Though bourbon can be made anywhere in the country, its production is synonymous with one place and one place only—Kentucky. Scattered across the Bluegrass State are more than 15 bourbon distilleries, from large-scale producers like Wild Turkey to the craft spirit makers of Corsair Artisan Distillery. Sadly, it's impossible to reach every one in a single outing. However, a pocket of producers near Lexington are close enough to each other that it's feasible to hit them all in a daylong road trip, bouncing from one tasting room to the next along the dirt-covered country roads of the Kentucky Bourbon Trail. Even better news: Designated drivers abound. For instance, Mint Julep Tours provides a two-day bus package for $198, while R&R Limousine will cart you around for packages starting at $270. Every tour includes a tasting, which should be more than enough evidence as to why no other place on earth will ever rival Kentucky when it comes to bourbon.
8:23 A.M. Kick off the morning with a pastry and coffee from the Midway School Bakery, just northwest of Lexington. Here, everything is local—from the Ruth Hunt Candies from nearby Mount Sterling to the Kentucky Nut Corporation's freshly grown pecans. Your best bet, however, is the Weisenberger cake doughnut with cinnamon sugar. And since there's drinking to be done, grab a second option to go—preferably the blueberry cake doughnut with powdered sugar icing.
8:55 A.M. Though not an official member of the Historic Bourbon Trail, the first stop on the trip is the Buffalo Trace Distillery*. Christened a National Historic Landmark in 2013, Buffalo Trace is described by the National Parks Service as "a rare, intact example of a distillery operating before, during and after Prohibition." (No joke—the site has been distilling, storing and shipping bourbon whiskey for more than 200 years.) Take the traditional Trace Tour through aging warehouses and into Blanton's Bottling Hall, where its flagship Buffalo Trace Kentucky Straight Bourbon Whiskey is bottled, labeled and packaged for distribution. Because it's the first tasting of the day, see if you can snag a sample of the Eagle Rare Single Barrel, which has a fruity, herbal scent and notes of cocoa and candied almonds.
10:38 A.M. Though distillers have been making whiskey on the property since the 18th century, Woodford Reserve, the Official Bourbon of the Kentucky Derby, wasn't actually introduced to the market until 1996. (The property was originally occupied by Oscar Pepper Distillery.) Seven dollars will buy you one of the best tours on the trail, which includes a long look at the towering copper pot stills responsible for Woodford's distinctive triple-distillation process—the only copper pot still and triple-distillation process used to handcraft bourbon today. After the tasting and a complimentary bourbon ball, Kentucky's chocolate-covered version of the rum ball, wander over to the gift shop. Once inside, purchase a bottle of Woodford's latest, Woodford Reserve Double Oaked, a twice-barreled bourbon that ages for a year longer than its flagship whiskey in a freshly charred barrel, intensifying its smoky flavor.
12:14 P.M. Wallace Station, near Woodford Reserve, is the perfect spot to take a break from drinking and re-commence eating. Its menu is standard deli fare—burgers made with Kentucky-raised beef, sandwiches and soups. Order a Southern classic, Browning's Country Ham & Pimento Cheese sandwich on rye with a side of slaw. Avoid the congested seating area of the main restaurant in favor of a picnic table on the expansive back porch.
12:56 P.M. Roll down country roads past pastures, farms and ranches plucked straight from a Grant Wood painting on the way to the campus of Wild Turkey, the most modernized distillery on the trail. For $5, a short shuttle ride brings drinkers from the visitors' center to the giant production facility, where a three-story-tall turkey painting peers down from the side of the building. Inside, the tour moves past vats of bubbling whiskey in different stages of the fermentation process. Be sure to look through the 8-foot windows into the lab where Master Distiller Jimmy Russell tastes each batch for consistency. The tour ends back in the visitor centers' tasting room, which provides a panoramic view of the Kentucky River. Try Russell's Reserve Small Batch Single Barrel; it's unfiltered bourbon that explodes with an intense caramel and vanilla flavor.
2:47 P.M. Venture 9 miles down US-127 to the Four Roses Distillery in Lawrenceburg, which features the most visually stunning architecture of contemporary bourbon makers. Built in 1910, the distillery has a distinct Spanish Mission-style facade, which looks both beautiful and bizarre in Colonial-style Kentucky. This complimentary tour is a bit shorter than the others—mostly because, unlike Woodford Reserve and Buffalo Trace, there's no barrelhouse to walk through since Four Roses doesn't age on site. That's because Four Roses uses single-story rack warehouses in order to minimize temperature variation between barrels and provide more consistent flavor, which takes up a lot of real estate. As such, Four Roses ships its barrels down to a large, rural property in southern Kentucky. (Other distilleries build very tall barrelhouses in order to conserve space.) But don't fret. There are still giant cypress fermenters and piping hot stills to wander around, and most importantly, good bourbon to taste—namely, the Small Batch, a spicy, fruity blend that's super smooth for easy drinking. Maybe too easy.
3:51 P.M. Conclude the pilgrimage back in Lexington proper, at Lexington Brewing and Distilling Company's Town Branch Distillery. Because the facility is equal parts brewery and distillery, the $7 tour covers both beer and bourbon (as well as twice the tastings). On the beer side, have a Kentucky Bourbon Barrel Ale. It's aged for six weeks in fresh bourbon barrels to give it a delicious, brown-sugar-like flavor. On the distillery side, you can actually dip your finger into the fermenting whiskey to sample the grainy, yellow foam. While the bourbon is excellent, don't miss a taster of Bluegrass Sundown, a bourbon-infused coffee liqueur that makes Kahlua taste like Folgers.
5:39 P.M. Chef Ouita Winter's prix fixe menu at the Holly Hill Inn changes not just by season, month or week, but every 48-72 hours. For instance, throughout the first three months of 2014, she's been taking guests on a culinary world tour, aptly named "Around the World in 80 Days." From London to Indonesia to the Horn of Africa, the cuisine takes on a new region bi-weekly. Her recent China menu consisted of Dong Po Pork Belly roasted in ginger, hot-and-sour cabbage, scallions and sugar. And for dessert she offered a Crank & Boom Green Tea Ice Cream Sundae with fresh raspberries, white chocolate cream, crushed pistachios and crystallized ginger butter squares.
8:42 P.M. That's enough bourbon for one day—or week depending on your normal bourbon intake. Sleep it off at the Gratz Park Inn in Lexington's Historic District. The rooms are decorated with 19th century antique reproductions, mahogany furniture and local artwork. It might be early, but tomorrow is another full day. This time, however, it will be filled with the Bluegrass State's other passion: gambling on horses.
*Ed. Note: This post was modified to clarify that Buffalo Trace is not an official member of the Historic Bourbon Trail.
Tyler Moss is the Online Editor for Family Tree Magazine. His writing has also appeared in DRAFT, Outside, mental_floss and Salon.com.
Photo courtesy of the Kentucky Distillers' Association