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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.

SECRET STAYS

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.

Historic Eureka Inn

Jonesborough, TN

The Manchester Lexington

Lexington, KY

The Woodford Hotel

Versailles, KY

Bourbon Barrel Cottages

Lawrenceburg, KY

Bourbon Manor Bed & Breakfast Inn

Bardstown, KY

The Kentucky Grand Hotel

Bowling Green, KY

The Gunner Runner

Florence, AL

Hotel Tupelo

Tupelo, MS

The Shack Up Inn

Clarksdale, MS

Big Cypress Lodge

Memphis, TN

LOCAL EXPERIENCES

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.

Slugger Museum

Louisville, KY

Jerrys Restaurant

Paris, KY

Club Ebony

Indianola, MS

Fox & Locke

Leipers Fork, TN

Claiborne Farm

Paris, KY

White Squirrel Brewery

Bowling Green, KY

Delta Blues Museum & The Cross Roads

Clarksdale, MS

The Blue Canoe Bar

Tupelo, MS

Ground Zero Blues Club

Clarksdale, MS

Kentucky Dinner Train

Bardstown, KY

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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