There's a reason that bourbon is historically produced in Kentucky (even though legally it can come from anywhere in the US): the limestone filtered water and locally-grown grains just plain taste better, and the fact that the region has, for most of history, made most of America's bourbon, means that the people there have a deep passion for it, and they also have old-school, time-tested recipes, too. Whether you're a bourbon snob, or you just like drinking, the Kentucky Bourbon Trail is a must-visit.
After that, check out the Maker's Mark Distillery. It's worth it to buy a bottle here, because you get to dip the top in the iconic red wax yourself! Also, take some time to enjoy the bucolic setting of this distillery.
Once you get to Shepherdsville, visit the Jim Beam Distillery. Since it's the largest maker of Kentucky bourbon, you'll get a different view: that of a larger-scale operation. As one of the largest sellers of bourbon in the world, their tour seems to reflect that in having one of the more interactive tours. The tour guides are very knowledgable and encourage questions.
The final distillery is back up near Louisville: The Bulleit Frontier Whiskey Experience. The original distillery opened on Derby Day in the 1930s, and it recently reopened for tours.
Starting off in Louisville, visit the Evan Williams Bourbon Experience. They give a really thorough background on the drink and Louisville's history with it (and yes, it ends with a tasting). Seeing as this is the only "bourbon tour" in Louisville proper, it's worth the stop. The samples were pretty small, but it's straight bourbon, so you're probably gonna feel pretty good afterward. Grab a bottle or some bourbon balls in the gift shop afterwards!
Next, work off that bourbon tasting with a quick visit to the Louisville Slugger Museum, to see where professional baseball bats are made. It's a pretty cool museum and factory tour, and will definitely make you appreciate old hitters and their bats. Plus, everyone who visits gets a mini souvenir Louisville Slugger for themselves!
Next up is the Buffalo Trace Distillery. It's not a part of the Kentucky Distillers Association's official Bourbon Trail, but they are, however, open for tours and tastings. They have a few iconic bourbon brands that are produced here: Buffalo Trace, Blanton's (with the little horse on top of the round bottle), and Eagle Rare. If you've got a sweet tooth, definitely also try the bourbon cream (it's perfect if you're still not sold on straight bourbon) and bourbon brittle.
Then make a quick stop at folk legend Daniel Boone's Gravesite for a great photo op (especially if you happen to have one of those coontail hats).
Then head to The Woodford Reserve Distillery. It's a National Historic Landmark, but it's also gorgeously maintained, and set in a dreamlike corner of the Bourbon Trail. Here, you'll enjoy rolling hills as far as the eye can see. The tour takes you through the entire distilling process from start to finish, so you'll get to see the still, the warehouse, and the bottling process. Also, they have a cafe if you're looking for a place to grab food while on the trail.
Next, hit up Wild Turkey Distillery, which has been crafting Kentucky bourbon since 1869. They offer both tours and tastings individually, so if you'd rather skip seeing the still and warehouse, you can just sample their wares-- try the sweet and spicy Wild Turkey Honey Stinger!
Right down the road is the Four Roses Distillery. They have 10 different varieties of bourbon, and a really unusual, Spanish-style building that houses the distillery. Plus, if you save your ticket from the distillery tour, you can tour their warehouse operation, located in Cox's Creek, for free!
Even the most enthusiastic bourbon-lover can't just barrel through and sample bourbon at 9 places all in a rush. You won't be able to fully appreciate every sip if you don't take a break to clear your mind and your palate! Luckily, there's lots to do (and eat) in Kentucky while traveling from distillery to distillery (or rather, from sample of bourbon to sample of bourbon). Eating is important, of course, and luckily, there are tons of local restaurants where you can get a great meal to soak up some of the liquor. Plan to spend at least 2-3 days traveling along the Bourbon Trail, and stop off at some of the many charming Kentucky towns along the route.
The best time of year for a road trip down the Bourbon Trail: Summer is high season along the trail, so you'll have more crowds to contend with, and hotels will be slightly more expensive. A beautiful time of year, however, is mid-September to late-October. You'll avoid most crowds, enjoy off-season hotel prices, and the scenery along Kentucky's rural roads is unsurpassed in autumn. From beautiful fall foliage, to pumpkin patches and farm cider, this is the best time to experience the Bourbon Trail.