Date Night Ideas in Winchester, KY

Romantic date night ideas in Winchester, KY. Restaurants, shows, concerts, and unique experiences for couples.

50 results found

Things to Do This Weekend Today Kid-Friendly Free Events Outdoors Concerts & Live Music Food & Dining Fitness & Sports Arts & Culture

Photo by Mike Petrucci on Unsplash — representative image for Painting Watercolor Horses

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Painting Watercolor Horses

Tue, Apr 14, 2:00 PM–4:00 PM UTC · Scott County Public Library · 104 South Bradford Ln, Georgetown, KY · Ages 18+

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Photo by Declan Sun on Unsplash — representative image for Shred It! In the Library Parking Lot

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Free

Shred It! In the Library Parking Lot

In 4 days · Sat, Apr 18, 2:00 PM–5:00 PM UTC · Scott County Public Library · 104 South Bradford Ln, Georgetown, KY

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Bluegrass Heritage Museum

Bluegrass Heritage Museum · 217 South Main Street, Winchester, KY

Museum Exhibit in Winchester, KY

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Photo by Tasha Kostyuk on Unsplash — representative image for Learn How to Play Mahjong, Part 3

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Learn How to Play Mahjong, Part 3

In 2 days · Thu, Apr 16, 9:30 PM–11:30 PM UTC · Scott County Public Library · 104 South Bradford Ln, Georgetown, KY

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OVG Concert Series: Dwight Yoakam & ZZ Top: Dos Amigos Tour

In 6 days · Sun, Apr 19, 11:00 PM–3:59 AM UTC · Gatton Park on the Town Branch · 795 Manchester Street, Lexington, KY

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Photo by Anna Blake on Unsplash — representative image for Lower Howard's Creek Nature Preserve

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Lower Howard's Creek Nature Preserve

Lower Howard's Creek Nature Preserve · 457 South Maple, Winchester, KY

Outdoor Space in Winchester, KY

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Tim Meadows at Comedy Off Broadway

In 2 days · Apr 16 – Apr 19 · Comedy Off Broadway · 161 Lexington Green Circle, Lexington, KY

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World Ballet Company: Swan Lake

In 6 days · Sun, Apr 19, 10:00 PM–3:59 AM UTC · Lexington Opera House · 401 West Short Street, Lexington, KY

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Photo by Wes Hicks on Unsplash — representative image for Harkness Edwards Vineyards

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Harkness Edwards Vineyards

Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

General in Winchester, KY

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Photo by Samuel Regan-Asante on Unsplash — representative image for Raíces: The Making of Latino Legacies in Racing

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Raíces: The Making of Latino Legacies in Racing

Happening now · Jan 27 – Nov 14 · Keeneland Library · 4201 Versailles Road, Lexington, KY

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Photo by Kyle Bushnell on Unsplash — representative image for Classical Music Sunday

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Classical Music Sunday

In 5 days · Sun, Apr 19, 6:30 PM–7:30 PM UTC · Central Library · 140 E Main St, Lexington, KY 40507, Lexington, KY

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Photo by Roberto Nickson on Unsplash — representative image for Regeneration Distilling Co

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Outdoor

Regeneration Distilling Co

Regeneration Distilling Co · 31 E Broadway, Winchester, KY

General in Winchester, KY

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Photo by Diego Costa on Unsplash — representative image for Southland Jamboree

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Southland Jamboree

In 3 days · Thu, Apr 16, 11:00 PM–12:30 AM UTC · Central Library · 140 E Main St, Lexington, KY 40507, Lexington, KY

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Photo by WISS Shanghai on Unsplash — representative image for Hooked on Books

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Hooked on Books

In 4 days · Sat, Apr 18, 7:00 PM–8:00 PM UTC · Beaumont Branch · 3080 Fieldstone Way, Lexington, KY 40513, Lexington, KY

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Photo by Meritt Thomas on Unsplash — representative image for Abettor Brewing

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Outdoor

Abettor Brewing

Abettor Brewing · 128 N Highland St, Winchester, KY

General in Winchester, KY

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Photo by Centre for Ageing Better on Unsplash — representative image for Seed Library

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Seed Library

Happening now · Apr 6 – May 24 · Scott County Public Library · 104 South Bradford Ln, Georgetown, KY

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The Lexington Antique Show at Athens

Happening now · Apr 5 – Dec 7 · Athens Schoolhouse · 6270 Athens-Walnut Hill Pike, Lexington, KY

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Photo by Ashley Owen on Unsplash — representative image for Ale-8-One Bottling Company

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Ale-8-One Bottling Company

Ale-8-One Bottling Company · 25 Carol Road, Winchester, KY

General in Winchester, KY

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Spring Wildflower Hike

Happening now · Mar 25 – Apr 16 · Boone Creek Outdoors · 8291 Old Richmond Road, Lexington, KY

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Spring Birding Hike

Happening now · Mar 26 – Apr 17 · Boone Creek Outdoors · 8291 Old Richmond Road, Lexington, KY

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Photo by Matt & Chris Pua on Unsplash — representative image for Main Event Lexington

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Outdoor

Main Event Lexington

Main Event Lexington · 240 Canary Road, Lexington, KY

Arcade Games in Lexington, KY

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Photo by Getty Images on Unsplash — representative image for Discover! Endangered Species

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Discover! Endangered Species

In 2 days · Thu, Apr 16, 6:00 PM–7:00 PM UTC · Scott County Public Library · 104 South Bradford Ln, Georgetown, KY

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Lexington Sporting Club vs Tampa Bay Sun FC

In 4 days · Apr 18 – Apr 19 · Lexington Sporting Club Stadium · 250 Doe Run Trail, Lexington, KY

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Photo by Edwin Petrus on Unsplash — representative image for Kentucky Doll and Toy Museum

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Kentucky Doll and Toy Museum

Kentucky Doll and Toy Museum · 106 West Main Street, Carlisle, KY

Museum Exhibit in Carlisle, KY

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Thursday Night Live at The Fifth Third Pavilion

Happening now · Apr 2 – Oct 10 · Pride of Place Walking Tour · Lexington, Lexington, KY

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Pinocchio Performance

In 4 days · Apr 18 – Apr 20 · Lexington Children's Theatre · 418 West Short Street, Lexington, KY

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Photo by Vitaly Gariev on Unsplash — representative image for Living Arts & Science Center

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Outdoor

Living Arts & Science Center

Living Arts & Science Center · 362 North Martin Luther King, Lexington, KY

Stem Tech in Lexington, KY

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Keeneland Racing Spring Meet

Happening now · Apr 1 – Apr 26 · Keeneland Racecourse · 4201 Versailles Road, Lexington, KY

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Photo by Geert Pieters on Unsplash — representative image for Lisa Low reading/workshop

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Lisa Low reading/workshop

In 4 days · Sat, Apr 18, 6:00 PM–7:30 PM UTC · Eastside Branch · 3000 Woodhill Dr, Lexington, KY 40509, Lexington, KY

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Photo by Eliézer Fernandes on Unsplash — representative image for Central Bank Center and Rupp Arena

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Central Bank Center and Rupp Arena

Central Bank Center and Rupp Arena · 425 W. High Street, Lexington, KY

Sports Fitness in Lexington, KY

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Photo by Elijah Ekdahl on Unsplash — representative image for Live Music with Jeff Blackburn and Steve Maynard

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Live Music with Jeff Blackburn and Steve Maynard

Jun 14 – Aug 31 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Inna Safa on Unsplash — representative image for Live Music with Lauren Mink and Dale Adams

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Live Music with Lauren Mink and Dale Adams

Jun 21 – Sep 21 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Taylor Heery on Unsplash — representative image for Ashland, The Henry Clay Estate

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Ashland, The Henry Clay Estate

Ashland, The Henry Clay Estate · 120 Sycamore Road, Lexington, KY

Arts Crafts in Lexington, KY

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Photo by Jacob McGowin on Unsplash — representative image for Live Music with Meg Allen

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Live Music with Meg Allen

Jun 7 – Jun 8 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Piyanshu Sharma on Unsplash — representative image for Live Music with Casey Hensley

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Live Music with Casey Hensley

In 4 weeks · May 10 – May 11 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Дегтярев Николаевич on Unsplash — representative image for Nannine Clay Wallis Arboretum

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Outdoor

Nannine Clay Wallis Arboretum

Nannine Clay Wallis Arboretum · 616 Pleasant Street, Paris, KY

Outdoor Space in Paris, KY

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Photo by Jacob McGowin on Unsplash — representative image for Live Music with Erin Sliney

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Live Music with Erin Sliney

Jun 28 – Sep 14 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Jacob McGowin on Unsplash — representative image for Live Music with Bryant Carter

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Live Music with Bryant Carter

Sep 27 – Sep 28 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Hossein Nasr on Unsplash — representative image for Lyric Theatre and Cultural Arts Center

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Lyric Theatre and Cultural Arts Center

Lyric Theatre and Cultural Arts Center · 300 East Third Street, Lexington, KY

Theater in Lexington, KY

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Photo by Inna Safa on Unsplash — representative image for Live Music with Kristin Riley

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Live Music with Kristin Riley

Sep 6 – Sep 7 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Pramod Tiwari on Unsplash — representative image for Live Music with Kevin Cruise

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Live Music with Kevin Cruise

May 24 – Jul 27 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Adhitya Sibikumar on Unsplash — representative image for Cocktails + Bites Food & History Tour

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Cocktails + Bites Food & History Tour

Cocktails + Bites Food & History Tour · 215 W Main St, Lexington, KY

Food Drink in Lexington, KY

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Photo by Leon Rockel on Unsplash — representative image for Live Music with Chris Carpenter

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Free

Live Music with Chris Carpenter

May 17 – Aug 24 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Kyle Bushnell on Unsplash — representative image for Live Music with The Quilla Rose

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Live Music with The Quilla Rose

May 31 – Aug 10 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Alex Bracken on Unsplash — representative image for University of Kentucky Art Museum

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University of Kentucky Art Museum

University of Kentucky Art Museum · 405 Rose Street, Lexington, KY

Museum Exhibit in Lexington, KY

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Photo by Toni Cuenca on Unsplash — representative image for Mother's Day at The Vineyard

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Mother's Day at The Vineyard

In 4 weeks · May 10 – May 11 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by K8 on Unsplash — representative image for Harvest Moon Party

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Harvest Moon Party

Sep 25 – Sep 27 · Harkness Edwards Vineyards · 5199 Combs Ferry Road, Winchester, KY

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Photo by Edwin Petrus on Unsplash — representative image for American Saddlebred Museum

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Outdoor

American Saddlebred Museum

American Saddlebred Museum · 4083 Wing Commander Way, Lexington, KY

Museum Exhibit in Lexington, KY

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Photo by Vitaly Gariev on Unsplash — representative image for Intermediate ESOL - Culture & Conversation

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Free

Intermediate ESOL - Culture & Conversation

Mon, Dec 21, 10:30 PM–11:30 PM UTC · Northside Branch · 1733 Russell Cave Rd, Lexington, KY 40505, Lexington, KY

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Photo by Jonny Gios on Unsplash — representative image for Eastside Book Club

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Eastside Book Club

Tue, Aug 4, 9:30 PM–10:30 PM UTC · Eastside Branch · 3000 Woodhill Dr, Lexington, KY 40509, Lexington, KY

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View all cities in Kentucky →

Date Night Ideas in Winchester, KY

Painting Watercolor Horses

Shred It! In the Library Parking Lot

Bluegrass Heritage Museum

Learn How to Play Mahjong, Part 3

OVG Concert Series: Dwight Yoakam & ZZ Top: Dos Amigos Tour

Lower Howard's Creek Nature Preserve

Tim Meadows at Comedy Off Broadway

World Ballet Company: Swan Lake

Harkness Edwards Vineyards

Raíces: The Making of Latino Legacies in Racing

Classical Music Sunday

Regeneration Distilling Co

Southland Jamboree

Hooked on Books

Abettor Brewing

Seed Library

The Lexington Antique Show at Athens

Ale-8-One Bottling Company

Spring Wildflower Hike

Spring Birding Hike

Main Event Lexington

Discover! Endangered Species

Lexington Sporting Club vs Tampa Bay Sun FC

Kentucky Doll and Toy Museum

Thursday Night Live at The Fifth Third Pavilion

Pinocchio Performance

Living Arts & Science Center

Keeneland Racing Spring Meet

Lisa Low reading/workshop

Central Bank Center and Rupp Arena

Live Music with Jeff Blackburn and Steve Maynard

Live Music with Lauren Mink and Dale Adams

Ashland, The Henry Clay Estate

Live Music with Meg Allen

Live Music with Casey Hensley

Nannine Clay Wallis Arboretum

Live Music with Erin Sliney

Live Music with Bryant Carter

Lyric Theatre and Cultural Arts Center

Live Music with Kristin Riley

Live Music with Kevin Cruise

Cocktails + Bites Food & History Tour

Live Music with Chris Carpenter

Live Music with The Quilla Rose

University of Kentucky Art Museum

Mother's Day at The Vineyard

Harvest Moon Party

American Saddlebred Museum

Intermediate ESOL - Culture & Conversation

Eastside Book Club

Explore More in Winchester, KY

Date Night in Nearby Cities

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