Welcome back to The Bourbon Road! This week, hosts Jim Shannon and Todd Ritter are diving deep into the history and flavor of one of America's most iconic whiskey brands. We are keeping a long-overdue promise to our listeners by doing a side-by-side comparison of the highly sought-after extended age Old Overholt rye whiskeys.

If you are a whiskey history buff, you know that Old Overholt holds the title for the longest continuously maintained whiskey brand in the United States, dating all the way back to 1810. Founded by Abraham Overholt in West Overton, Pennsylvania, it began as a classic Monongahela-style rye. We discuss its fascinating early history, back when frontiersmen transported the whiskey in casks on flatboats down the Monongahela and Ohio Rivers, stopping at the Falls of the Ohio before continuing to St. Louis and New Orleans. In those days, patrons would fill up ceramic jugs straight from the barrel! After being acquired by Jim Beam in 1987, the brand was moved to Kentucky, where corn was introduced to the mash bill to create a "Kentucky-ized" profile that many consider a "bourbon drinker's rye." Now, the brand is returning to its premium roots by offering higher-aged, cask-strength releases that harken back to the 1940s when you could get a 121-proof Old Overholt right from the cask.

In this episode, Jim and Todd line up the 10-Year, 11-Year, and 12-Year Old Overholt Cask Strength Rye whiskeys to see how each year of extra aging and varying proofs impact the flavor profile. As always, they analyze the nose, palate, and finish of each expression before combining them for a final "Blendageddon" experiment.

On the Tasting Mat:

• Old Overholt 10-Year Cask Strength Rye: Released in 2023, this 121-proof powerhouse was sourced entirely from Warehouse V—an "escalator" warehouse in Clermont. At an MSRP of $100, the guys are instantly struck by its dark cherry and oaky warehouse nose. On the palate, it delivers a massive impact with a cherry-honey combo, a deep richness that isn't overly sweet, and a light breath of rye spice that lacks any polarizing dill or mint notes. It boasts a remarkably long finish that leaves a lasting impression and a solid Kentucky hug.

• Old Overholt 11-Year Cask Strength Rye: Released in late 2024, this batch drops the proof down to 107.4 and shifts the aging to warehouses M, J, F, and 5. Also retailing around $100, this pour offers a much lighter, cleaner nose with hints of peanut brittle and subtle oak. The palate takes a sharp turn into "candy rye" territory, delivering rich notes of maple syrup, brown sugar, and sweet crystalized sugar sticks. While the finish isn't quite as long as the 10-year, it provides a beautifully balanced, sweet, and approachable experience that hides its proof effortlessly.

• Old Overholt 12-Year Cask Strength Rye: The senior member of the lineup steps the proof back up to 117. Also aged in warehouses M, J, F, and 5, this expression brings a completely different profile and a retail price of around $110. Boasting a rich mahogany color with thick legs on the glass, the nose is bursting with berry jam—think raspberries and strawberries—with a touch of dried cranberry tartness. The palate is a luxurious "berries and cream" experience, offering a velvety, salivating mouthfeel. It balances the sweetness with a leathery, slightly white-pepper spicy finish that lingers just as long as the 10-year.

• The "Blendageddon" Old Overholt 10/11/12-Year Custom Blend: To close out the tasting, Todd mixes equal parts of all three expressions, resulting in a custom blend sitting right around 114.4 proof. The guys discover that the bold 10-year and 12-year expressions dominate the softer 11-year, creating a complex pour that leads with the 12-year's berry notes and finishes with the 10-year's spicy, leathery bite.

Tune in to hear Jim and Todd debate the merits of each vintage, discuss the fascinating history of the brand, and ultimately reveal their personal rankings of these three exceptional ryes. Which age statement will reign supreme? Grab a glass, pour your favorite rye, and join us on The Bourbon Road to find out!