July 18, 2025

From Stamps to Stories: My 972-Mile Bourbon Adventure On The Kentucky BourbonTrail

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The Kentucky Bourbon Trail journey sparked Tiny's bourbon passion and eventually led to the creation of the Scotchy Bourbon Boys podcast. What began as casual bourbon drinking with friends evolved into a full-blown obsession after completing the entire trail in 2019, covering 972 miles and 18 distillery locations.

• Originally started drinking bourbon while painting as an alternative to absinthe
• Discovered bourbon flavors through a whiskey desk calendar in 2018
• Saved $5,000 for a year to visit the Kentucky Bourbon Festival and complete the Bourbon Trail
• Completed all 18 locations of the 16 official distilleries in nine days
• Met bourbon legends like Fred Noe, Freddie Noe and Jimmy Russell
• Special experiences included dipping a Maker's Mark bottle and using a bung hammer at Jim Beam
• Received a commemorative glass upon completing the trail
• The Kentucky Bourbon Trail has expanded from 16 distilleries to 60 experiences across 27 counties
• Buffalo Trace and Barton's chose to leave the official trail but remain essential bourbon destinations

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How does a former absinthe-loving artist transform into a bourbon enthusiast? For me, it happened through an unforgettable 972-mile journey across Kentucky's rolling hills and distillery landscapes.

My bourbon adventure began unexpectedly when a desk calendar full of whiskey facts challenged my skepticism about flavor notes like "crème brûlée" and "cherry pie." This curiosity blossomed into a meticulously planned nine-day expedition through the Kentucky Bourbon Trail in September 2019. Armed with $5,000 I'd saved specifically for this pilgrimage, I set out to collect stamps from all 16 official distilleries.

The journey wasn't without challenges – from nursing a hangover after overindulging at the Kentucky Bourbon Festival gala to racing across time zones to reach Ozzy Tyler Distillery (now Green River) before closing. Each distillery offered unique moments: dipping my own bottle in Maker's Mark's signature red wax, using a bung hammer at Jim Beam, and sipping whiskey with legends like Fred and Freddie Noe.

What makes this story significant is how drastically the Trail has evolved since my completion. What began as seven distilleries in 1999 has exploded into 60 experiences across 27 Kentucky counties, generating $9 billion annually for the state's economy. The focus has shifted from stamp collection to personalized adventures, with distilleries offering specialized tours, cocktail classes, and dining experiences.

My commemorative completion glass – what I now call "the Eagle Scout Award badge for bourbon" – represents not just a tourist achievement but the beginning of a passion that spawned this very podcast and community. Whether you're planning your own bourbon pilgrimage or simply enjoying from afar, remember that good bourbon equals good times with good friends.

Have you completed any portion of the Kentucky Bourbon Trail? Share your experiences in the comments or tell us which distillery is at the top of your bucket list!