18 Fall Bourbon Cocktails You Need to Sip This Autumn Updated 06/2026

Cozy up, gorgeous. Your new favorite fall bourbon cocktails are waiting.

There is something about the first real chill of autumn that makes you want to reach for a glass of something warm, amber, and a little smoky. That something is bourbon, and fall is absolutely its season to shine. The spirit’s natural notes of vanilla, caramel, toasted oak, and baking spice harmonize with the flavors of the season so perfectly it almost feels like fate. Apple cider, maple syrup, pumpkin, cinnamon, pear, fig, cranberry, dark honey, and brown sugar all find their match in a good pour of bourbon.

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Whether you are planning a Halloween gathering, hosting a Friendsgiving dinner party, curling up by a bonfire, or simply treating yourself after a long week, this collection of fall bourbon cocktails has a recipe for every mood and every occasion. From elegant coupe glass sippers to oversized mug warmers, from five-minute shakers to slow-simmered party punches, these are the drinks that will define your autumn.

The Spirit Behind the Season: A Love Letter to Bourbon

Before we get to the recipes, let us take a moment to appreciate just how extraordinary bourbon is, because it deserves the recognition.

On May 4, 1964, the U.S. Congress declared bourbon whiskey a “distinctive product of the United States” by concurrent resolution, a designation that no other spirit in the world holds. That is not just a legal formality; it is a declaration that bourbon is woven into the identity of America itself.

Bourbon gets its name from Bourbon County in Kentucky, where it was first created, and the earliest known reference to bourbon whiskey comes from an advertisement in an 1821 issue of the Western Citizen newspaper. Its history stretches back even further, though, to the first settlers who brought European distilling traditions into Kentucky’s limestone-filtered landscape and started crafting something entirely new.

As of 2017, Kentucky had 1.9 million residents and 6.8 million barrels of bourbon aging in warehouses across the state, more than three barrels for every person in the state.

As of 2023, the Bourbon Spirits Market was valued at $8.4 billion, projected to grow at a compound annual growth rate of 7.2% through 2033. And it is not hard to see why. Bourbon is complex, soulful, deeply American, and endlessly versatile in a cocktail glass.

To legally be called bourbon, the spirit must be made from a grain mixture that is at least 51% corn, aged in new charred oak barrels, and produced in the United States. That charred oak barrel is where the magic happens, coaxing out those beloved vanilla and caramel tones that make fall cocktails so irresistibly comforting.

Your Fall Bourbon Cocktail Toolkit

Before you start shaking and stirring, stock your autumn bar with these seasonal essentials:

The Spirits: A mid-range, approachable bourbon works beautifully for most cocktails. Woodford Reserve, Bulleit, Buffalo Trace, Four Roses, and Maker’s Mark are all wonderful starting points. For sipping cocktails like Old Fashioneds, a single barrel or small-batch expression adds an extra layer of depth.

The Sweeteners: Pure maple syrup (Grade A dark for the most robust flavor), honey syrup (equal parts honey and warm water), brown sugar simple syrup, and demerara syrup are your go-to fall sweeteners.

The Aromatics: Fresh cinnamon sticks, whole cloves, star anise, cardamom pods, and fresh nutmeg. Always fresh where possible.

The Citrus: Fresh orange, lemon, and apple. Do not skip the fresh squeeze; it transforms a cocktail.

The Bitters: Angostura bitters are a classic. Orange bitters, aromatic bitters, and chocolate bitters are all wonderful supporting players in fall bourbon drinks.

The Garnishes: Dehydrated orange slices, cinnamon sticks, apple fans, rosemary sprigs, sugared cranberries, candied ginger, and maraschino cherries.

The Cocktails

Maple Old Fashioned

The vibe: This is autumn in a rocks glass. Rich amber bourbon swirled with real maple syrup and aromatic bitters, garnished with a wide strip of orange peel and a single large ice sphere. It is understated elegance, the kind of drink you sip slowly by candlelight.

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Ingredients:

• 2 oz bourbon
• 1/2 oz pure maple syrup (Grade A dark or amber)
• 2 dashes Angostura bitters
• 1 dash orange bitters
• 1 large ice sphere or cube
• Orange peel, for garnish

Instructions:

1. Add bourbon, maple syrup, and both bitters to a mixing glass filled with ice.
2. Stir slowly and deliberately for 30 to 45 seconds until well chilled and properly diluted.
3. Place your large ice sphere in a rocks glass.
4. Strain the cocktail over the ice.
5. Express the oils of a wide strip of orange peel over the surface of the drink, rub it around the rim, then drop it in or balance it on the ice.

Apple Cider Bourbon Smash

The vibe: Bright, crisp, and festive with a gorgeous deep gold hue. This cocktail looks like a golden autumn afternoon in a glass. The fresh lemon keeps it from being too sweet, the cider brings pure harvest energy, and the bourbon ties it all together with smoky warmth. Perfect for Thanksgiving tablescape or a fall porch hang.

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Ingredients:

• 2 oz bourbon
• 3 oz fresh apple cider (unfiltered, not juice)
• 3/4 oz fresh lemon juice
• 1/2 oz maple syrup
• 2 dashes orange bitters
• Ice
• Apple slice and cinnamon stick for garnish

Instructions:

1. Fill a cocktail shaker with ice.
2. Add bourbon, apple cider, lemon juice, maple syrup, and orange bitters.
3. Shake vigorously for 10 to 12 seconds.
4. Strain into a rocks glass filled with fresh ice.
5. Garnish with a thin apple slice tucked against the glass and a cinnamon stick.

Bourbon Hot Toddy

The vibe: The original comfort drink. A steaming mug of this gorgeous elixir is the color of golden honey, fragrant with clove and citrus, and warming from the first sip to the last. This is the drink for rainy autumn evenings, cozy fire pit nights, and any moment that calls for gentle, warming comfort.

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Ingredients:

• 2 oz bourbon
• 1 tbsp honey (or 3/4 oz honey syrup)
• 3/4 oz fresh lemon juice
• 6 oz hot water or hot chamomile/black tea
• 1 cinnamon stick
• 2 whole cloves
• Lemon wheel for garnish

Instructions:

1. Warm your mug by rinsing it with hot water, then discarding.
2. Add honey and lemon juice to the mug, then stir to combine.
3. Pour in the hot water or steeped tea.
4. Add the bourbon and give it a gentle stir.
5. Drop in the cinnamon stick and cloves.
6. Garnish with a lemon wheel on the rim and serve immediately.

Pumpkin Spice Old Fashioned

The vibe: You know that cozy, cinnamony, deeply spiced scent of a pumpkin candle? This cocktail IS that, in the best possible way. It glows a warm burnt orange, looks absolutely stunning in a heavy rocks glass, and tastes like a sophisticated autumn dessert. The pumpkin is subtle and earthy, not overwhelming, letting the bourbon stay front and center.

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Ingredients:

• 2 oz bourbon
• 1/2 oz pumpkin spice syrup (see below)
• 2 dashes Angostura bitters
• 1 dash chocolate bitters
• Large ice cube
• Cinnamon stick and orange peel, for garnish

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For the pumpkin spice syrup:

• 1 cup water
• 1 cup brown sugar
• 2 tbsp pumpkin puree
• 1/2 tsp cinnamon
• 1/4 tsp nutmeg
• 1/4 tsp ground cloves
• Pinch of ginger

Simmer all syrup ingredients over medium heat until sugar dissolves, about 5 minutes. Cool and strain through a fine mesh sieve. Keeps refrigerated for up to two weeks.

Instructions:

1. Combine bourbon, pumpkin spice syrup, and both bitters in a mixing glass with ice.
2. Stir for 30 seconds until chilled.
3. Strain over a large ice cube in a rocks glass.
4. Garnish with a cinnamon stick and curled orange peel.

Cranberry Bourbon Sour

The vibe: Tart, jewel-toned, and absolutely gorgeous. This cocktail is a showstopper at any gathering, with its deep ruby-red color and a frothy egg white foam crown. It is the perfect bridge between fall and the holiday season, sophisticated enough for a dinner party and fun enough for a Halloween cocktail hour.

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Ingredients:

• 2 oz bourbon
• 1 oz fresh cranberry juice (or 3/4 oz cranberry simple syrup)
• 3/4 oz fresh lemon juice
• 1/2 oz maple syrup
• 1 egg white (or 1 oz aquafaba for vegan version)
• Ice
• Sugared cranberries and a sprig of rosemary for garnish

Instructions:

1. Add all ingredients except ice to a shaker and dry shake (without ice) for 15 to 20 seconds vigorously to build the foam.
2. Add ice to the shaker and shake again for another 10 seconds.
3. Double strain through a fine mesh strainer into a chilled coupe glass.
4. Let the foam settle and rise beautifully.
5. Garnish with three sugared cranberries threaded on a cocktail pick and a small sprig of fresh rosemary.

Pear and Cinnamon Bourbon Cocktail

The vibe: Delicate, floral, and unmistakably autumnal. This cocktail has a blush-gold color with the gentle sweetness of ripe Bartlett pear playing against the bold warmth of bourbon. Garnished with a thin pear fan and a dusting of cinnamon sugar, it looks like it belongs in a lifestyle magazine spread.

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Ingredients:

• 2 oz bourbon
• 1 oz fresh pear juice (or 2 oz pear nectar)
• 1/2 oz cinnamon simple syrup (1:1 sugar and water simmered with 2 cinnamon sticks)
• 1/2 oz fresh lemon juice
• Ice
• Thinly sliced Bartlett pear fan and a cinnamon stick for garnish

Instructions:

1. Combine bourbon, pear juice, cinnamon syrup, and lemon juice in a shaker with ice.
2. Shake well for 10 to 12 seconds.
3. Strain into a coupe or stemmed cocktail glass.
4. Fan three thin slices of pear on the rim of the glass and add a cinnamon stick.

Bourbon Kentucky Mule

The vibe: Refreshing, gingery, and zingy with a gorgeous frothy top and a bright citrus aroma. Served in an icy copper mug, this fall take on the classic Moscow Mule swaps vodka for bourbon and adds a splash of apple cider. It glitters with ice and bubbles and is the ideal autumn patio cocktail on those warm early fall afternoons.

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Ingredients:

• 2 oz bourbon
• 3 oz ginger beer (good quality, spicy)
• 1 oz fresh apple cider
• 1/2 oz fresh lime juice
• Ice
• Candied ginger, lime wheel, and mint sprig for garnish

Instructions:

1. Fill a copper mule mug with crushed ice.
2. Pour in the bourbon and lime juice.
3. Add the apple cider.
4. Top with ginger beer and stir gently once.
5. Garnish with a lime wheel, a piece of candied ginger, and a small mint sprig.

Brown Sugar Cinnamon Old Fashioned

The vibe: Think warm pecan pie meets your favorite bourbon bar. This cocktail is deep mahogany in color with a caramel sweetness that feels almost dessert-like, yet stays sophisticated and bourbon-forward. It is the drink to make on a Friday night when you deserve something truly indulgent. The orange peel garnish brightens the whole thing beautifully.

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Ingredients:

• 2 oz bourbon
• 1/2 oz brown sugar cinnamon syrup (simmer 1 cup brown sugar, 1 cup water, and 2 cinnamon sticks for 5 minutes; cool and strain)
• 2 dashes Angostura bitters
• Large ice cube
• Orange peel twist for garnish

Instructions:

1. Stir bourbon, brown sugar cinnamon syrup, and bitters in a mixing glass with ice for 30 to 40 seconds.
2. Strain over a large single ice cube in a heavy rocks glass.
3. Hold the orange peel over the glass, squeeze to express the oils, twist, and lay it alongside the ice.

Hot Spiked Apple Cider

The vibe: This is the big-batch queen of fall entertaining. Imagine a deep copper pot on the stove filling your entire home with the scent of mulling spices and bourbon, drawing everyone into the kitchen. Served in heavy mugs with a cinnamon stick, this is the party drink that everyone talks about all winter long.

Ingredients (serves 8):

• 2 liters fresh apple cider
• 12 oz bourbon
• 4 cinnamon sticks
• 8 whole cloves
• 3 star anise
• 1 orange, sliced into wheels
• 2 tbsp honey or maple syrup
• Pinch of nutmeg

Instructions:

1. Pour the apple cider into a large pot over medium heat.
2. Add cinnamon sticks, cloves, star anise, orange slices, and sweetener.
3. Bring to a gentle simmer (do not boil) and let the spices infuse for 15 to 20 minutes.
4. Reduce heat to low and stir in the bourbon.
5. Ladle into mugs, making sure each mug gets a cinnamon stick and an orange wheel.
6. Dust with a pinch of freshly grated nutmeg.

Fig and Honey Bourbon Old Fashioned

The vibe: Rich, brooding, luxurious. This cocktail is an absolute stunner for holiday gatherings and dinner parties. It has a deep ruby-amber color from the fig syrup, a honeyed sweetness that lingers, and a garnish of a fresh or dried fig half that makes it look like something from a professional cocktail bar. It pairs beautifully with a cheese board.

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Ingredients:

• 2 oz bourbon
• 1/2 oz fig honey syrup (simmer 4 ripe or dried figs, halved, with 1 cup water, 1 cup honey, and a cinnamon stick for 10 minutes; strain and cool)
• 2 dashes Angostura bitters
• 1 dash walnut bitters (optional but wonderful)
• Large ice cube
• Dried or fresh fig half and a sprig of fresh thyme for garnish

Instructions:

1. Stir bourbon, fig honey syrup, and bitters in a mixing glass with ice for 30 seconds.
2. Strain over a large ice cube in a rocks glass.
3. Garnish with a halved fig and a small sprig of thyme tucked alongside.

Bourbon Manhattan (Fall Edition)

The vibe: Timeless, cinematic, and utterly elegant. Poured into a chilled coupe glass and garnished with a luxardo cherry dripping dark syrup, this cocktail looks like it belongs in a black-and-white film. The fall edition swaps rye for bourbon, and a touch of maple syrup softens and warms the classic to perfection.

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Ingredients:

• 2 oz bourbon
• 1 oz sweet vermouth
• 1/4 oz pure maple syrup
• 2 dashes Angostura bitters
• 1 dash orange bitters
• Ice for stirring
• Luxardo cherry and orange twist for garnish

Instructions:

1. Chill a coupe glass in the freezer for 5 minutes or fill with ice water.
2. Combine bourbon, sweet vermouth, maple syrup, and both bitters in a mixing glass filled with ice.
3. Stir for 30 to 45 seconds until very well chilled.
4. Discard ice from the coupe and strain the cocktail into the glass.
5. Garnish with a luxardo cherry on a pick and an expressed orange twist draped over the rim.

Gold Rush Cocktail

The vibe: Honey-gold in color, bright and citrusy on the nose, and warm with bourbon on the finish. The Gold Rush is a modern classic, born in New York in the early 2000s, and it feels particularly perfect in autumn when honey is at its most aromatic. Simple, stunning, and endlessly sippable.

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Ingredients:

• 2 oz bourbon
• 3/4 oz fresh lemon juice
• 3/4 oz honey syrup (2 parts honey, 1 part warm water, stirred to combine)
• Ice
• Lemon wheel and a sprig of fresh thyme for garnish

Instructions:

1. Add bourbon, lemon juice, and honey syrup to a shaker filled with ice.
2. Shake hard for 10 to 12 seconds.
3. Strain into a rocks glass over a large ice cube.
4. Garnish with a lemon wheel and a tiny sprig of thyme for a beautiful herbal aroma.

Bourbon Negroni (The Bournegroni)

The vibe: Bold, bitter, gorgeous. This is the cocktail for the woman who knows exactly what she likes and is unapologetically herself about it. The deep ruby-red color is stunning, the Campari’s bitterness is perfectly softened by the bourbon’s sweetness, and the large ice cube keeps it perfectly chilled without dilution. Garnish with a wide orange peel and prepare to be obsessed.

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Ingredients:

• 1 oz bourbon
• 1 oz Campari
• 1 oz sweet vermouth
• Large ice cube
• Wide orange peel for garnish

Instructions:

1. Combine all three ingredients in a mixing glass filled with ice.
2. Stir for 20 to 30 seconds until well chilled.
3. Place a large ice cube in a rocks glass and strain the cocktail over it.
4. Express a wide strip of orange peel over the surface, rub around the rim, and drape elegantly over the glass.

Blackberry Bourbon Smash

The vibe: Dark jewel tones of purple and black, muddled fruit glistening in the glass, and a frothy effervescent top from the club soda. This cocktail bridges late summer and early fall beautifully, celebrating the last of the season’s dark berries while nodding to the warming spice notes of autumn bourbon. It is a showpiece at any gathering.

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Ingredients:

• 2 oz bourbon
• 6 to 8 fresh or frozen blackberries
• 1/2 oz fresh lemon juice
• 1/2 oz simple syrup or maple syrup
• 4 fresh basil leaves
• Ice
• Club soda to top
• Blackberry and basil sprig for garnish

Instructions:

1. Place blackberries, basil leaves, lemon juice, and syrup in the bottom of a cocktail shaker.
2. Muddle firmly until the berries are fully crushed.
3. Add bourbon and a generous handful of ice.
4. Shake vigorously for 10 to 12 seconds.
5. Double strain into a rocks glass filled with fresh ice.
6. Top with a splash of club soda.
7. Garnish with a few whole blackberries on a pick and a fresh basil sprig.

Lion’s Tail

The vibe: A true vintage gem. Born in the 1930s, this forgotten classic deserves a serious revival. The combination of bourbon with allspice dram (an allspice liqueur) creates something that is both familiar and completely unique, deeply spiced and warming, with a citrus backbone from fresh lime. It is the cocktail equivalent of discovering a beautiful old record in a vintage shop. Served in a coupe, it is effortlessly sophisticated.

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Ingredients:

• 2 oz bourbon
• 1/2 oz allspice dram (pimento dram)
• 1/2 oz fresh lime juice
• 1/4 oz simple syrup
• 2 dashes Angostura bitters
• Ice for shaking
• Lime twist for garnish

Instructions:

1. Combine all ingredients in a shaker filled with ice.
2. Shake well for 10 to 12 seconds until very cold.
3. Strain into a chilled coupe glass.
4. Garnish with a twisted strip of lime peel draped over the rim.

Autumn Bourbon Sangria

The vibe: A big-batch beauty made for a crowd. This fall sangria is deep burgundy with flecks of golden pear and crimson apple, flecked with herbs and fragrant with cinnamon. It is the most stunning pitcher cocktail you will ever set on a holiday table. Make it the night before to let the flavors meld and deepen, and watch your guests swoon.

Ingredients (serves 6 to 8):

• 8 oz bourbon
• 1 bottle dry red wine (Merlot or Cabernet Sauvignon)
• 2 cups apple cider
• 2 tbsp maple syrup
• 1 pear, thinly sliced
• 1 apple, thinly sliced
• 1/2 cup fresh or frozen cranberries
• 2 cinnamon sticks
• 3 star anise
• 2 sprigs fresh rosemary

Instructions:

1. In a large pitcher, combine the wine, bourbon, apple cider, and maple syrup. Stir gently.
2. Add the sliced fruit, cranberries, cinnamon sticks, star anise, and rosemary.
3. Refrigerate for at least 4 hours, ideally overnight, to let the flavors marry.
4. Serve over ice in wine glasses, making sure each glass gets some of the gorgeous macerated fruit.
5. Garnish with a fresh rosemary sprig.

Spiced Bourbon Chai Latte

The vibe: Imagine your favorite chai latte had a glamorous older sister who has been to five continents and knows her way around a cocktail menu. Warm, steaming, frothy, and deeply spiced with cardamom, ginger, and cinnamon. This is the cozy mug cocktail for cold October evenings when you want something indulgent and warming but with a little extra magic.

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Ingredients:

• 2 oz bourbon
• 4 oz strong brewed chai tea (double strength)
• 2 oz oat milk or whole milk, frothed
• 1/2 oz maple syrup
• 1/4 tsp vanilla extract
• Pinch of ground cardamom
• Cinnamon stick and a dusting of cinnamon for garnish

Instructions:

1. Brew chai tea double-strong and let steep for 5 minutes.
2. Warm your mug by filling with hot water, then discard.
3. Add bourbon, maple syrup, and vanilla extract to the mug.
4. Pour in the hot chai tea and stir.
5. Froth the oat milk using a frother, milk steamer, or by warming in a jar and shaking vigorously.
6. Pour the frothed milk over the drink.
7. Dust generously with ground cinnamon and add a cinnamon stick.

Smoked Maple Bourbon Sour

The vibe: This is the cocktail that earns you applause at a dinner party. The egg white creates a cloud-like foam, the activated charcoal smoked salt rim frames the glass dramatically, and the maple syrup gives it a gorgeous amber warmth. A few drops of Angostura bitters on top of the foam, swirled into a design, make this look like something from a Michelin-starred cocktail bar.

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Ingredients:

• 2 oz bourbon
• 1 oz fresh lemon juice
• 3/4 oz pure maple syrup
• 1 egg white
• 2 dashes Angostura bitters (for the top)
• Ice
• Smoked sea salt or regular flaky salt for rim
• Orange peel for garnish

Instructions:

1. Rub half the rim of a coupe glass with a lemon wedge and dip into smoked sea salt.
2. Combine bourbon, lemon juice, maple syrup, and egg white in a shaker without ice.
3. Dry shake (no ice) vigorously for 20 seconds to build foam.
4. Add ice and shake again for 10 seconds.
5. Double strain into the prepared coupe glass.
6. Once the foam settles, add a few drops of Angostura bitters on top and use a cocktail pick to draw them into a swirl or heart pattern.
7. Express an orange peel over the foam and set it against the rim.

Tips for Elevating Your Fall Bourbon Cocktails

Make your own syrups. Homemade cinnamon syrup, maple syrup with a vanilla pod steeped in it, or a rosemary-honey syrup takes a cocktail from good to unforgettable. Most syrups take under 10 minutes to make and keep in the fridge for two weeks.

Use fresh citrus every single time. The difference between bottled lemon juice and a freshly squeezed lemon is staggering. Fresh juice is brighter, more vibrant, and gives your cocktail that clean, lively finish.

Invest in one beautiful ice mold. A single large ice sphere or cube melts more slowly than regular ice, keeping your drink colder longer without diluting the flavors. It also looks absolutely stunning in a glass.

Toast your spice garnishes. Running a cinnamon stick through a lighter flame for a few seconds before adding it to a hot toddy or mulled cider activates its oils and creates a beautiful, fragrant smoke that elevates the whole experience.

Batch your cocktails for parties. Any stirred cocktail can be made in a large batch in advance. Skip the ice (add it at serving time) and store in a sealed pitcher in the refrigerator for up to 24 hours.

Temperature matters. Cold cocktails should be served as cold as possible in chilled glasses. Hot cocktails should be served immediately in pre-warmed mugs. This one detail makes a dramatic difference.

The Perfect Bourbon Pairings for Autumn

Fall bourbon cocktails are even more wonderful when paired with the right foods. A Maple Old Fashioned is extraordinary alongside a cheese board with aged cheddar and honeycomb. The Cranberry Bourbon Sour loves a plate of dark chocolate or spiced pecans. Hot Spiked Apple Cider pairs beautifully with anything featuring sage, pork, or apple. The Bourbon Manhattan is made for a dinner of braised short ribs or mushroom risotto. And the Smoked Maple Bourbon Sour might just be the best dessert companion you have ever poured.

Your Autumn Bar, Your Rules

Fall bourbon cocktails are a celebration of the most beautiful season of the year. They are for golden afternoons and dark, starlit evenings. They are for long dinners that stretch past midnight and quiet moments on the porch wrapped in a blanket. They are for celebrating the harvest, honoring the chill in the air, and giving yourself permission to indulge in something truly, deeply lovely.

Bourbon has earned its place as America’s spirit, a 300-year-old tradition of craft, patience, and pride. This autumn, pour some respect into your glass, and stir in something seasonal and extraordinary.

The season is short. Sip slowly.

Pin this article for your fall entertaining plans, and tag your beautiful cocktails when you make them. We want to see your gorgeous autumn drinks!

Sources: https://chesbrewco.com
Category: Cocktails