A Road Trip Along the Kentucky Bourbon Trail








The Kentucky Bourbon Trail was one of my most favorite road trips. Driving on small roads through acres of rolling green hills, horse farms, and charming towns is wonderful to experience. This is a trip that you can take solo or with a group of friends or family, as it has something for everyone.


The Kentucky Bourbon Trail.

In 1999 the Kentucky Distillers’ Association formed the Kentucky Bourbon Trail tour to give visitors a firsthand look at the art and science of crafting bourbon and to educate the consumer about its history and tradition. According to the Association, approximately 1.2 million people visited the distilleries in 2017, an increase from the prior year.

In the 1700s local farmers and frontiersmen found that converting corn and grains to whiskey was easier that getting crops to market over the narrow trails and steep mountains in the area. The name bourbon came from one of Kentucky’s original counties, Bourbon, which was established in 1785 when Kentucky was still part of Virginia.

Farmers shipped their whiskey in oak barrels, stamped from Bourbon County, down the Ohio and Mississippi Rivers to New Orleans. The long trip aged the whiskey, with the oak wood providing a distinct mellow flavor and amber color. Bourbon is still made in Kentucky and across the US and is more popular than ever.

Today the Kentucky Bourbon Trail includes 10 distilleries where you can tour and taste. You can get a Bourbon Trail passport and collect stamps at all 10 and even get a free t-shirt. The urban bourbon experiences like Evan Williams and Jim Beam in Louisville are okay, but I really prefer visiting the actual distilleries rather than downtown storefront tasting rooms. There is also a Kentucky Bourbon Trail Craft Tour that includes small and new distilleries that are well-worth the visit.

I was able to visit a number of these distilleries on my most recent trip. I loved learning about their history; seeing the old rickhouses, or aging warehouses; and tasting some of the best bourbons.

Frankfort, Kentucky

Don’t miss Buffalo Trace (113 Great Buffalo Trace) on your visit to the area. It is the oldest continually operating distillery in the United States, making bourbon for over 200 years. During Prohibition, the distillery was even permitted to remain operational in order to make whiskey for “medicinal purposes.” It sits on 440 acres and has many historic rickhouses onsite. It is currently a National Historic Landmark.

They offer a number of tours. I enjoyed the Trace Tour, which gives you a historic overview and information on the stages of the bourbon-making process. You get to see the aging warehouses, bottling line, and taste some of their 16 different bourbons. I really enjoyed the Eagle Rare Single Barrel Bourbon and the Buffalo Trace Bourbon. Other brands in their Antique Collection included the famed Pappy Van Winkle, Old Charter, W.I. Weller, and Blanton’s Single Barrel. Tours leave every hour, but I highly suggest that you book your tour online before you go. There are five different tours, each followed by a free tasting.


Buffalo Trace.


Glasses at the ready.

Before or after your visit to Buffalo Trace, make sure to drive through Frankfort. It has a charming historic downtown with some local stores, cafes, and antique shops.

Not far from Frankfort is Midway, Kentucky. Located in the middle of Kentucky’s Bluegrass horse country, it has a charming main street that is well-worth the visit. It was the first town in Kentucky established by a railroad, along an east-west railroad line in the 1830s. It has a number of stores, cafes, and local businesses. With three restaurants in town, Chef Ouita Michel has helped put Midway on the map.

Don’t miss historic inn turned restaurant, Holly Hill Inn, featuring locally sourced food. It’s the perfect spot for Sunday brunch. They feature a three course menu with several options.

Just south of downtown is The Midway Bakery (510 South Winter Street). Stop in for a snack or a coffee while you explore. They create cookies, pies, scones, and more from scratch using locally sourced ingredients and traditional recipes.

A little further south, at 3854 Old Frankfort Pike, is the charming Wallace Station that is open for breakfast, lunch, or dinner. It has both indoor and outdoor patio seating and is located in a former grocery store that was built in the early 1900s. The strawberry pie was definitely worth the drive!

Lawrenceburg, Kentucky

The Wild Turkey Visitors Center, Lawrenceburg (1417 Versailles Road) is a stunning visitor center overlooking the Kentucky River Valley. Here you can enjoy a tasting of their bourbons and rye whiskeys. Tours are available, as well.

The Four Roses Distillery visitor center is located at 1224 Bonds Mill Road in Lawrenceville. Here you can take distillery tours year-round. Founded in 1888, they are the only distillery that has used the same grain source for more than 50 years. They produce three bourbons: the Single Barrel Bourbon, the Small Batch Bourbon, and the Four Roses Yellow.

The distillery, built in 1910, is listed on the National Register of Historic Places. The Single Barrel and the Small Batch Bourbon are both excellent, the latter named America’s Best Kentucky Bourbon in 2016.

Versailles, Kentucky

I highly recommend taking a tour of Woodford Reserve (7855 McCracken Pike). It is one of Kentucky’s oldest and smallest distilleries, built on the site where Elijah Pepper began crafting whiskey in 1812. It is a National Historic Landmark, and it is known as the “Homeplace of Bourbon.”  It was here that Master Distiller James Crow perfected his whiskey-making methods, which have become common practice, including the implementation of sour mash into fermentation.


Woodford Reserve.

They also feature a number of special dinners and tastings throughout the year. Chef Ouita Michel has Glenn’s Creek Cafe at the visitor’s center, which is a great spot for lunch.

The tour was one of my favorites—you can see the historic buildings and iconic copper pot stills. I thought the Double Oaked Bourbon was really outstanding.


Aged barrels at Woodford Reserve.

Lexington, Kentucky

I thoroughly enjoyed my three-night stay in Lexington. My top recommendations include:


Races are held twice a year, in April and October, at this internationally famous racecourse and an auction house for the Kentucky thoroughbred industry. Tours are available all year long. When there are no races, you can go to the track between 9 and 10 am to watch the horses during their morning workout on the track. I did this and loved the flexibility to watch and walk around the grounds without the crowds.



Blue Door Smokehouse

This is a fun spot for BBQ and sides in a casual spot east of downtown Lexington. It was my first stop as I drove into town. I had a great brisket sandwich with collard greens and potato salad. They feature brisket, pulled pork, pulled chicken, sliced turkey, and smoked sausage. They also feature a number of salads, ribs, sides and desserts. I had a great brisket sandwich with collard greens and potato salad. I highly recommend it. 226 Walton Ave.  

Barrel House Distilling Company

Located within the James E. Pepper Distillery campus and occupying the original barreling house dating back to 1780 is the Barrel House Distilling Company. Next door is the Elkhorn Tavern, their bar and tasting room where you can grab a cocktail and listen to live music. They make a bourbon, vodka, rum and moonshine.

Middle Fork Kitchen Bar

Located in the same complex, Middle Fork has great food in a contemporary/industrial setting in the old distillery building. They feature a number of small plates, pastas, meats, and seafood. I enjoyed my dinner with my friends.

Alltech Lexington Brewery and Distilling Company

This is a newer brewing operation in Lexington that was first known for its Kentucky Bourbon Ale, which is aged up to six weeks in used bourbon barrels. They also make a number of IPAs, porters, and stouts. This led the way for them in establishing the Town Branch Distillery in 2012, where they make the Town Branch Bourbon, a rye whiskey, a gin, and a malt whiskey. The whiskeys are excellent. Make sure to sign up for a tour and tasting, as it is great experience. 401 Cross Street.

Lockbox at the 21c Hotel

I had a really excellent meal at the restaurant of the 21c Hotel downtown at 167 West Main Street. Since the hotel has an emphasis on contemporary art, make sure to visit one of their current exhibitions.

James Beard-nominated chef, Ouita Michel, in addition to her three listed above in Midway, has three places in Lexington, two of which I tried. These included:

Honeywood Restaurant

At 110 Summit at Fritz Farm, this is an upscale residential, retail, and restaurant development. I tried the recently opened Honeywood Restaurant with local friends. Recommended by the Holly Hill Inn, I tried and loved the vegetarian beetloaf, a take on meatloaf made with shredded beets, carrots, sunflower seeds, sesame seeds, and cheddar topped with a tomato-onion sauce and served with mixed root vegetable puree and a small salad.

Smithtown Seafood

Adjacent to West Sixth Brewing at 501 West 6th Street, this is her casual restaurant, emphasizing local foods and old-fashioned Kentucky recipes. I enjoyed the shrimp and grits. With no seating in the restaurant, you can opt for the large tasting room of West Sixth Brewing. Here you can try one of their ales, porters, IPAs, or wheat beer along with seasonal and limited release offerings.

James E. Pepper Distillery

At 1200 Manchester Street, the former James E. Pepper Distillery (1780 to 1855) has been transformed into a large complex featuring restaurants, bars, a microbrewery, and a distillery. The James Pepper Distillery is remodeling part of the original building and will reopen in the original facility. It was one of my favorite places that I visited when I was in town.


Eight Pole Inn, Lexington.

I also highly recommend staying at the Eighth Pole Inn, a really stunning B&B inn in the middle of the horse country in Lexington close to Keeneland. The rooms are lovely, as is the living room, dining room for breakfast, and outdoor patio. I am so glad I stayed here as it was an easy drive downtown as well as to Frankfort, Midway, and some of the best bourbon distilleries. Besides, I loved looking out the window of my room and seeing horses in the fields surrounding the inn. 3463 Rosalie Road.

Loretto, Kentucky

The Maker’s Mark Distillery is the world’s oldest operating Bourbon whiskey distillery on its original site at 3340 Burks Spring Road in Loretto. Make sure to book a tour through the site with stops at the original owner’s house, the Quart House, Still House, and Bottling House. You can enjoy a tasting of their whiskeys.

They make the Maker’s Mark Private Select, Cask Strength, and Maker’s 46. From Wednesday to Sunday, you also might enjoy having lunch before your tour onsite at Star Hill Provisions, featuring locally sourced ingredients. It is located in a renovated distiller’s house.


Dale Chihuly installation at Maker’s Mark.

Lovers of the work of the glass artist Dale Chihuly will love seeing his piece that he created in 2014 in the ceiling of one of the rickhouses. It is a 40-feet long and 6-feet wide canopy of colored glass, which he called “the Spirit of the Maker.” “What pleases me most about the Spirit of the Maker is how it contrasts with the space it inhabits,” Chihuly says. “Surrounded by stacks of dusty, wooden barrels and hovering above a floor of unfinished wood planks, its hues of red, blue, green, and amber create a warm and ethereal environment.”

Bardstown, Kentucky

Located in central Kentucky south of Louisville, Bardstown is a charming historic city—Kentucky’s second oldest—first settled in 1780. It is on the National Historic Register. The historic district of 26 blocks has 279 properties. The town has shops, restaurants, small inns, and bed and breakfasts, along with a number of bourbon distilleries nearby. Fodor’s named it one of America’s Best Small Towns.

I recommend that you spend at least one night to at the historic Bourbon Manor B&B so that you are able to explore the town and the surrounding area. Stop by the visitor center and grab a map to do a walking tour of the historic buildings.

Located on the south side of Bardstown, is Bourbon Heritage Center Heaven Hill Distillery. You can tour and taste the bourbons of the Heaven Hill Distillery and visit the exhibitions on the history and production of bourbon. Tastings include the golden amber Henry McKenna Single Barrel, the smooth and full-bodied William Heaven Hill 5th Edition, the 25-year-old whiskey, the Very Special Old Fitzgerald wheated bourbon, and the spicy Pikesville Rye Whiskey. They also make the Elijah Craig and Evan Williams brands. I learned that by adding three drops of water, you can sometimes make the whiskeys smoother to taste!


Willett Distilling Co.

The historic Willett Distilling Co. is southeast of downtown Bardstown. It was founded by Thomas Willett in 1935. The extended family still owns and operates the distillery, which they re-established in 1984, using water from two springs located on its 120-acre site. They make a number of whiskeys, including the Willett Family Estate Bottled Rye and Bourbon and the Johnny Drum Private Stock. Though the Rye was good, my favorite was the smooth Pot Still Reserve, which I am enjoying at home in Chicago. 1869 Loretto Road.

Located southwest of downtown Bardstown at 300 Barton Road is the Barton 1792 Distillery. The site has 29 historic rickhouses on the grounds of this distillery that was established by Thomas Moore in 1879. It uses the same limestone springs that its founder used to make bourbon more than 100 years ago. I highly recommend the Single Barrel 1792, which now sits on my new bourbon bar in Chicago.


Barton 1792 Distillery.


Old Talbott Tavern, Bardstown.

Not to be missed is the Old Talbott Tavern, a charming restaurant in a historic pub from 1799 located in one of the oldest western stagecoach stops in the country.

Louisville, Kentucky

Louisville is made up of a number of neighborhoods made for exploring. Many are emerging with collections of restaurants, bar, shops, and galleries.

Don’t miss Whiskey Row/Museum Row/Downtown Louisville for hotels, shopping and restaurants. NULU, or New Louisville, is the emerging area along East Market Street with a growing number of art galleries, antique shops, specialty stores, bars, microbreweries, and restaurants. Butchertown, just northeast of downtown, is one of Louisville’s oldest neighborhoods. It was the city’s original meatpacking district with butcher shops dominating the area in the 1800s. It is now undergoing a new renaissance.

Bardstown Road is located in the city’s Highlands neighborhood. It is a big dining and nightlife destination along with an eclectic collection of shops. There is a great mix of restaurants, bars, shops, and galleries along Frankfort Avenue. It is a fun place to just wander, grab a great meal, and enjoy your time in the neighborhood. Portland is on the western edge of downtown Louisville, a growing area with new businesses and residents. Make sure to drive through this historic neighborhood south of downtown. It has the largest collection of restored Victorian homes in America and is the third largest Historical Preservation District in the country, covering 48 city blocks.

Highlights include:

Angel’s Envy

At 500 East Main, this urban distillery is where I enjoyed one of my favorite tours and tastings. You see their distillation process from beginning to end, with the tour culminating in the distillery bar, The Finishing Room. They make a rye whiskey finished in rum barrels, a bourbon-aged in port wine barrels, and a Cask Strength Bourbon aged in port barrels. This was my favorite and I am now enjoying it on cold Chicago nights by the fire.


Angel’s Envy.

Bulleit Bourbon

At 3860 Fitzgerald Road, The Bulleit Experience at the Stitzel-Weller Distillery is a must-see when you are in Louisville. After my visit, I have become a big fan. The old Bulleit family recipe for bourbon was revived in 1987 by Thomas E. Bulleit, Jr. His great-great-grandfather, Augustus Bulleit, made a high-rye whiskey between 1830 and 1860. Today there are three Bulleit Frontier Whiskeys: the Bulleit Bourbon, the Small Batch Bulleit Rye, and the Aged 10 Years Bulleit Bourbon. Tours are available, but you can also walk around the grounds and peek into the historic buildings without signing up for a guided tour. I opted for the latter and enjoyed my time there.


Bulleit Bourbon.

Peerless Distilling Company

Peerless is Louisville’s newest distillery, located downtown at 120 North 10th Street. Henry Kraver’s first bourbon went into the barrel in 1889. His great-grandson Corky Taylor and his son Carson have revived the family business using the original process. They currently make a rye whiskey, and their bourbon will be ready in the spring of 2019. Tours of this urban distillery are available.

Churchill Downs

This famous spot is home to the famed Kentucky Derby horse race in early May of each year. But you don’t have to fight the Derby crowds of over 165,000 people to experience the historic site from 1875. Beginning just before the Derby in late April through June, and then September and later in October to early December, there are races most weeks from Wednesday through Sunday. You can see the races, visit the track, enjoy the food, and experience the Kentucky Derby without the crowds.


Churchill Downs.


High speeds at Churchill Downs.

Next to the racetrack is a two-story Kentucky Derby Museum with exhibits on past winners and the experience of the Derby. They have a nice restaurant, the Derby Cafe, where you can grab a bite and a piece of the famous Derby Pie. The highlight is a 360-degree multimedia film highlighting the entire day of the Kentucky Derby. 704 Central Ave.

Speed Art Museum

Once you have had enough bourbon, visit the Speed Art Museum. Reopened in 2016 after a major makeover, Speed features art from ancient cultures, African art, Native American art, European and American art, and contemporary art and photography. They also have a large collection of Kentucky furniture, paintings, ceramics, decorative accessories, and textiles. 2035 South 3rd.  

Louisville, Kentucky is gaining a reputation as a great food city. From casual cafes to fine dining restaurants, you have many great options to choose from. My top finds include:


Located at 316 West Main, this popular spot by famed Louisville chef, Edward Lee, merges Southern food with Asian ingredients at this hip restaurant and bar.

Harvest Restaurant

This is an excellent restaurant featuring locally sourced ingredients and over 70 varieties of Kentucky bourbon. I thoroughly enjoyed the experience along with a great conversation with Jim McArthur, one of the owners, who is delightful. 624 East Market.

Butchertown Grocery, a fine dining restaurant in a historic building from the 1800s that was a former grocery store. It has a fun bar/lounge upstairs, Lola, that is reminiscent of an old speakeasy. I was there for dinner and highly recommend it. It serves New American fare and artisanal cocktails. 1076 East Washington.

Copper & Kings American Brandy

Before or after your meal at Butchertown Grocery, make sure to visit this local brandy distillery located at 1121 East Washington Street. I had a great experience taking a tour and tasting their wonderful spirits including brandies, gin, and absinthe. I loved trying their three American brandies. They also feature special events from music performances and movie nights to cigar and food events. Onsite, don’t miss the B-Town Pie Company for meat and savory pies, sides, dessert pies, and ice cream.

Jack Fry’s

Established by Jack Fry and his wife, Flossie, at 1007 Bardstown Road in 1933, this popular local sportsman’s hangout was open until 1972. After being vacant for several years followed by another concept, it was re-established as Jack Fry’s in 1987. It continues today as a staple of Louisville’s culinary scene and has been featured in a number of national magazines and newspapers from the New York Times to Bon Appetit and Southern Living. The shrimp and grits were perfect. The dining room with its old photographs is a classic as well.


Jack Fry’s, Louisville.

610 Magnolia

This is Edward Lee’s fine dining restaurant in the Old Louisville Neighborhood. It features innovative/modern Southern cuisine. They offer a four-course and six-course tasting menu with or without wine pairings. Chef Lee has been a finalist for the James Beard Award for Best Chef Southwest. The restaurant has been featured in Bon Appetit, Food & Wine, The New York Times Magazine, Saveur, Southern Living, Esquire, Wine Enthusiast, and many other national publications.

Proof on Main

Make sure to try Proof on Main, which is the restaurant in the 21c Hotel. It is open for breakfast, lunch, dinner, and weekend brunch. Esquire Magazine named it one of the Best New Restaurants in 2006. 702 West Main.

Blue Dog Bakery & Café

This is a local bakery and cafe that features its own artisan breads and pastries. I enjoyed a wonderful lunch with smoked salmon tartine with boursin and cucumber along with a wheat berry salad. 2868 Frankfort Avenue.

To stay I recommend the 21c Museum Hotel. This is the flagship of this small boutique hotel chain. It is located at 700 West Main along Museum Row. In addition to its 91 rooms, it has an emphasis on contemporary art: the hotel has 9,000 sq. ft. of exhibition space that features exhibitions by contemporary artists. You feel like you are staying in a contemporary art museum. The galleries are free and open to the public 24 hours a day. Each of their hotels feature large, colorful plastic penguins. Their color is red in Louisville! Look for them throughout the lobby, halls, elevators, restaurant, and exhibition spaces.


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