Weekend Getaways in Kentucky

Short trips with every day mapped out — verified attractions, realistic pacing, and food along the way across 9 destinations.

144 itineraries

Murals, Quilts & River Light: 2 Days in Paducah

2 Days · Teen Families

Paducah area, Kentucky

Murals, Quilts & River Light: 2 Days in Paducah

5 stops

Bourbon, Bricks & Backstreets: A Solo Weekend in Louisville

2 Days · Solo

Louisville, Kentucky, Kentucky

Bourbon, Bricks & Backstreets: A Solo Weekend in Louisville

8 stops

Bourbon, Bats & Big Lawns: Two Fall Days in Louisville

2 Days · Teen Families

Louisville, Kentucky, Kentucky

Bourbon, Bats & Big Lawns: Two Fall Days in Louisville

7 stops

Murals, Thread, and River Light: Two Fall Days in Paducah

2 Days · Teen Families

Paducah area, Kentucky

Murals, Thread, and River Light: Two Fall Days in Paducah

7 stops

Bourbon, Bats, and the River's Quiet Pulse: 2 Days in Louisville

2 Days · Solo

Louisville, Kentucky, Kentucky

Bourbon, Bats, and the River's Quiet Pulse: 2 Days in Louisville

9 stops

Quilts, Color & Quiet Water: Two Days Alone in Paducah

2 Days · Solo

Paducah area, Kentucky

Quilts, Color & Quiet Water: Two Days Alone in Paducah

9 stops

Bourbon, Bats & Riverfront Light: 2 Days in Louisville with Teens

2 Days · Teen Families

Louisville, Kentucky, Kentucky

Bourbon, Bats & Riverfront Light: 2 Days in Louisville with Teens

7 stops

Where Three States Meet: Two Mountain Days at Cumberland Gap

2 Days · Active Retirees

Cumberland Gap NHP, Kentucky

Where Three States Meet: Two Mountain Days at Cumberland Gap

5 stops

Ridgeline Solitude: 3 Days Walking the Cumberland Gap

3 Days · Solo

Cumberland Gap NHP, Kentucky

Ridgeline Solitude: 3 Days Walking the Cumberland Gap

9 stops

Three States, One Gap: A Family Passage Through Cumberland

3 Days · Teen Families

Cumberland Gap NHP, Kentucky

Three States, One Gap: A Family Passage Through Cumberland

7 stops

Bourbon Light & River Walks: Two Easy Days in Louisville

2 Days · Active Retirees

Louisville, Kentucky, Kentucky

Bourbon Light & River Walks: Two Easy Days in Louisville

6 stops

Ridgeline Solitude: 3 Days Through the Cumberland Gap

3 Days · Solo

Cumberland Gap NHP, Kentucky

Ridgeline Solitude: 3 Days Through the Cumberland Gap

9 stops

Where Three States Meet: A Gentle Passage Through Cumberland Gap

2 Days · Active Retirees

Cumberland Gap NHP, Kentucky

Where Three States Meet: A Gentle Passage Through Cumberland Gap

5 stops

Log Cabins & Mountain Passes: A Family Weekend at Cumberland Gap

2 Days · Young Families

Cumberland Gap NHP, Kentucky

Log Cabins & Mountain Passes: A Family Weekend at Cumberland Gap

3 stops

Where Three States Meet: A Cumberland Gap Escape for Two

2 Days · Couples

Cumberland Gap NHP, Kentucky

Where Three States Meet: A Cumberland Gap Escape for Two

6 stops

Where Three States Meet: Two Days of Ridge Light and Frontier Hush

2 Days · Couples

Cumberland Gap NHP, Kentucky

Where Three States Meet: Two Days of Ridge Light and Frontier Hush

6 stops

Where Three States Meet: Three Slow Days at Cumberland Gap

3 Days · Active Retirees

Cumberland Gap NHP, Kentucky

Where Three States Meet: Three Slow Days at Cumberland Gap

6 stops

Through the Gap: Two Easy Days of Frontier Wonder for Little Explorers

2 Days · Young Families

Cumberland Gap NHP, Kentucky

Through the Gap: Two Easy Days of Frontier Wonder for Little Explorers

3 stops

Elk, Stars, and Still Water: Two Fall Days in Land Between the Lakes

2 Days · Teen Families

Land Between the Lakes (KY side), Kentucky

Elk, Stars, and Still Water: Two Fall Days in Land Between the Lakes

4 stops

Ridgeline & Rustic Light: 3 Days in Cumberland Gap

3 Days · Couples

Cumberland Gap NHP, Kentucky

Ridgeline & Rustic Light: 3 Days in Cumberland Gap

8 stops

Misty Ridges & Little Legs: 3 Days at Cumberland Gap

3 Days · Young Families

Cumberland Gap NHP, Kentucky

Misty Ridges & Little Legs: 3 Days at Cumberland Gap

6 stops

Where Three States Meet: A Cumberland Gap Escape for Two

3 Days · Couples

Cumberland Gap NHP, Kentucky

Where Three States Meet: A Cumberland Gap Escape for Two

6 stops

Bluegrass Notes & River Light: 2 Days in Owensboro

2 Days · Teen Families

Owensboro area, Kentucky

Bluegrass Notes & River Light: 2 Days in Owensboro

5 stops

Sandstone Skylines: Two Days Chasing Arches in the Red River Gorge

2 Days · Teen Families

Red River Gorge (Slade area), Kentucky

Sandstone Skylines: Two Days Chasing Arches in the Red River Gorge

4 stops

Underground Cathedrals: Two Days Beneath and Beside Mammoth Cave

2 Days · Teen Families

Mammoth Cave area, Kentucky

Underground Cathedrals: Two Days Beneath and Beside Mammoth Cave

4 stops

Underground Rivers & Bluegrass Quiet: 2 Days at Mammoth Cave

2 Days · Solo

Mammoth Cave area, Kentucky

Underground Rivers & Bluegrass Quiet: 2 Days at Mammoth Cave

4 stops

Sandstone Solitude: Two Days Alone in the Red River Gorge

2 Days · Solo

Red River Gorge (Slade area), Kentucky

Sandstone Solitude: Two Days Alone in the Red River Gorge

4 stops

Stone Arches & Ridgeline Views: A Winter Weekend in Red River Gorge

2 Days · Teen Families

Red River Gorge (Slade area), Kentucky

Stone Arches & Ridgeline Views: A Winter Weekend in Red River Gorge

4 stops

Underground Cathedrals: Two Days Alone in Mammoth Cave

2 Days · Solo

Mammoth Cave area, Kentucky

Underground Cathedrals: Two Days Alone in Mammoth Cave

4 stops

Stone Arches & Solitude: Two Days in the Red River Gorge

2 Days · Solo

Red River Gorge (Slade area), Kentucky

Stone Arches & Solitude: Two Days in the Red River Gorge

4 stops

Bluegrass Strings & River Smoke: 2 Days in Owensboro

2 Days · Solo

Owensboro area, Kentucky

Bluegrass Strings & River Smoke: 2 Days in Owensboro

5 stops

Underground Rivers & Limestone Light: 2 Days at Mammoth Cave

2 Days · Teen Families

Mammoth Cave area, Kentucky

Underground Rivers & Limestone Light: 2 Days at Mammoth Cave

4 stops

Murals, Mansions & River Light: 3 Days in Paducah

3 Days · Teen Families

Paducah area, Kentucky

Murals, Mansions & River Light: 3 Days in Paducah

9 stops

Quilts, Murals & River Light: 3 Days Alone in Paducah

3 Days · Solo

Paducah area, Kentucky

Quilts, Murals & River Light: 3 Days Alone in Paducah

9 stops

Bluegrass Strings & River Light: 3 Days in Owensboro

3 Days · Solo

Owensboro area, Kentucky

Bluegrass Strings & River Light: 3 Days in Owensboro

9 stops

Quilts, Murals & the Ohio's Slow Current: Two Days in Paducah

2 Days · Active Retirees

Paducah area, Kentucky

Quilts, Murals & the Ohio's Slow Current: Two Days in Paducah

5 stops

Bourbon, Bat Cracks & River Light: 3 Days in Louisville with Teens

3 Days · Teen Families

Louisville, Kentucky, Kentucky

Bourbon, Bat Cracks & River Light: 3 Days in Louisville with Teens

9 stops

Quilts, Murals & River Light: 3 Days Alone in Paducah

3 Days · Solo

Paducah area, Kentucky

Quilts, Murals & River Light: 3 Days Alone in Paducah

8 stops

Bourbon, Bat Cracks & Victorian Whispers: 3 Days Solo in Louisville

3 Days · Solo

Louisville, Kentucky, Kentucky

Bourbon, Bat Cracks & Victorian Whispers: 3 Days Solo in Louisville

10 stops

Murals, Mansions & River Light: 3 Days in Paducah

3 Days · Teen Families

Paducah area, Kentucky

Murals, Mansions & River Light: 3 Days in Paducah

9 stops

Bourbon, Bricks & Riverlight: Two Unhurried Days in Louisville

2 Days · Active Retirees

Louisville, Kentucky, Kentucky

Bourbon, Bricks & Riverlight: Two Unhurried Days in Louisville

5 stops

Quilts, Murals & Slow River Light: Two Days in Paducah

2 Days · Active Retirees

Paducah area, Kentucky

Quilts, Murals & Slow River Light: Two Days in Paducah

5 stops

Quilts, Murals & River Light: 2 Days in Paducah

2 Days · Couples

Paducah area, Kentucky

Quilts, Murals & River Light: 2 Days in Paducah

7 stops

River Songs & Slow Smoke: Two Family Days in Owensboro

2 Days · Young Families

Owensboro area, Kentucky

River Songs & Slow Smoke: Two Family Days in Owensboro

5 stops

Riverbends & Rainbow Walls: A Slow Paducah Weekend for Little Explorers

2 Days · Young Families

Paducah area, Kentucky

Riverbends & Rainbow Walls: A Slow Paducah Weekend for Little Explorers

4 stops

Bourbon, Bridges & Victorian Whispers: 2 Days in Louisville

2 Days · Couples

Louisville, Kentucky, Kentucky

Bourbon, Bridges & Victorian Whispers: 2 Days in Louisville

7 stops

Slow Bourbon Days: Louisville with Little Ones

2 Days · Young Families

Louisville, Kentucky, Kentucky

Slow Bourbon Days: Louisville with Little Ones

4 stops

River Light & Quiet Corners: Two Fall Days in Paducah

2 Days · Couples

Paducah area, Kentucky

River Light & Quiet Corners: Two Fall Days in Paducah

7 stops

Bourbon Light & River Time: Three Unhurried Days in Louisville

3 Days · Active Retirees

Louisville, Kentucky, Kentucky

Bourbon Light & River Time: Three Unhurried Days in Louisville

7 stops

Slow Mornings & River Play: 2 Days in Louisville with Little Ones

2 Days · Young Families

Louisville, Kentucky, Kentucky

Slow Mornings & River Play: 2 Days in Louisville with Little Ones

4 stops

Quilts, Murals & River Light: 3 Days in Paducah

3 Days · Active Retirees

Paducah area, Kentucky

Quilts, Murals & River Light: 3 Days in Paducah

7 stops

Bourbon Light & River Time: 3 Days in Louisville

3 Days · Active Retirees

Louisville, Kentucky, Kentucky

Bourbon Light & River Time: 3 Days in Louisville

6 stops

Bourbon, Bridges & Bluegrass: Two Days for Two in Louisville

2 Days · Couples

Louisville, Kentucky, Kentucky

Bourbon, Bridges & Bluegrass: Two Days for Two in Louisville

8 stops

Murals, Quilts & River Light: A Slow-Paced Paducah Weekend for Little Explorers

2 Days · Young Families

Paducah area, Kentucky

Murals, Quilts & River Light: A Slow-Paced Paducah Weekend for Little Explorers

4 stops

Prairie Light & Star Fields: 2 Days at Land Between the Lakes

2 Days · Teen Families

Land Between the Lakes (KY side), Kentucky

Prairie Light & Star Fields: 2 Days at Land Between the Lakes

4 stops

Slow River Days: A Family Introduction to Louisville

3 Days · Young Families

Louisville, Kentucky, Kentucky

Slow River Days: A Family Introduction to Louisville

6 stops

Riverbend Wonder: A Slow Family Weekend in Paducah

3 Days · Young Families

Paducah area, Kentucky

Riverbend Wonder: A Slow Family Weekend in Paducah

6 stops

Bourbon, Bridges & Bluegrass Nights: 3 Days in Louisville

3 Days · Couples

Louisville, Kentucky, Kentucky

Bourbon, Bridges & Bluegrass Nights: 3 Days in Louisville

9 stops

Bourbon Barrels & Big Lawns: 3 Slow Days in Louisville with Little Ones

3 Days · Young Families

Louisville, Kentucky, Kentucky

Bourbon Barrels & Big Lawns: 3 Slow Days in Louisville with Little Ones

6 stops

River Light & Quiet Streets: Three Days in Paducah

3 Days · Couples

Paducah area, Kentucky

River Light & Quiet Streets: Three Days in Paducah

9 stops

Showing 60 of 144 — explore all of Kentucky.

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