DAY 1

James B. Beam Distilling Co. — Where Family Tradition Meets Innovation

Start your adventure at the James B. Beam Distilling Co., where seven generations of family tradition meet state-of-the-art innovation. No trip to Beam is complete without savoring a cocktail or Southern-inspired fare at The Kitchen Table Restaurant. Keep an eye out for the many special events and Master Distiller dinners they host throughout the year.

Pro Tip: If you’re using the Bourbon Audio Tour from High Proof Productions, start it here (James B. Beam) before you hit the road. You’ll enjoy storytelling, local interviews, and Bourbon history that accompany your drive — a one-of-a-kind sensory experience.

Before leaving Bullitt County, stop by the Shepherdsville-Bullitt County Tourism office for local dining tips and regional highlights, including the Wine, Whiskey & Ale Trail and the 16,000-acre Bernheim Forest & Arboretum.

Fun Fact: Isaac Wolfe Bernheim, founder of IW Harper Bourbon, built a distillery now owned and operated by Heaven Hill.

Next, visit Four Roses Warehouse & Bottling Facility for a guided tasting in their cozy visitor center. Find your favorite of their ten unique recipes and explore their single-story rickhouses, which are unusual in the Bourbon industry. Don’t forget to snap a photo in front of their giant Bourbon barrel.

As you make your way towards Bardstown, there’s no better way to round out your Bourbon Trail™ trip than by spending a night at The Samuels House. Constructed circa 1820 by John Samuels, this premium vacation lodging showcases the Maker’s Mark family legacy. Every room tells a story, and guests can elevate their stay with an in-house chef experience or a private tasting with Kentucky Bourbon Hall of Fame legend Bill Samuels, Jr.

DAY 2

Begin day 2 at Preservation Distillery, an artisanal operation housed on a picturesque farm complete with longhorn cattle. Sip on their award-winning whiskies and learn about the origin of the highly sought after Very Olde Saint Nick.

Heaven Hill Bourbon Experience — Five Brothers, One Legacy

Continue to the award-winning Heaven Hill Bourbon Experience where interactive exhibits and guided tastings bring the Shapira family story to life. Enjoy lunch and cocktails at Five Brothers Bar & Kitchen, known for elevated comfort food. You can even bottle your own exclusive whiskey or visit the new Heaven Hill Springs Distillery.

Continue into the picturesque downtown, home of Chicken Cock Whiskey Circa 1856, one of America’s oldest brands reborn in Bardstown. Grab a handcrafted cocktail and relax under their towering oak tree before heading to dinner.

End your evening at the historic Old Talbott Tavern, where legends like Jesse James once dined. Enjoy a classic Kentucky hot brown and their famous fried green tomatoes before having a nightcap in the world’s oldest Bourbon bar. 

Check into The Trail Hotel, a Bourbon-themed boutique stay with a heated outdoor pool, golf simulators, and recovery spa. Ask the Bourbon Butler for insider tips…and maybe directions to their secret speakeasy. Dinner and drinks at Oak & Ember are a must.

DAY 3

Bardstown Bourbon Company — Where Innovation Meets Tradition

Kick off your morning at Bardstown Bourbon Company, blending modern design with heritage craftsmanship. Choose from one of seven immersive tours, then enjoy a farm-to-table lunch at the Kitchen & Bar either inside their stunning dining room or on the patio overlooking the rickhouses.

Lux Row Distillers — Real Roots, Real Family, Real Products

Just down the road is Lux Row Distillers – set in a breathtaking landscape of rolling hills and rickhouses. Speaking of rickhouses, don’t miss the major photo op moment against their towering barrel wall in Rickhouse 1.  Lux Row is home to brands you know and love like Ezra Brooks, Rebel, and the limited release Blood Oath series. 

If golf is your game, spend your afternoon on the greens at Bardstown Country Club, proud  member of the Kentucky Golf Trail.

Looking for a place to stay with a group? The Driscoll Estate offers the perfect home base for weddings, retreats, and Bourbon getaways. Whether you’re planning a dream wedding, a corporate escape, or a relaxing weekend in the country, their team helps bring every vision to life. 

DAY 4

Start your day at Kentucky Cooperage, where skilled craftsmen hand-build and char each barrel, giving Bourbon about 90% of its color and flavor. You’ll leave with that signature “Kentucky Cologne” campfire aroma on your clothes.

Continue to Limestone Branch Distillery, where the Beam family’s craft continues in small-batch form. Sip Yellowstone Bourbon, an 1872 family brand revived by Steve Beam and now partnered with the National Park Conservation Association to help preserve and protect our public lands.

Maker’s Mark Distillery — Artistry in Every Drop

Follow the winding trail to Maker’s Mark Distillery, a true icon of Kentucky hospitality. Take a tour, dip your own bottle in red wax, and see how barrels of Maker’s 46 are finished in their cool, limestone cellar. Enjoy lunch at Star Hill Provisions, where farm-fresh dishes are perfectly paired with cocktails made at the source. Stroll the grounds to see their gardens, apiary, mushroom logs, and nature trails, part of Maker’s Mark’s B Corp commitment to sustainability.

Fun Fact – if you’re a tree or science nerd, you will love a visit to the mother tree used in the white oak genome mapping project with the University of Kentucky.

Wrap up the day at Log Still Distillery, home to the Monk’s Road series of Bourbons, ryes, and gins. Their onsite music venue, The Amp, hosts world-famous artists like Lady A, Elle King, and Dwight Yoakam. Extend your stay in one of their elegant on-site accommodations for a perfect evening under the stars.

DAY 5

Finish your Bardstown adventure at Boundary Oak Distillery, located just outside Fort Knox. Known for its patriotic spirit, Boundary Oak crafts small-batch bottlings honoring American heroes like General George Patton and Abraham Lincoln. Don’t miss a sip of their bestselling lavender whiskey.

Then raise one last glass at WhistlePig Distillery, where whiskey innovation meets Kentucky tradition…

Extras Worth the Stop

Before you head home, make your way to downtown Bloomfield. Explore Nettie Jarvis Antiques, a treasure trove of Kentucky charm, and grab a drink at the adjoining Rowdy’s Bourbon Bar. Then cross the street to Ernie’s Tavern for dinner and live music (on weekends). Bowl a few frames next door, enjoy an ice cream cone, and browse Hollywood memorabilia from Top Gun, Pirates of the Caribbean, and National Treasure.

Fun Fact: Much of Bloomfield’s downtown was lovingly restored by Linda Bruckheimer, wife of famed movie producer Jerry Bruckheimer (inquire about private event rentals).

Ever wondered what it means to invest in Bourbon beyond your collection of bottles? CaskX allows enthusiasts to own a piece of the aging process itself—investing directly in Bourbon barrels from respected Kentucky distilleries. It’s more than a financial opportunity; it’s a way to support the craftsmanship, patience, and tradition that shape every pour. 

More to Explore

Bardstown is just the beginning of your Kentucky Bourbon journey. With its rich history, scenic rickhouses, and world-class distilleries, this region offers an unparalleled Bourbon experience, but there’s much more to discover across the state. From the rolling hills of the Lexington area to the historic distilleries along the Louisville corridor, each region brings its own flavor, stories, and signature pours. Consider expanding your adventure to explore additional Kentucky Bourbon Trail® regions – each corner of the state has a new story waiting in every glass.