Weekend Getaways in Kentucky

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

68 itineraries

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

Stone Arches & Ridge Winds: 3 Winter Days in Red River Gorge

3 Days · Teen Families

Red River Gorge (Slade area), Kentucky

Stone Arches & Ridge Winds: 3 Winter Days in Red River Gorge

4 stops

Stone Arches & Solitude: 3 Winter Days in the Red River Gorge

3 Days · Solo

Red River Gorge (Slade area), Kentucky

Stone Arches & Solitude: 3 Winter Days in the Red River Gorge

5 stops

Descent Into Deep Time: 3 Days Beneath Mammoth Cave

3 Days · Teen Families

Mammoth Cave area, Kentucky

Descent Into Deep Time: 3 Days Beneath Mammoth Cave

6 stops

Stone Arches & Slow Mornings: A Gentle Weekend in Red River Gorge

2 Days · Active Retirees

Red River Gorge (Slade area), Kentucky

Stone Arches & Slow Mornings: A Gentle Weekend in Red River Gorge

3 stops

Falls, Rails, and Ridgeline Light: Two Days in Daniel Boone National Forest

2 Days · Active Retirees

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails, and Ridgeline Light: Two Days in Daniel Boone National Forest

4 stops

Underground Rivers & Limestone Silence: 3 Days at Mammoth Cave

3 Days · Solo

Mammoth Cave area, Kentucky

Underground Rivers & Limestone Silence: 3 Days at Mammoth Cave

9 stops

Falls, Rails & Wildflowers: 3 Days in Daniel Boone National Forest

3 Days · Teen Families

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails & Wildflowers: 3 Days in Daniel Boone National Forest

6 stops

Frozen Niagara & River Light: Two Days in Mammoth Cave Country

2 Days · Active Retirees

Mammoth Cave area, Kentucky

Frozen Niagara & River Light: Two Days in Mammoth Cave Country

4 stops

Underground Light, Bluegrass Nights: Two Days at Mammoth Cave

2 Days · Couples

Mammoth Cave area, Kentucky

Underground Light, Bluegrass Nights: Two Days at Mammoth Cave

4 stops

Waterfalls, Whistles & Wildflowers: A Gentle Family Weekend in Daniel Boone National Forest

2 Days · Young Families

Daniel Boone NF (Stearns, London), Kentucky

Waterfalls, Whistles & Wildflowers: A Gentle Family Weekend in Daniel Boone National Forest

4 stops

Underground Light, Riverbound Nights: Two Days at Mammoth Cave

2 Days · Couples

Mammoth Cave area, Kentucky

Underground Light, Riverbound Nights: Two Days at Mammoth Cave

4 stops

Stone Arches & Slow Mornings: 3 Days Amid Kentucky's Ancient Sandstone

3 Days · Active Retirees

Red River Gorge (Slade area), Kentucky

Stone Arches & Slow Mornings: 3 Days Amid Kentucky's Ancient Sandstone

4 stops

Mist, Moonlight, and Mountain Gorges: A Couples' Escape to Daniel Boone National Forest

2 Days · Couples

Daniel Boone NF (Stearns, London), Kentucky

Mist, Moonlight, and Mountain Gorges: A Couples' Escape to Daniel Boone National Forest

5 stops

Frozen Niagara & Firefly Light: A Family Weekend in Mammoth Cave

2 Days · Young Families

Mammoth Cave area, Kentucky

Frozen Niagara & Firefly Light: A Family Weekend in Mammoth Cave

3 stops

Cool Stone, Slow Days: Three Nights at Mammoth Cave

3 Days · Active Retirees

Mammoth Cave area, Kentucky

Cool Stone, Slow Days: Three Nights at Mammoth Cave

4 stops

Frozen Niagara & Firefly Evenings: 2 Days at Mammoth Cave

2 Days · Young Families

Mammoth Cave area, Kentucky

Frozen Niagara & Firefly Evenings: 2 Days at Mammoth Cave

4 stops

Sandstone Arches & Small Legs: 2 Days in Red River Gorge

2 Days · Young Families

Red River Gorge (Slade area), Kentucky

Sandstone Arches & Small Legs: 2 Days in Red River Gorge

3 stops

Falls, Rails, and Gorges: A Gentle Three Days in Daniel Boone National Forest

3 Days · Active Retirees

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails, and Gorges: A Gentle Three Days in Daniel Boone National Forest

6 stops

Stone Arches & Slow Mornings: Two Days in the Red River Gorge

2 Days · Couples

Red River Gorge (Slade area), Kentucky

Stone Arches & Slow Mornings: Two Days in the Red River Gorge

4 stops

Mist, Moonlight & Mountain Rails: Two Days in Daniel Boone National Forest

2 Days · Couples

Daniel Boone NF (Stearns, London), Kentucky

Mist, Moonlight & Mountain Rails: Two Days in Daniel Boone National Forest

5 stops

Mist, Moonbows, and Mountain Rails: A Family Weekend in Daniel Boone National Forest

2 Days · Young Families

Daniel Boone NF (Stearns, London), Kentucky

Mist, Moonbows, and Mountain Rails: A Family Weekend in Daniel Boone National Forest

4 stops

Stone Arches & Slow Mornings: 3 Days in Red River Gorge

3 Days · Active Retirees

Red River Gorge (Slade area), Kentucky

Stone Arches & Slow Mornings: 3 Days in Red River Gorge

4 stops

Arches, Not Ambition: 3 Slow Days in Red River Gorge with Little Ones

3 Days · Young Families

Red River Gorge (Slade area), Kentucky

Arches, Not Ambition: 3 Slow Days in Red River Gorge with Little Ones

3 stops

Frozen Light & Limestone Silence: 3 Days in Mammoth Cave

3 Days · Couples

Mammoth Cave area, Kentucky

Frozen Light & Limestone Silence: 3 Days in Mammoth Cave

6 stops

Misty Falls & Ancient Gorges: 3 Days in Daniel Boone National Forest

3 Days · Couples

Daniel Boone NF (Stearns, London), Kentucky

Misty Falls & Ancient Gorges: 3 Days in Daniel Boone National Forest

5 stops

Misty Falls & Slow Rails: 3 Days in Daniel Boone National Forest with Little Ones

3 Days · Young Families

Daniel Boone NF (Stearns, London), Kentucky

Misty Falls & Slow Rails: 3 Days in Daniel Boone National Forest with Little Ones

6 stops

Frozen Waterfalls & Firefly Evenings: 3 Days in Mammoth Cave with Kids

3 Days · Young Families

Mammoth Cave area, Kentucky

Frozen Waterfalls & Firefly Evenings: 3 Days in Mammoth Cave with Kids

5 stops

Sandstone and Stillness: Three Days in Red River Gorge

3 Days · Couples

Red River Gorge (Slade area), Kentucky

Sandstone and Stillness: Three Days in Red River Gorge

5 stops

Underworld & Bluegrass Light: 3 Days at Mammoth Cave

3 Days · Couples

Mammoth Cave area, Kentucky

Underworld & Bluegrass Light: 3 Days at Mammoth Cave

4 stops

Bison, Stars & Slow Water: 3 Days in Land Between the Lakes

3 Days · Young Families

Land Between the Lakes (KY side), Kentucky

Bison, Stars & Slow Water: 3 Days in Land Between the Lakes

5 stops

Stone Arches & Quiet Fire: A Winter Escape to Red River Gorge

2 Days · Couples

Red River Gorge (Slade area), Kentucky

Stone Arches & Quiet Fire: A Winter Escape to Red River Gorge

4 stops

Arches, Firelight & Small Feet on Stone: 2 Days in Red River Gorge

2 Days · Young Families

Red River Gorge (Slade area), Kentucky

Arches, Firelight & Small Feet on Stone: 2 Days in Red River Gorge

3 stops

Stone Arches & Slow Mornings: 2 Days in Red River Gorge

2 Days · Active Retirees

Red River Gorge (Slade area), Kentucky

Stone Arches & Slow Mornings: 2 Days in Red River Gorge

3 stops

Waterfall Wonder & Rails: 3 Days in Daniel Boone National Forest with Kids

3 Days · Young Families

Daniel Boone NF (Stearns, London), Kentucky

Waterfall Wonder & Rails: 3 Days in Daniel Boone National Forest with Kids

4 stops

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

3 Days · Active Retirees

Paducah area, Kentucky

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

7 stops

Bluegrass Strings & River Light: Two Days in Owensboro

2 Days · Solo

Owensboro area, Kentucky

Bluegrass Strings & River Light: Two Days in Owensboro

6 stops

Slow River Days: A Family Wander Through Paducah

3 Days · Young Families

Paducah area, Kentucky

Slow River Days: A Family Wander Through Paducah

6 stops

Bourbon, Brick & River Light: 3 Days in Louisville for Two

3 Days · Couples

Louisville, Kentucky, Kentucky

Bourbon, Brick & River Light: 3 Days in Louisville for Two

11 stops

River Light & Quilted Streets: A Slow Paducah Weekend

3 Days · Couples

Paducah area, Kentucky

River Light & Quilted Streets: A Slow Paducah Weekend

6 stops

Where Three States Meet: A Gentle Passage Through Cumberland Gap

3 Days · Active Retirees

Cumberland Gap NHP, Kentucky

Where Three States Meet: A Gentle Passage Through Cumberland Gap

6 stops

Riverbank & Bluegrass: Three Slow Days in Owensboro

3 Days · Couples

Owensboro area, Kentucky

Riverbank & Bluegrass: Three Slow Days in Owensboro

9 stops

Falls, Rails, and Ridgelines: Three Unhurried Autumn Days in Daniel Boone National Forest

3 Days · Active Retirees

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails, and Ridgelines: Three Unhurried Autumn Days in Daniel Boone National Forest

6 stops

Frozen Niagara & Fall Light: Three Slow Days in Mammoth Cave

3 Days · Active Retirees

Mammoth Cave area, Kentucky

Frozen Niagara & Fall Light: Three Slow Days in Mammoth Cave

7 stops

Bourbon, Bats & Big Lawns: 3 Days in Louisville with Teens

3 Days · Teen Families

Louisville, Kentucky, Kentucky

Bourbon, Bats & Big Lawns: 3 Days in Louisville with Teens

9 stops

Prairie Light & Quiet Water: Three Days Between the Lakes

3 Days · Couples

Land Between the Lakes (KY side), Kentucky

Prairie Light & Quiet Water: Three Days Between the Lakes

5 stops

Falls, Rails & Firelight: 3 Days in Daniel Boone National Forest

3 Days · Teen Families

Daniel Boone NF (Stearns, London), Kentucky

Falls, Rails & Firelight: 3 Days in Daniel Boone National Forest

8 stops

Stone Arches & Winter Silence: 3 Days in Red River Gorge

3 Days · Couples

Red River Gorge (Slade area), Kentucky

Stone Arches & Winter Silence: 3 Days in Red River Gorge

5 stops

Showing 60 of 68 — explore all of Kentucky.

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