The 10 Most Expensive Pappy & Old Rip Van Winkle Bourbons


While Pappy Van Winkle bourbons are far more expensive and sought after than those of its sister brands (Old Rip Van Winkle, Van Winkle Family Reserve and Van Winkle Special Reserve), with a starting price of about $800, none of these whiskeys can be called cheap.

And that’s just the standard expressions. Some of the less common and rarer expressions are even more costly. Here are the ten most expensive Pappy and Old Rip Van Winkle bourbons.

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1. Pappy Van Winkle’s Family Reserve 23 Year – $8,950

A bottle of Pappy Van Winkle's Family Reserve 23 Year

As mentioned, all the bourbons made by the Old Rip Van Winkle distillery are expensive, even the standard expressions, and the following table shows you just how expensive even the standard expressions are.

Price
Old Rip Van Winkle 10 Year$799.99 – $1,599.99
Van Winkle Special Reserve 12 Year$899.99 – $1,599.99
Pappy Van Winkle’s Family Reserve 15 Year$1,499 – $4,499.99
Pappy Van Winkle’s Family Reserve 20 Year‎$4,200 – $7,600
Pappy Van Winkle’s Family Reserve 23 Year$5,000 – $8,950
Van Winkle Family Reserve Rye 13 Year$1,999.99 – $3,999.99

As you can see, not only are these whiskeys expensive, they also have a price range. That’s because the distillery only releases around 84,000 bottles a year, and because they’re highly sought after, they’re usually sold before they reach the shelves, and then resold for a higher price.

The Pappy Van Winkle expressions are, as mentioned, more expensive than the others but the most expensive of the standard expressions at between $5,000 – $8,950 is the Pappy Van Winkle’s Family Reserve 23 Year.

2. Old Rip Van Winkle Bottled in 1934 – $24,699.99

A bottle of Old Rip Van Winkle Bottled in 1934

This is a rare, prohibition-era, 18 year old, Old Rip Van Winkle bourbon. It was distilled a few years before the start of prohibition and bottled in bond afterwards, in 1934. This bottle was found in the safe of a retired pharmacist, as this whiskey was sold for medicinal purposes at the time.

It comes in a pint-sized bottle with a cardboard box and a government tax strip. This piece of history will cost you $24,699.99.

3. Pappy Van Winkle’s Family Reserve 1984 – $27,556

A bottle of Pappy Van Winkle Family Reserve 1984

As mentioned above, Pappy Van Winkle’s Family Reserve 23 Year is the oldest and most expensive of the standard expressions, but the 1984 Pappy Van Winkle’s Family Reserve 23 Year is even more expensive – $27,556.62 instead of between $5,000 – $8,950.

This is for two reasons. First because it’s an exclusive 2007 single barrel bottling for the Kentucky Barrel Society and second because it’s made with whiskey that was distilled at Stitzel-Weller – the distillery built in 1935 by Julian ‘Pappy’ Van Winkle Sr which was sold by the Van Winkle family in 1972 and then later closed in 1992. Any remaining stock from the original distillery is revered, including this expression.

To the tune of tens of thousands of dollars.

4. Old Rip Van Winkle Bicentennial – $29,999

A decanter of Old Rip Van Winkle Bay Colony Bicentennial

During the mid-1970s there was a series of celebrations that paid tribute to historical events leading up to the creation of the United States of America. This Old Rip Van Winkle seven year old bourbon was made in 1975 and marks the Bay Colony bicentennial.

The whiskey itself is believed to be from the original Stitzel-Weller distillery, and it comes in a white porcelain decanter that has pictures celebrating the bicentennial.

This is a limited edition, some of which were sold for less than $1,000 a few years ago. Those still for sale now cost much, much more – $29,999.

5. Van Winkle Double Vertical 2020 & 2021 – $32,500

Van Winkle Double Vertical 2020 & 2021

As mentioned, the Old Rip Van Winkle distillery releases their expressions yearly and in extremely limited quantities. The Van Winkle Double Vertical is the 2020 and 2121 release.

The 12 bottles in the collection are:

  • 2 bottles of Old Rip Van Winkle 10 Year
  • 2 bottles of Van Winkle Special Reserve 12 Year
  • 2 bottles of Van Winkle Family Reserve Rye 13 Year
  • 2 bottles of Pappy Van Winkle’s Family Reserve 15 Year
  • 2 bottles of Pappy Van Winkle’s Family Reserve 20 Year in a red velvet bag
  • 2 bottles of Pappy Van Winkle’s Family Reserve 23 Year in a black velvet bag

To buy one of each expression (six bottles) at the maximum prices mentioned above would cost you $28,250, so two of each expression for $32,500, while expensive, is a relative bargain.

6. Van Winkle 16 Year Pot Stilled – $34,995

A bottle of Van Winkle 16 Year Pot Stilled

The Van Winkle Pot Stilled Selection whiskeys are extremely rare. There’s a 16 year old and a 17 year old expression, both of which were bottled in the early 1990s. They were originally created for the Japanese market but eventually they became available in the United States.

Some bottles of the 16 year old were sold for $12,999 and some bottles of the 17 year old were sold for $23,999. Now the remaining 16 year old Van Winkle Pot Stilled Selection whiskeys will cost you $34,995.

7. Van Winkle Handmade 16 Year – $39,999

A bottle of Van Winkle Handmade 16 Year

The Van Winkle Handmade bourbons are extremely rare whiskeys. They were both distilled in 1974 but the 16 year old expression was bottled in 1990 and the 17 year old expression was bottled in 1991.

Although they were made before the Stitzel-Weller distillery was closed in 1992, it’s thought that the whiskeys were distilled at the Boone distillery in Petersburg, Kentucky – the same place as the early Pappy Van Winkle’s Family Reserve 20 Year expressions.

These whiskeys are the only Van Winkle bottles with red wax – a short-lived idea that had to be abandoned when they were told to cease and desist by Maker’s Mark who hold the red wax trademark.

Bottles of Van Winkle Handmade 16 Year are sold for $19,000, $29,999, and $39,999.

8. Old Rip Van Winkle Family Selection – $44,999.97

Old Rip Van Winkle Family Selection 23 Years Decanter Set

The Old Rip Van Winkle Family Selection is a 23 year old whiskey produced from a small batch of 1986 vintage Stitzel-Weller barrels chosen by Julian III and his son, Preston Van Winkle, which was bottled in 2009 at 114 proof or 57%ABV. Not only is this bourbon from original stocks, it’s also the first time that the 23 year old was made at a strength other than the series standard of 95.6 proof or 47.8%ABV.

The whiskey comes in a hand graved crystal decanter and solid wood, leather-lined box that also contains two Glencairn glasses and a Certificate of Authenticity signed by the company President, Julian P. Van Winkle III.

Only 1,200 sets were released, the most expensive of which costs $44,999.97.

9. Van Winkle Corti Brothers Special Reserve – $49,995

A bottle of Van Winkle Corti Brothers Special Reserve

The Corti Brothers – a family grocer located in Sacramento, California, would search for bourbons they liked and order their own bottlings. They contracted their first exclusive Van Winkle Special Reserve bottling in 1987, and this bottle from 1994 is one of only a handful that followed.

Two bourbons were bottled at that time – a 19 year old whiskey from the Fall distillation of 1975 and a 20 year old whiskey from the Spring distillation of 1974.

In the 1990s these bottles sold for between $20 and $40 each – which is next to nothing in Van Winkle bourbon terms. However, fast forward a few decades and a bottle of the 19 year old will cost you $24,776 and a bottle of the 20 year old will cost you $49,995.

10. Old Rip Van Winkle 25 Year Old – $64,999.99

A bottle of Old Rip Van Winkle 25 Year Old

This whiskey was distilled in 1989 and bottled in 2015. It was uniquely aged as it comes from only eleven barrels that were stored on the lower levels of a metal clad warehouse at the Stitzel-Weller distillery until 2002, when they were moved to the lower floors of the brick warehouses at the Buffalo Trace distillery, where they continued to age for another 12 years.

The bottle the whiskey comes in is actually a handmade glass decanter from Glencairn Crystal Studio with two stoppers – one of silver and one of glass, and the number of the bottle is engraved on each decanter. The decanter comes in a wooden box made from the staves of the above-mentioned eleven barrels that the whiskey was matured in. They’re signed by Julian Van Winkle.

Only 710 of these bottles were made, and their original retail price was a mere $1,800. As expected, none of these extremely rare and limited bottles made it to the shelves, and the price has increased dramatically to between $49,995 – $64,999.99.

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Josh Mitchell

I'm Josh Mitchell. I love whiskey and am working on increasing my whiskey tasting abilities and my collection.

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