LEXINGTON WALKING TOUR FIELD GUIDE
Lipstick & Legends: A Three‑Hour Walking Dinner and Storytelling Circuit Through Downtown Lexington
A 3‑hour, 21+ walking experience that pairs four food stops and a final cocktail with stories celebrating Kentucky’s iconic women.
Lipstick & Legends: A Three‑Hour Walking Dinner and Storytelling Circuit Through Downtown Lexington.
Lipstick & Legends is an afternoon walking dinner party and storytelling experience in downtown Lexington that celebrates iconic Kentucky women — past and present — while guests enjoy savory bites and spirited conversation.
Highlights
Outing Highlights
Four savory stops and a final cocktail
The tour moves through downtown Lexington with four food tastings followed by a concluding cocktail, designed as a progressive, social dinner over the course of the outing.
Celebrating Kentucky’s legendary women
Guided storytelling weaves bold, surprising, and inspiring accounts of women who helped shape Lexington and the Commonwealth, delivered with heart and humor.
An afternoon dinner party with a touch of sparkle
Expect lively conversation, a festive atmosphere, and playful touches — come hungry, and bring red lipstick if you want to lean into the event’s encouraged style.
What the day feels like
What the afternoon feels like
Over three hours you’ll stroll through downtown Lexington, stopping at four curated food venues before finishing with a cocktail — along the way a guide shares lively stories about influential women from Kentucky, creating a blend of food, fellowship, and local history.
THE BITES
Four savory stops and a final cocktail
The tour moves through downtown Lexington with four food tastings followed by a concluding cocktail, designed as a progressive, social dinner over the course of the outing.
THE STORIES
Celebrating Kentucky’s legendary women
Guided storytelling weaves bold, surprising, and inspiring accounts of women who helped shape Lexington and the Commonwealth, delivered with heart and humor.
THE MOOD
An afternoon dinner party with a touch of sparkle
Expect lively conversation, a festive atmosphere, and playful touches — come hungry, and bring red lipstick if you want to lean into the event’s encouraged style.
Suitability
Who it's for
Who this tour suits — and who should look elsewhere.
Practical planner
Details to review before reserving
The experience runs for approximately 3 hours in the afternoon.
Come hungry; red lipstick is encouraged if you want to embrace the event’s playful dressup element.
Participants must be 21 years or older.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the tour?
The Lipstick & Legends tour lasts approximately 3 hours.
Is there an age requirement?
Yes — the experience is for guests 21 and over.
What does the tour include?
The tour includes four food stops and a final cocktail while guides share stories of iconic Kentucky women.
What should I bring or wear?
Come hungry; red lipstick is encouraged as a playful accessory for the event.
Is this a walking tour?
Yes — the experience involves strolling through downtown Lexington across multiple stops.
Who operates the tour?
The tour is operated by Bites of the Bluegrass.