Switch Up the Fall Flavor With These Pear and Whisky Cocktails

While apples get all the attention come autumn, try your hand at one of these cocktail recipes that put pears front and center.

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How about them pears? While apples tend to steal the spotlight in the fall, pears are just as diverse. And since you can tease out pear notes in many whiskies, take advantage of the season’s fresh bounty and make these whisky cocktails. “The subtle caramel notes of whisky create a lovely dialogue with the subtle sweetness of pears,” says Ricardo Alvarado, bar manager of Mama Delia and Bordel in Chicago. “Together, these two make for a well-balanced cocktail that’s simple, evocative, and powerful all at the same time.”

3 Pear and Whisky Cocktails to Try Now

Nothing Comp-Pears to You: Poached pear is featured twice in this autumnal cocktail, both as a garnish and an essential ingredient.

Get the Recipe: Nothing Comp-Pears to You

The Fall of Whiskey: Cool cider and fresh pear balance out spicy rye in this cocktail, which is meant to capture the transition into Fall.

Get the Recipe: The Fall of Whiskey

The Affordable Pear Act: This riff on the Whiskey Sour uses baking spices and Asian pears to deliver fall flavors and a layer of complexity.

Get the Recipe: The Affordable Pear Act

How to Pick a Pear

Choosing the most appropriate pear and enjoying it at peak ripeness can make or break a recipe. For any variety, select a pear with no bruises or brown spots. Then check for ripeness by gently pressing near the stem—it should give a little. If not, let it further ripen on the countertop. Once a pear is perfectly ripe, keep it refrigerated.

Asian
Season: Sept.-Nov.
Flavor: Subtly sweet
Tip: Handle carefully; these bruise easily. They remain firm when ripe, like an apple.
Other uses: Green salads, slaws

Bartlett
Season: Aug.-Feb.
Flavor: Soft, sweetest of the pears
Tip: Buy green and let ripen on the countertop to a yellow-green.
Other uses: Baked goods, savory dishes, cheeseboards

Bosc
Season: Sept.-Apr.
Flavor: Honey sweet with hints of cinnamon and nutmeg
Tip: Bosc ripen before they’re soft, so they’ll be firm when ripe.
Other: uses Poaching, baking

D’Anjou
Season: Oct.-July
Flavor: Sweet with a hint of citrus
Tip: D’Anjou pears don’t change color when ripe; use the firmness test instead.
Other uses: Salads, baking

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The Fall of Whiskey [Cocktail Recipe]

Cool cider and fresh pear balance out spicy rye in this cocktail, which is meant to capture the transition into Fall.

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Created by Anthony Baker, a freelance cocktail professor, this refreshing drink hints of cooler weather ahead. The fresh pear and apple cider cool the heat of the rye whiskey with wonderful spice notes from the bitters.

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Nothing Com-Pears to You [Cocktail Recipe]

Poached pear is featured twice in this autumnal cocktail, both as a garnish and an essential ingredient.

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Elegant pear adds a velvety texture to this crimson cocktail, created by Summer-Jane Bell, partner at Hello Stranger Bar in Oakland, Calif.. “The aromatic spices and tannin from the wine play well with the cask notes in the whisky,” Bell adds.

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The Affordable Pear Act [Cocktail Recipe]

This riff on the Whiskey Sour uses baking spices and Asian pears to deliver fall flavors and a layer of complexity.

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This silky cocktail was created by Alec Pignotti, beverage manager at Recess in Chicago. It adds an extra layer of complexity to a Whisky Sour, with warm baking spices and Asian pears.

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4 Foolproof Whisky and Pumpkin Cocktails

Embrace fall flavors by whipping up one of these whisky and pumpkin cocktails, including seasonal takes on an Old Fashioned and a Hot Toddy.

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Pumpkin flavor instantly evokes memories of autumn: vibrant yellow and auburn-colored trees, a slight chill in the air, and the rustle of crisp leaves under your feet. And there are so many delicious ways to enjoy the fruit—yes, it’s a fruit—from pies to breads to soups and even whisky cocktails. “When pumpkin is cooked it releases natural baking spice flavors that wonderfully complement the barrel-aged notes in whisky,” says Billy Caruso, Chicago-based executive chef and beverage director at Rye Deli + Drink. “I like the viscosity and texture that pumpkin brings to a cocktail—it creates a more round and full-bodied mouthfeel.”

There are lots of possibilities for experimentation with pumpkin in a whisky drink. You can make pumpkin syrup, which typically consists of pumpkin puree, sugar, and water, and there are many ways to make it your own. You can use it to infuse whisky, which involves steeping pumpkin in the spirit, or you can simply add pureed pumpkin to your favorite whisky cocktail, which is how Caruso prefers to use it. “But I do have one tip if you’re going to puree the pumpkin yourself,” he says. “Always use a high-powered blender to get the pumpkin to a velvety-smooth texture. Otherwise it will break up when combined with other ingredients and make it look like your cocktail has sea monkeys in it—nobody wants that.”

4 Whisky and Pumpkin Cocktails to Try

Autumn Harvest: 2 oz. rye whiskey + 1½ tsp. pumpkin pie syrup + 3 dashes Angostura bitters
In a rocks glass stir rye, syrup, and bitters with ice for 15 seconds. Top with more ice and garnish with a star anise pod or cinnamon stick.
Created by Blaze Laroe of the since closed Chikatana in Chicago

Tangy Pumpkin Toddy: 1¼ oz. bourbon + 1¾ oz. Proof Pumpkin Spice syrup + ½ oz. Apologue Saffron liqueur + Hot water
Combine ingredients in a hot toddy glass and top with hot water. Garnish with powdered sugar-coated dehydrated pumpkin flesh pieces or Jelly Belly Pumpkins.
Created by Matt Shores from Daisies in Chicago

Pumpkin Old Fashioned: 1½ oz. bourbon + 2 Tbsp. pumpkin puree +  ½ oz. Grand Marnier + 1 oz. maple syrup + 2 dashes bitters
Combine bourbon, Grand Marnier, maple syrup, pumpkin puree, and bitters in a cocktail shaker filled with ice. Shake well and strain through a fine mesh strainer into a chilled Old Fashioned glass filled with fresh ice. Garnish with a rosemary sprig or orange peel.
From Boxer Hotel’s former Finch restaurant in Boston

Smashing Pumpkins: 2 oz. bourbon + 1 oz. pumpkin puree* + 1 oz. lemon juice + 1 oz. egg white
Dry shake bourbon, lemon juice, and egg white for 20 seconds. Add ice and pumpkin puree, shake for another 20 seconds. Double strain into an ice-filled rocks glass. Garnish with 2 dashes Angostura bitters.

*Peel, remove seeds, and dice a sweet pumpkin, roast at 300º until fork tender, about 45 minutes to an hour. While warm, add it to a blender along with water and puree until velvety smooth, adding more water if needed. Let it cool.
Created by Billy Caruso of Rye Deli + Drink in Chicago

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Roll the Dice With These Whisky-Themed Games

From barrel head checkers and bourbon playing cards, whisky is the theme for these at-home games.

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Sipping whisky with friends can be a fun pastime on its own, but why not make a night of it with whisky-themed board games? Bourbon-accented playing cards, a board battle that pits distiller versus distiller, whisky trivia, and a whisky barrel chess set—check out these game night choices.

Whiskey Business—$40
You and your friends are competing whisky distillers. Roll the dice to gather the ingredients and fill your barrels. The first to make four types of whisky wins.

Test your whisky knowledge with The Whiskey Game from Talking Tables.

Bicycle Bourbon Playing Cards—$7
Shuffle a deck of these vintage-looking playing cards with bourbon accents. Made in Kentucky.

The Whisky Game—$37
Correctly answer the whisky trivia questions to collect the different types of whisky to win.

Bourbon Barrel Chess Set—$5,495
The board is a laser-etched barrel head and the pieces are handcrafted from bourbon barrel staves.

Barrel Head Checker Set—$200
The checkers are cut from the staves of barrels; one set from the charred inside and the other from the outside. The playing board is a barrel head.

Sip and Play at These Board Game Bars

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How to Taste Bookish Notes in Whisky

From leather bound tomes to antique pages, learn how to pick up on notes otherwise found in your local library or book store.

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Many whisky lovers enjoy having their nose in a good book almost as much as a glass of whisky, and there are deeply evocative aromas common to both pleasures. The bouquet of some whiskies call to mind the antique scent of rows of books inside a library, in the cabinets of antiquarian book dealers, or along the miles of shelving stretching around enormous bookstores from Powell’s in Portland to the Strand in New York. Sales of print books rose during the pandemic as more people picked up a good read. (According to publishing industry tracker NPD Group, U.S. print book sales were up 8.2% in 2020 to 750 million books, while more than 200 million print books were sold in the UK last year—passing that mark for the first time since 2012, according to Nielsen BookScan.)

From a whisky nosing perspective, bookish aromas typically conjure up images of a gilt-edged tome bound in calfskin leather, perhaps with raised bands on the spine and archaic gold lettering, or a cloth-bound volume inside a slightly chipped dust jacket, its pages falling open to reveal gorgeous marbled endpapers, releasing the scents locked between the slightly tanned pages. Then again, other people like nothing better than cracking the spine on a freshly printed book or magazine and sniffing the modern chemicals in the paper, inks, and binding adhesives. So how can a whisky remind us of the smell of a good book?

The answer is right before you: paper in old books is made from wood pulp, which gradually decays over decades, releasing many of the same aromatic compounds found in oak casks. Scientists have even developed an odor wheel for describing and categorizing these old book smells, similar to whisky flavor wheels, deducing that the more prominent chemicals, such as vanillin, benzaldehyde, ethyl benzene, and the biscuit-like aroma of furfural come from the degradation of the wood compounds in the paper. Combined with the bindings and covering materials, they produce that curiously sweet mixture of vanilla, almond, dry leaves, and grassy notes, along with reassuring scents of polished antique bookcases, mustiness, and worn leather. To many, this attractive constellation is a signifier of a well-matured whisky.

Start your hunt with some of the less rambunctious single malt scotches and grain whiskies matured in second and third-fill bourbon barrels, move on to older single malt whiskies that rely on a contribution of refill sherry casks, and nose some bourbons and ryes to find those more mature leather, nut, and woody characteristics.

Whether your bookshelves are full of precious whiskies or pristine first editions, both have the power to transport you to other worlds.

Shelf Aware: These whiskies want to get into your good books

New Riff Backsetter Peated Backset Bottled in Bond Rye
Antiquarian Book: Old books, polished oak, sweet nuttiness

Kanosuke New Born
New Book: Peapod, bookbinding glue, Belgian chocolate

Deanston 12 year old
Leather Bound: Figs, polished calfskin covers, tobacco

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How to Pair Whisky and Snack Cakes

Learn how to pair Twinkies, Swiss Roles, and other store-bought snack cakes with bourbon, rye, single malt, and more.

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As rational human beings, we are all aware that some things we eat and drink are better for us than others. A glass of water is superior to a sugary cola after exercise, for instance, and an apple is nutritionally more sound than a cream-filled Twinkie or Swiss Roll.

So why do we so often reach for the less beneficial option? The answer, of course, is indulgence. That is why the snack cake endures as an American favorite, even many decades after America’s fitness obsession first took hold.

After fully exploring the category by wandering through the snack food aisles of various grocery stores, I settled on five principal snack cake categories: cream-filled vanilla cakes, cream-filled chocolate cakes, fruit pies, oversized cookie sandwiches, and various forms of glazed or frosted dough, from packaged donuts to honey buns. Then I got to work.

What became quickly apparent is the satisfying symmetry of the American snack cake partnering pretty perfectly with the iconic American spirit: bourbon. When pairing Twinkies and bourbon, however, target a whiskey with ample oak and vanilla richness and not too high a proof, since excess alcohol strength will overwhelm the cake-and-cream combination.

After trying several whisky styles with the chocolate and cream-filled Little Debbie Swiss Rolls, I concluded that scotch single malt is the way to go, either with abundant richness for a complementary pairing or impressive peatiness to develop a more contrasting relationship. I eventually settled on the peat, though it took me some time and quite a few Swiss Rolls to get there.

When it came to the Little Debbie Honey Bun, which various savants suggest is superior to the Hostess version, on a whim I tried Canadian Club Chronicles 42 year old, and found the combination to be quite superb. The bun’s sweet, cake-like character drew forward every last bit of spice in the spirit, creating a decadent cinnamon-bun experience that can be replicated with most moderately rye-forward Canadian whiskies.

Where hand-held or, as Drake’s Cakes puts it, “personal” fruit pies are concerned, the issue is more the pastry and glaze than the fruit filling, since the ratio of the former to the latter is much higher than in a regular fruit pie. I found that contrasting the sweet dough with something bold and spicy, like a straight rye, serves best. I settled in with a Wild Turkey rye poured over a couple of cubes of ice.

Lastly, while there might be a touch of romanticism involved in the idea that a whiskey from Ireland, a country so associated with oatmeal, would pair well with two oatmeal cookies sandwiched around cream, there is definitely a flavor connection between the Little Debbie Oatmeal Creme Pie and a sweet, rich, lemony whiskey like Hinch 5 year old Double Wood.

Doubling Down on Indulgence

Little Debbie Swiss Roll & Ardbeg Wee Beastie
A simple partnership that mixes smoke and chocolate to delightful effect, with a cream addition that complements both.

Little Debbie Honey Bun & Canadian Club Reserve
The bun coaxes out the spice of the spirit just as it did to the 42 year old, while the sweet oakiness of the whisky adds depth to the flavor of the bun.

Hostess Twinkie & Four Roses poured over an ice ball
With the ice taking the edge off the spicy spirit, the vanilla is allowed to emerge and enhance the flavor of the snack cake.

Video: How to Pair Whiskey and Snacks

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As With Bourbon, Kentucky Is a Thoroughbred Pacesetter

Just down the road from bourbon’s best-known distilleries lies Bluegrass Country, thoroughbred capital of the world.

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Kentucky, land of bourbon and horses, is a magical place. Within her borders lie hundreds of equine farms, making the Bluegrass State the world’s leader in thoroughbreds as well as bourbon. With more than a million acres of Kentucky land maintained for horses, it’s hard to miss the rolling pastures that are home to these remarkable creatures, that can be seen munching on grass and swatting pesky flies with their tails as you drive by.

Kentucky became home to thoroughbreds for many of the same reasons bourbon did: a four-season climate, fresh air, and limestone-filtered water. While providing a superb base ingredient for whiskey, the water also delivers a wallop of bone-building calcium to the pasture grass, along with its famous tinge of blue. Horses and bourbon were part of the picture even before Kentucky became a state in 1792. Commercial whiskey was distilled in Kentucky since the 1700s, and explorer Daniel Boone is credited with introducing a bill in Kentucky’s first Legislative Assembly aimed at “improving the breed of horses.”

Today’s Bluegrass country—a patchwork of pastureland stretching throughout central Kentucky—is home to more than 450 horse farms, many with storied pedigrees. Claiborne Farm in Paris, owned by the Hancock family for over a century, has been home to big-name horses like Secretariat and Seabiscuit. Nearby Runnymede Farm has raised thoroughbreds since the end of the Civil War. Stonestreet Farm is owned by the Jackson family, the renowned California vintners known for Kendall-Jackson and a host of other wines. Using his experience in finding and cultivating vineyard land in California, the family’s late patriarch, Jess Jackson, sought out just the right location for horses. Calumet Farm in Lexington, identified by its pristine white fencing and red-trimmed white barns, holds the record for the highest number of Kentucky Derby winners, at eight.

five horses being walked in a paddock

Founded in 1962 by Alice Chandler, Mill Ridge Farm raises and sells thoroughbred race horses. (Photo by John Stephen Hockensmith)

Raising A Winner

A horse doesn’t randomly grow up to race in the Kentucky Derby. Planning is often years in the making—with science, genetics, racing history, bone structure, and a little luck thrown in—before breeding takes place. The horse farms themselves are luxury accommodations with well-appointed barns (some with chandeliers and padded floors), manicured pastures, and impeccably maintained fencing.

Ashford Stud Farm in Versailles is part of Ireland-based Coolmore Stud, the world’s largest thoroughbred breeder, which is owned by Irish business magnate John Magnier. (Ashford’s land was originally part of a cattle farm owned by Col. Edmund H. Taylor Jr., founder of Old Taylor Distillery in nearby Frankfort, recently restored and rechristened as Castle & Key.) At Ashford, the horses lead a cushy life filled with sunshine and fresh air, and each has about a private acre of pasture. The farm employs more than 100 people—all focused on caring for its 16 stallions—either working directly with the horses or maintaining the farm’s 4,000 acres of lush grounds.

Enjoy Bourbon and Horses Together at Hermitage Farm

When a male horse’s racing career is over—usually around age three or four—he is put out to stud at farms like Ashford, where his job is to sire offspring to carry on his genes. Sometimes that job can go on for many years: An Ashford horse named Tale of the Cat, but often called the Elder Statesman, is 27 years old and still up to the task. In spring mating season, the stallion will breed with a mare—sometimes up to four times a day. The stud fee will depend on his racing history, pedigree, or both. One sought-after stallion is Uncle Mo, who is recognized more for his prized offspring than his racing career. When one of his colts, Nyquist, won the Kentucky Derby in 2016, Uncle Mo’s stud fee doubled to $150,000, and currently stands at $175,000. American Pharoah, who won racing’s Triple Crown (first-place finishes in the Kentucky Derby, Preakness, and Belmont Stakes) in 2015, commands a stud fee of $100,000. The price of entry is steep, but the returns can be sizable: Two years ago, one of American Pharoah’s offspring sold for $8.2 million.

A female horse is known as a filly until age 3 or 4 and is then called a broodmare during her fertile years, from age 3 to 22. The females also have plush accommodations and spend their days frolicking in the pastures with their fellow mares. Gainesway Farm in Lexington works with horses at all stages of their lives, but typically has 100 or so broodmares on its 1,500 acres. At breeding time—usually from February through the first week of July—they help mare owners matchmake with one of the farm’s seven studs. “We find out whether [the owners] want to breed, race, or sell, we research the pedigree, and we discuss a price range,” says Lakota Gibson, who handles sales and breeding at Gainesway. “Then we can find the right stallion.” A mare’s pregnancy, known as being “in foal,” lasts about 11 months, so she gives birth about once a year. As her due date approaches, the farm’s veterinarians monitor the mare around the clock.

man walks white horse down a path.

Tapit, one of seven stallions at Gainesway Farm, commands a stud fee of $185,000. (Photo by Equisport Photos)

Life for most of these horses begins at the nursery farms, which pamper the mother mare and raise the foal for its first year or year and a half of life—essentially serving as an equine preschool. Mill Ridge Farm in Lexington has been raising thoroughbreds for six generations. Alice Headley Chandler, who grew up on the land, established Mill Ridge in 1962 to focus on foals, and has raised many winners there. The farm covers about 600 acres and is sometimes home to more than 225 foals. The babies stay with their mothers until being weaned when they’re a few months old. The weanling (a foal that is no longer nursing) then gets moved to the fields with other adolescents. These teens, still getting used to their long legs and newfound freedom, play with their peers all day. Mill Ridge keeps a few older mares with them as a bit of adult supervision. The foals usually stay on the farm until the autumn of their yearling year, then head off to begin a life of training and racing.

When their careers are over, the horses need a place to live out their golden years. There are several retirement farms across the state, and among the best known is Old Friends Farm. This 236-acre retirement facility in Georgetown pampers thoroughbreds in their final years. Their mission is to provide a dignified retirement to the 128 horses that live there. Guests are welcome to walk the fence lines, led by a tour guide who can expound upon the achievements of its most famous residents. “We give the horses a sanctuary where they can live out their days,” says Old Friends board chair Cynthia Grisolia. “And we offer an opportunity to unite them with their fans.”

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Build Yourself a Barrel-Aged Home Bar

This collection of cognac, rum, tequila, gin, Cachaça, and wine will give you and your guests the full barrel-aged experience.

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Barrel aging is a crucial part of whisky making—it gives the spirit its color and adds a greater depth of flavor over time. Some styles even mandate the type of barrel or vessel used to age the whiskey. Bourbon, for example, is legally required to be placed in a new charred oak container meaning that once a barrel has been emptied, it can never be used to make bourbon again. So what happens to those barrels? They can be used to aged other types of whiskey like American single malt, or other types of spirits like gin, rum, or cognac.

Bourbon barrel aging can give these other spirits, and wine as well, an added dimension, as the oak likewise imparts color, but also flavors left behind from the whiskey. Taste that influence for yourself with these 10 bottles that offer something for whisky lovers looking to branch our into other spirits, and fans of those spirits looking to develop a taste for oak.

10 bourbon barrel-Aged spirits and wines to try now

Don Papa 10 year old Rum—43%, $70
This is Don Papa’s flagship rum—aged 7 years in bourbon barrels—but aged an additional 3 years in the same barrels that have been re-charred, resulting in a bolder spirit with cacao, roasted coffee beans, spice, tropical fruit, and toasted vanilla.

Martell Blue Swift Spirit Drink—40%, $46
With a base of VSOP cognac that’s finished for several months in bourbon barrels from Kentucky, Blue Swift has flavors of ginger, plum, and candied fruit followed by distinctive hints of vanilla and toasted oak.

Bluecoat Barrel Finished Gin—47%, $34
This fragrant and vibrant yet mellow gin is aged for a minimum of 12 months in charred new American oak barrels, which introduce caramel and vanilla without sacrificing the juniper and pepper notes.

Don Julio 1942 Tequila Añejo—40%, $140
Aged at least 2 1/2 years in bourbon barrels, this has roasted agave, vanilla, sun-ripened tropical fruits, with spiced undertones and a lingering touch of oak on the palate.

Espolòn Añejo Tequila—40%, $35
Espòlon Añejo is aged for a year—10 months in new American oak and 2 months in deeply charred Wild Turkey bourbon barrels. Vanilla and butterscotch complement the agave and earthy characteristics.

Novo Fogo Barrel-Aged Cachaça—40%, $35
This cachaça is aged 2 years in Kentucky bourbon barrels that have been taken apart, sanded, and re-toasted. Dominant flavors include banana bread, chocolate, cinnamon bark, coffee, and toasty black pepper.

Beringer Bros. Bourbon Barrel Aged Cabernet Sauvignon—14.2%, $20
Twenty percent of this cabernet is aged for 60 days in bourbon barrels, resulting in ripe tannins, toasted hazelnuts, blackberry, dark chocolate, vanilla, toffee, and black cherry preserves.

Ménage à Trois Bourbon Barrel Cabernet Sauvignon—14.8%, $15
Jammy blueberry and blackberry flavors, plus oak, vanilla, caramel and smoky spice characteristics are the result of aging 3 months in barrels that previously held Amador Whiskey Co. Double Barrel bourbon.

1000 Stories 2018 Zinfandel Batch #71—15.8%, $20
Aged in bourbon barrels for 3 months, this zinfandel’s subtle ripeness perfectly marries with the grilled herbs, sweet vanilla, and char flavors of the oak, with the kick of bourbon influence rounding out the finish.

Russian River Valley Pinot Noir Woodford Reserve Barrel Finish—15.2%, $50
After maturing 11 months in French oak, this pinot noir is aged 4 months in freshly emptied Woodford Reserve barrels. The palate is rich and juicy with soft tannins and lush red and black berries, with balanced acidity.

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