in the version I’m trying to make. Used dehydrated apple rounds because I needed to do something with the apples from the first attempt while I was waiting on the muscovado to arrive. Added apple cider at 2 oz to bring in actual fall character rather than relying on bitters alone.
What Changed:
More robust. Doubling the bourbon gave it the backbone it needed. The muscovado didn’t fully dissolve when I dumped it over ice, but honestly I think that’s fine—you get little pockets of molasses sweetness as you drink.
What Didn’t Work:
The Wilderness Trail brought too much oak to the cocktail. It worked well in the blind tasting context, but here the oak dominated everything else.
And with 2 oz of standard grocery store apple cider, the spice notes I’m chasing—cinnamon, nutmeg, allspice—aren’t showing up. The cider delivers apple, but not the fall character I’m after.
Which is frustrating, because if the cider isn’t doing that work, you start wondering if you should just use apple juice and add your own spices. But that’s a different project entirely, and I’m not interested in building spiced cider from scratch. If grocery store cider won’t deliver, that’s just the constraint I’m working with.
Key Takeaways:
Spirit volume is right at 2 oz
Age/oak matters—8-year brought character but the wrong kind
Grocery store cider isn’t delivering on spice
Angostura is better than orange but still not quite right
Construction method (stir and dump) is working
Muscovado was the right call
Version 3: Still Missing the Mark
The Build:
2 oz Milam & Greene’s Provision
2 oz apple cider
1 bar spoon muscovado dark brown sugar
Bittercube Bolivar bitters
Apple round on rim, dipped in caramel sauce
Why These Ingredients:
Milam & Greene’s Provision—instinct pick more than anything. Should bring less oak than the Wilderness Trail while still having enough character to hold up. Keeping the 2 oz spirit, 2 oz cider, and muscovado since those are working. Switching to Bolivar bitters to see if that plays better with apple. Caramel-dipped apple round on the rim instead of just dropping it in—might solve the spice problem through garnish rather than relying on the cider to do all that work.
What Happened:
The bitters were right. Bolivar played perfectly with the apple—finally something clicking into place.
But the whiskey is still wrong. Needs more spice. The Milam & Greene brought less oak than the Wilderness Trail, which was good, but it’s still not giving me what I need. The caramel garnish worked as intended—adds aromatics, looks good, gives you something to nibble—but the base of the drink isn’t there yet.
Here’s the real problem I’m wrestling with: the apple cider just isn’t that spiced. With grocery store cider, I’m getting apple flavor but none of those warm baking spices that should define fall. It could mean all the difference if you had access to a nice bespoke cider from a local orchard—something that actually tastes like cinnamon and nutmeg went into it. But I don’t, and I’m trying to make this work with what’s available.
I wonder if that’s the answer. If your cider is really good cider—properly spiced, robust—bourbon would work just fine. But if it’s weak grocery store cider, you need the spice profile of rye to get that kick. It’s not a proof problem, it’s a flavor problem. The spirit needs to compensate for what the cider isn’t bringing.
Key Takeaway: Bolivar bitters nailed it. Caramel apple garnish works. The cider limitation is real, and the spirit selection needs to account for that gap. This needs to split into two different approaches based on what ingredients you have access to.
The Split: Two Recipes for Different Realities
After all this testing, I realized I was fighting the wrong battle. The issue isn’t finding the perfect recipe—it’s that your ingredient quality dictates which direction you need to go. So here are two versions: one for when you’re working with standard grocery store cider, and one for when you have access to concentrated apple flavor.
Recipe 1: The Rye Route (For Grocery Store Cider)
When to use this: You’re working with standard apple cider that lacks robust spice character. The rye compensates by bringing the warm spice notes the cider won’t deliver.
The Build:
2 oz New Riff Bottled in Bond Rye
2 oz apple cider (standard grocery store)
1 bar spoon muscovado dark brown sugar
2 dashes Bittercube Bolivar bitters
Apple round garnish (caramel optional—see note below)
Stirred in shaker, dumped over ice
Why New Riff BiB Rye: 100 proof, bottled in bond, and it brings clean spice notes without overwhelming the apple. The rye’s spice profile fills in what weak cider can’t deliver. It’s widely available, making it accessible for most home bars.
Construction: Combine rye, cider, sugar, and bitters in a cocktail shaker with ice. Stir (don’t shake) for 30-40 seconds until well-chilled. Dump entire contents into a rocks glass. Garnish with apple round on the rim.
What This Tastes Like:
This version really nails the apple nose—you get that fresh apple character right up front without it being overly sweet. The Bolivar bitters are the “fancy” ingredient here, but if you don’t have them, orange bitters work fine if you like a little citrus with your cider. Oddly enough, this was the less sweet of the two final versions despite the caramel garnish. The rye keeps everything balanced and spice-forward rather than dessert-like.
Recipe 2: The Concentrate Route
When to use this: You’ve found apple cider concentrate (like Mountain Cider) that delivers concentrated apple and spice flavor. Mainly because you want to be precious about it. So maybe we do the same with the bourbon. Here it works beautifully because you’re getting the spice from the concentrate itself.
The Build:
2.5 oz Elijah Craig Toasted Barrel
0.5 oz Mountain Cider Apple Cider Concentrate (no sugar added)
1 bar spoon muscovado dark brown sugar
2 dashes Bittercube Bolivar bitters
Apple round garnish (caramel optional—see note below)
Stirred in shaker, dumped over ice
Why Elijah Craig Toasted Barrel: The toasted barrel finish brings caramel, cinnamon, and warm oak notes that complement the concentrated apple spice without competing with it. It’s a bourbon that already leans into fall flavors.
Why The Volume: With only 0.5 oz of concentrate, I bumped the bourbon to 2.5 oz to make sure there’s enough liquid in the glass. The concentrate delivers intense apple and spice character, so you don’t need much—but you still want a proper pour. This keeps the spirit as the star while the concentrated apple plays a supporting role.
Construction: Combine bourbon, concentrate, sugar, and bitters in a cocktail shaker with ice. Stir for 30-40 seconds until well-chilled. Dump entire contents into a rocks glass. Garnish with apple round on the rim.
What This Tastes Like:
This is definitely the sweeter of the two, leaning into dessert pour territory. Even though the apple cider concentrate has no added sugar, the natural sweetness from the Elijah Craig Toasted really comes through. The toasted barrel finish brings those warm, caramelized notes that make this feel more indulgent. If you want something to sip slowly by the fire after dinner, this is your version.
Why Two Recipes?
The ingredient quality dictates the path. Weak grocery store cider needs a spice-forward spirit (rye) to compensate. Concentrated apple flavor lets bourbon shine because the concentrate is already delivering those warm spices. It’s not about one being better—it’s about matching your approach to what’s actually in your liquor cabinet and on your grocery store shelf.
At the start I briefly considered rimming the glass with caramel sauce, cinnamon sugar, or some other spice mix. But then I remembered how much I actually despise rimmed glasses. It’s clumsy to consume, falls off about half the time, and usually hits you with so much of that flavor that you lose the cocktail for a minute. Don’t get me wrong—a classic well drink margarita with a salt rim is nostalgic, but it also sort of sucks to drink.
The caramel-dipped apple on the rim looks great for photos and video, but honestly it’s harder than it’s worth. I added it for the production shots, and it was a pain in the ass. A plain apple round on the rim works just as well for actual drinking—you still get the aromatic, and you can nibble it between sips without dealing with sticky caramel fingers.
Both versions use the same construction method, same bitters, same muscovado sugar. The only variables are spirit choice and cider form. Pick the version that matches your reality—and how sweet you want your autumn evening to be.
This is an ongoing series. Each version gets documented as I test it. Consider this the final article with both recipe paths.
What constraints are you working with in your builds? Drop a comment about what’s actually available to you.