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Bourbon Trails, Whiskey Bars & Live Music

Explore the Southern traditions of whiskey, music and the places that inspired both. Visit historic distilleries, small-town bars and mountain music venues where local players still tell stories through song. Follow the backroads between tastings and performances, uncovering the small towns and time-worn venues keep Southern traditions alive.

Bourbon & B-sides

What To Expect

  • Kentucky and Tennessee’s bourbon towns, music communities and scenic backroads.

  • A journey combining distilleries, live music, historic Main Streets and unexpected local discoveries.

  • Boutique hotels, historic inns, locally owned stays and character accommodation.

  • Rolling countryside, easy drives and time built in for tastings, meals and exploring.

  • Ideal for travellers drawn to whiskey, music history, small towns and authentic local experiences.

Worth Checking In

From historic inns to character-filled hotels, these are the places we love for their sense of place, thoughtful details and Southern hospitality.

SECRET STAYS

The Manchester Lexington

Lexington, KY

The Bourbon Inn

Paris, KY

The Woodford Hotel

Versailles, KY

Bourbon Barrel Cottages

Lawrenceburg, KY

Bourbon Manor Bed & Breakfast Inn

Bardstown, KY

Historic Boone Tavern Hotel

Berea, KY

The Kentucky Grand Hotel

Bowling Green, KY

Historic Homes

Leiper's Fork, TN

The Gunner Runner

Florence, AL

Hotel Tupelo

Tupelo, MS

The Shack Up Inn

Clarksdale, MS

Big Cypress Lodge

Memphis, TN

Worth Checking Out

A collection of places to explore and things to experience that reveal a little more of what makes the region special, where to eat, what to do beyond the usual tourist trail.

LOCAL EXPERIENCES

Explore the Distillery District

Lexington, KY
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Claiborne Farm

Paris, KY
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Glenns Creek Distilling

Versailles, KY
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Larrikin Bourbon Company

Lawrenceburg, KY
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Kentucky Dinner Train Bourbon Excursion

Bardstown, KY
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Renfro Valley Entertainment Center

Berea, KY
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Dueling Grounds Distillery

Bowling Green, KY
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Leiper's Fork Distillery

Leiper's Fork, TN
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For The Record

Florence, AL
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Elvis Presley Birthplace & Museum

Tupelo, MS
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Delta Blues Museum & the Crossroads

Clarksdale, MS
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Sun Studio

Memphis, TN
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OBC Kitchen
Lexington, KY
Jerrys Restaurant
Paris, KY
The Amsden Bourbon Bar
Versailles, KY
Heaven's to Betsy Bakery & Deli
Lawrenceburg, KY
The Bar at Willett
Bardstown, KY
Crafted at Boone Tavern
Berea, KY
White Squirrel Brewery
Bowling Green, KY
Fox & Locke
Leiper's Fork, TN
Odette
Florence, AL
Blue Canoe
Tupelo, MS
Ground Zero Blues Club
Clarksdale, MS
Big Cypress Lodge
Memphis, TN
PLAN YOUR TRIP

Make this Trip Yours

Turn these ideas into a real journey. Start planning your trip and create a route around the places, stays and experiences that inspire you most.

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