Weekend Getaways in Kentucky

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

124 itineraries

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

Prairie Light & Quiet Stars: 3 Days Alone in Land Between the Lakes

3 Days · Solo

Land Between the Lakes (KY side), Kentucky

Prairie Light & Quiet Stars: 3 Days Alone in Land Between the Lakes

6 stops

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

2 Days · Active Retirees

Land Between the Lakes (KY side), Kentucky

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

4 stops

Prairie Dust & Prairie Skies: 3 Days in Land Between the Lakes

3 Days · Teen Families

Land Between the Lakes (KY side), Kentucky

Prairie Dust & Prairie Skies: 3 Days in Land Between the Lakes

6 stops

Elk, Stars, and Slow Water: 3 Days in Land Between the Lakes

3 Days · Teen Families

Land Between the Lakes (KY side), Kentucky

Elk, Stars, and Slow Water: 3 Days in Land Between the Lakes

6 stops

Prairie Light & Quiet Stars: 3 Days Alone in Land Between the Lakes

3 Days · Solo

Land Between the Lakes (KY side), Kentucky

Prairie Light & Quiet Stars: 3 Days Alone in Land Between the Lakes

6 stops

Prairie Light & Quiet Stars: Two Days in Land Between the Lakes

2 Days · Active Retirees

Land Between the Lakes (KY side), Kentucky

Prairie Light & Quiet Stars: Two Days in Land Between the Lakes

4 stops

Elk, Stars, and Still Water: 2 Days at Land Between the Lakes

2 Days · Young Families

Land Between the Lakes (KY side), Kentucky

Elk, Stars, and Still Water: 2 Days at Land Between the Lakes

4 stops

Prairie Mornings & Starlit Evenings: A Family Weekend in Land Between the Lakes

2 Days · Young Families

Land Between the Lakes (KY side), Kentucky

Prairie Mornings & Starlit Evenings: A Family Weekend in Land Between the Lakes

4 stops

Prairie Light & Still Water: 3 Days Between the Lakes

3 Days · Active Retirees

Land Between the Lakes (KY side), Kentucky

Prairie Light & Still Water: 3 Days Between the Lakes

5 stops

Falls, Fog, and Frontier Ridgelines: Two Days Solo in Daniel Boone National Forest

2 Days · Solo

Daniel Boone NF (Stearns, London), Kentucky

Falls, Fog, and Frontier Ridgelines: Two Days Solo in Daniel Boone National Forest

5 stops

Waterfalls, Wheels & Wild Ridgelines: 2 Days in Daniel Boone National Forest

2 Days · Teen Families

Daniel Boone NF (Stearns, London), Kentucky

Waterfalls, Wheels & Wild Ridgelines: 2 Days in Daniel Boone National Forest

4 stops

Prairie Light & Quiet Water: Two Days in Land Between the Lakes

2 Days · Couples

Land Between the Lakes (KY side), Kentucky

Prairie Light & Quiet Water: Two Days in Land Between the Lakes

4 stops

Falls, Rails & Firelight: 2 Days in Daniel Boone National Forest

2 Days · Teen Families

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails & Firelight: 2 Days in Daniel Boone National Forest

4 stops

Prairie Mornings & Starlit Evenings: 3 Days at Land Between the Lakes

3 Days · Young Families

Land Between the Lakes (KY side), Kentucky

Prairie Mornings & Starlit Evenings: 3 Days at Land Between the Lakes

4 stops

Falls, Mist, and Mountain Rails: Two Gentle Days in Daniel Boone National Forest

2 Days · Active Retirees

Daniel Boone NF (Stearns, London), Kentucky

Falls, Mist, and Mountain Rails: Two Gentle Days in Daniel Boone National Forest

3 stops

Stone Arches & Ridge Light: 3 Days in Red River Gorge

3 Days · Teen Families

Red River Gorge (Slade area), Kentucky

Stone Arches & Ridge Light: 3 Days in Red River Gorge

4 stops

Sandstone Solitude: Three Days Alone with Kentucky's Wild Arches

3 Days · Solo

Red River Gorge (Slade area), Kentucky

Sandstone Solitude: Three Days Alone with Kentucky's Wild Arches

6 stops

Falls, Fog, and Firelight: A Solo Wander Through Daniel Boone National Forest

3 Days · Solo

Daniel Boone NF (Stearns, London), Kentucky

Falls, Fog, and Firelight: A Solo Wander Through Daniel Boone National Forest

8 stops

Frozen Niagara & Quiet River Light: Two Days at Mammoth Cave

2 Days · Active Retirees

Mammoth Cave area, Kentucky

Frozen Niagara & Quiet River Light: Two Days at Mammoth Cave

4 stops

Underground Light: Three Days Alone with Mammoth Cave

3 Days · Solo

Mammoth Cave area, Kentucky

Underground Light: Three Days Alone with Mammoth Cave

8 stops

Showing 60 of 124 — explore all of Kentucky.

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