Bachelor Party Guide: Kentucky’s Bourbon Trail

First off, I’m not entertaining any conversations about a trip to Kentucky fitting inside my Midwest Bachelor party recs. Everything in this article is within 60 miles of the two stereotypical midwestern states. This is my website, these are my rules, and WERE DOING IT LIVE!

Second, spending time on the Bourbon Trail isn’t just a trip; it’s a pilgrimage. You’re not schlepping your buddy to some mid-major bar crawl—this is pre-civil war American history story told by your classy drunk uncle. But before you try telling your boys that Basil Hayden is actually a “pretty good pour” let’s get one thing straight: you need a plan for this trip.

The Location: This isn’t a “let’s wing it” situation. Where you stay and how you play will set the tone for your trip. Want a no-frills bourbon immersion? Book an air BnB in Frankfort—quiet, central, and small. You won't be doing a lot of interacting with strangers out in the middle of nowhere. If you’re a city person, Louisville, Lexington, and Cincy are your easiest bets. The distilleries are a short drive away and you’ll get the broader creature comforts that a big city can offer, like pro sports, traveling through major airports, and rowdier nightlife.

The Hook: Lets talk distilleries. You will probably want to visit 2-3 distilleries per day given that you’ll be on the trail for anywhere from 2 to 4 days. You should shoot to visit a different region each day and mix up the types of tours and distilleries. Just know that doing the “How Bourbon Is Made 101” tour at every stop is going to get old. Instead, focus on specialty tours, like top-shelf tastings and bartender-inspired cocktail menus. Distilleries will also offer novelties that are pretty cool too, like drinking straight from the barrel or taking home a custom laser-engraved bottle. There is a summary of the distilleries in each region at the end of the article but visiting the official website of the bourbon trail is a good idea. 

The Time Wasters: Bourbon on an empty stomach? Rookie mistake. Mammy’s Kitchen in Bardstown serves Southern comfort food that’ll keep you upright. Near Woodford Reserve, Wallace Station is a Bourbon Trail staple with killer sandwiches. For the final feast, The Rickhouse in Bardstown is the move—be a class act and cover the groom’s meal.

Tips for the Perfect Trip:

If you need a break from bourbon, check out the Kentucky Derby at Churchill Downs—even off-season, it’s worth a visit. Louisville basketball is iconic, and if you’re on the north end of the trial, Cincinnati’s pro teams are a way to mix in a light beer with all the brown liquor.

Last, I’m not your dad or anything, but - driving drunk isn’t cool. And you’re going to be drinking a lot. Much like a wine tour of Sonoma, the tastings are not close to one another, and you need to book transportation. Services like WhiskeyMe or Pegasus exist for this exact reason and usually start at $100 per person per day… its cheaper than a lawyer

Also, Pace yourself. 

The Golf:

• Sultans Run (~$100) – #4 Public Course in the country by GolfPass

• The Donald Ross @ French Lick (~$125) – #231 Couse in the country by Top100

• Yeah there’s also a Pete Dye course at French Lick, but golf is hard enough

• Topgolf Louisville - 301 Oxmoor Ln, Louisville, KY 40222

Not sold on the Bourbon Trail? Click HERE to view the entire catalog of BachTix Bachelor Party Guides!