“Looks like something out of Oliver Twist, doesn’t it?” Mark Brown remarked, the sentiment heightened by his English accent. “You may be the first to take photos up here,” he said, referring to the top room of the Dry House at the historic Buffalo Trace Distillery in Frankfort, Kentucky, where he has been president for 20 years. The Dickensian machine, the “Ro-Ball”, was literally chugging along, vigorously shaking a mash that is the by-product of distillation. Its purpose is to separate out the liquid from the solid, which will then be recycled and sold to cereal companies.

Elsewhere in the distillery, the mash is just beginning its life – starting with a mix of milled grains and limestone water that is first fermented to become beer and then distilled down into whiskey.

Buffalo Trace offers one of the best distillery tours in Kentucky, even though it is not technically part of the Bourbon Trail. Though not an actual route, the Bourbon Trail was created in 1999 by the Kentucky Distillers’ Association to promote bourbon tourism in Kentucky. It is a collection of six historic commercial distilleries scattered on either side of the Blue Grass Parkway: Wild Turkey, Woodford Reserve, Four Roses, Jim Beam, Heaven Hill and Maker’s Mark. Along the way are less travelled paths tempting visitors who are thirsty for Kentucky spirits and culture.

Bourbon was likely born in the 1770s when present-day Kentucky was first settled by Europeans. These settlers would have learned from the indigenous tribes how quickly and easily corn grew there, and then (since distillation was already a widespread practice) used any crop surpluses to make whiskey. When farmers later transported this unaged corn whiskey, or moonshine, across the Ohio River for commerce, the spirit would age in its oak barrel containers, becoming infused with dark colour and complex flavour. Since Bourbon County was one of Kentucky’s first counties, the resulting beverage came to be known as Bourbon whiskey. It was not until 1964, however, that the American government established bourbon as a distinctive product of the United States. A product of its history, today’s bourbon must be made from a mash of more than half corn, aged in an unused, charred oak barrel, and bottled at a minimum of 40% alcohol.

The story of bourbon’s past may enhance bourbon’s present as you start your journey along the Bourbon Trail with Barrel House Distilling Company, a micro-distillery that most tourists have never heard of. Located in historic Lexington, Barrel House has tours every day except Sunday, offering visitors the chance to see its whiskey, rum and vodka being made. The tour ends with a taste of the Devil John Moonshine, named after a local Civil War soldier and moonshiner. After all, moonshine (unaged whiskey), is as native to the region as bourbon.

While in Lexington, visit the ArtsPlace Performance Hall to take in a live bluegrass show – an equally authentic Kentucky experience. The weekly taping of Red Barn Radio is performed in front of a live audience and features some of the best bluegrass musicians from Kentucky and around the world.

Just outside of Lexington, four major distilleries entice bourbon lovers. Buffalo Trace dates back to 1857 when it became the country’s first steam-powered distillery. Its history is littered with such behemoths as EH Taylor, George T Stagg, Albert Blanton and Elmer T Lee. If you recognize the names, it is because there have been bourbons named after each one.

Today, the operation is huge, manufacturing bourbon for brands including Old Rip Van Winkle (our personal favourite), Eagle Rare and Blanton’s, in addition to its own eponymous brand. The hard hat tour takes visitors through the distilling process and may include a taste of whiskey straight off the still. This moonshine is a far cry from what your grandpa made in his basement during Prohibition. It is refined -- a bit spicy, yet clean and smooth with the sweetness of corn throughout. It is so good, in fact, that the distillery started bottling it upon the suggestion of a tour goer, despite reservations that Brown, the president, had about selling unaged whiskey. Buffalo Trace’s White Dog (white dog, white lightning, moonshine – they all mean unaged whiskey) is now one of the company’s top-selling products.

While on the tour, you will learn about the Experimental Collection, a series of whiskies made with non-traditional ingredients and/or processes. You may get lucky enough to taste one of these straight off the still as well. The newborn rice whiskey, for instance, is delicious -- light, fresh and reminiscent of sugarcane (which bodes well for its future aged release). The hard hat tour ends with a tasting of bourbons and bourbon cream liqueur.

To the south of Buffalo Trace in Versailles is Woodford Reserve, a small-batch boutique distillery and one of the stops on the official Bourbon Trail. The drive out to Woodford is picturesque, with rolling green hills and horse farms adorning the countryside. The distillery’s grounds are just as lovely, marked by old stone buildings and luscious greenery. The distillery tour details how Woodford’s bourbon is made, with a rye-heavy grain mixture and finishing by maturing in charred white oak barrels. The tour concludes with a taste of the bourbon and a bourbon ball (a truffle-like confections of chocolate and bourbon) to boot.

Enjoy a scenic drive from Versailles to Lawrenceburg, home to Wild Turkey, which was founded as the Ripy Family Distillery in 1869 by brothers John and James Ripy. It was bought in 1939 by the Austin, Nichols company, which still owns it today, under the Campari Group. According to the distillery, Wild Turkey got its name when executive Thomas McCarthy brought some company hooch along on a turkey hunting trip. When his hunting buddies later asked about the “wild turkey whiskey”, the name stuck. Despite its low price point, Wild Turkey makes some of the world’s best bourbon, highly regarded by professional whiskey tasters.

After touring the Wild Turkey facility, you may be lucky enough to taste Wild Turkey Rare Breed, a blend of six-year, eight-year and 12-year batches that is barrel proof (read: bottled without any addition of water) at 54.2% alcohol. It is robust and bold with a silky texture and the aroma of honey.

After a day of distillery hopping, head to Louisville for a nightcap. It is about an hour’s drive from any of the distilleries mentioned above, so you should probably stop off for a bite on the way. Opt for Ken-Tex Bar-B-Q in the town of Shelbyville, where Kentucky imports a bit of Texas for some hearty slow-cooked pork.

With the many tours and samples behind you, it is time to sit back, relax and sip a real glass of the good stuff. Dimly lit and laden in comfortable dark wood, Bourbons Bistro is an inviting den for tipple tasting in lively Louisville. Try the Van Winkle 12 Year, or, if they have it and you feel like spending a little extra, the Pappy Van Winkle 20 Year. Both very rare, the 12 Year is soft and buttery yet somehow refreshing and the Pappy 20 Year is deep and complex, washing over the palate with a bit of spiciness and traces of sherry and molasses.

If you have some time in Kentucky, continue your respite in Louisville by indulging in the local food and music. Start with a leisurely breakfast/brunch at Toast on Market, where you will have to wait for a table – but you will be glad you did. The cooks here treat eggs with the delicacy they deserve, poaching them into snugly formed clouds with runny, sun-coloured centres. Try the restaurant’s namesake, the Toast and Eggs, served on homemade brioche bread.

Then wander over to one of the three Bluegrass Brewing Company pubs in town. The St Matthews location is a brewpub that hosts live local music in its beer garden on Wednesdays and Thursdays. The company’s infamous bourbon barrel stout is a rich, roasty, velvety dark beer that has been aged in barrels from Four Roses Distillery. The menu includes the Hot Brown, an open-faced baked sandwich of smoked turkey, bacon, cheese and Mornay sauce invented in Louisville’s Brown Hotel in 1926, and the barbeque sandwich, a pulled-pork sandwich slathered in a sauce made with the company’s own Dark Star Porter.

More live music can be found at Zeppelin Café. There, local acts range from blues to bluegrass to folk and Americana.

From Louisville, head south for more distillery action. If you are ambitious you can hit three official Bourbon Trail outfits on your way to a lesser known gem, Corsair. Jim Beam is 30 minutes outside of Louisville, Heaven Hill and Maker’s Mark are farther south, and all three offer free tours and tastings.

Ninety minutes south of the Jim Beam Distillery, Corsair Artisan Distillery is making unique spirits on a very small scale. In bourbon country, this three-year-old operation amid a sea of old-timers is doing surprisingly well. “We don’t really feel the competition because we’re barely a blip on their radar,” said Clay Smith, the head distiller. The company caters to a niche market, focusing on making unique and experimental spirits from all-natural ingredients. “We have wanted to be known for our flavours, not necessarily for being the next bourbon maker,” he said. The distillery’s portfolio includes barrel aged gin, pumpkin spice moonshine, oatmeal stout whiskey and a more traditional (though fairly young) bourbon. The Triple Smoke is a tasty American single malt whiskey with a golden colour and a peaty butterscotch flavour. Tours and tastings are offered all day Friday and Saturday, but you can call ahead about stopping in on other days.