Home Cover Story 2022 Lexington Staycation Summer Guide

2022 Lexington Staycation Summer Guide

Ace’s Annual Summer Guide is all about “Save the Date.” 

Lexington is such an embarrassment of riches in the summertime, it’s easy to lose track of what’s happening and when. 

Yes, we do all have 482,000 digital reminders at our literal fingertips all day everyday (and this Guide is available digitally as well), but sometimes you just want to see an entire Summer of options laid out in front of you!

Long before a pandemic entered the lexicon and kept everyone at home, Lexington has always been brimming with summer staycation options. 

Once again, the city is anything but sleepy this summer.

From live music to movie series and dozens of Fairs and Fests, Lexington has something for everyone, in every neighborhood, nearly every week this summer. 

*As always, times and dates are subject to change. Confirm with the venue.


JUN 15 Playthink Festival, Harrodsburg

JUN 25 Paint the Town, downtown Lex

JULY 8 Berea Craft Festival

JUL 16 Concours d’Elegance, Keeneland

JUL 16 GonzoFest, Louisville

AUG 6 Shaker Village Craft Fair

AUG 13 Picnic with the Pops (Motown), Keeneland

AUG 20 Woodland Art Fair 

SEP 10 Waveland Art Fair 

OCT 1 Wilmore Arts and Crafts Festival 


Lexington’s 10th annual downtown plein air painting extravaganza, Paint the Town, is Saturday June 25, 2022. Artists will spend the day painting cityscapes throughout downtown Lexington.


The 2022 Concours d’Elegance at Keeneland will feature Porsche as this year’s featured marque and will include four classes, Air Cooled, Water Cooled, “356” and Race Car.


JUN 11 Beer Cheese Festival, Winchester

JUN 18 Kentucky Wine and Vine Fest, Nicholasville

JUN 20 SoulFeast Week, Lexington

JUN 25 the 25th Annual Ashland Lawn Party, Ashland Henry Clay Estate

JUL 16 Sweet Corn Festival, Georgetown

JULY 21-31 Lexington Restaurant Week 

JUL 23 Hops and Vine Craft Beer and Wine Festival, Richmond

SEP 2 Kentucky State BBQ Festival, Danville

SEP 8 Fireman’s Chili Kickoff, Georgetown 

SEP 14 Kentucky Bourbon Festival, Bardstown 

SEP 15 Bourbon and Beyond, Louisville

SoulFeast Week is a traditional food week featuring black-owned restaurants in Lexington, Kentucky. Participating restaurants will create a unique, off-menu food entree for $10. In partnership with Black Soil KY, each food entree must feature at least one ingredient sourced from a black farmer or producer in Kentucky. June 20 through June 26 at participating restaurants.


JUN 4 Southland Street Fair

JUN 9 Bluegrass Fair begins

JUN 11 Francisco’s Farm Art Fair, Midway 

JUN 25 Lexington Pride Festival

JUL 4 Lexington’s July 4th Festival

AUG 13 Small Town America Festival, Mt. Sterling

SEP 9 Roots and Heritage Festival

SEP 9 Festival of the Horse, Georgetown 

SEP 17 Midway Fall Festival


JUN 12 Hartland Tour of Homes 

JUL 31 Bluegrass Iris Society’s Annual Iris Sale, Lexington Green

AUG 27 Tour of Remodeled Homes

SEP-OCT Grand Tour of Homes


JUN 5 Polo practices and matches begin, KY Horse Park 

JUL 11 Lexington’s Junior League Horse Show begins, KY Horse Park

Lexington Junior League Horse Show

JUL 15 Breyerfest, KY Horse Park 

JUL 30 Hats off to Kentucky Horses Day, KY Horse Park

JUL 31 Live Racing, Red Mile (thru Oct 9)

SEP 2 KHP Foundation Battle in the Saddle, KY Horse Park 

SEP 9 Festival of the Horse, Georgetown 

SEP 12 Keeneland’s September Yearling Sales begin

OCT 7 Keeneland Fall Meet begins

OCT 26 National Horse Show, KY Horse Park 

NOV 4 Breeders Cup, Keeneland

Weather permitting, Polo public matches are held between June 1st through the end of September at the Kentucky Horse Park. Practices take place Wednesdays/Fridays at 5:30 PM and matches at 3 pm on Sundays. 



Big Band & Jazz is Lexington’s longest running and outdoor concert series held weekly from 7-8:30 pm at Moondance in June and Ecton Park in July.

Moondance Amphitheater

JUN 7 DiMartino/Osland Jazz Orchestra

JUN 14 Walnut Street Ramblers

JUN 21 Brass Impact

JUN 28 Lexington Summer Concert Band

Ecton Park

JUL 5 Miles Osland Little Big Band w/ Vince DiMartino

JUL 12 Brett Evans Trombone Jazz Ensemble

JUL 19 Ozmosis

JUL 26 Tim Lake and the Blue Jazz Persuaders

AUG 2 Uncle Sam’s Bait Shop

AUG 9 Osland/Dailey Jazztet


June’s Northside Nights concerts are Thursdays at 6:30  pm on the lawn of the Loudon House at Castlewood Park.

JUN 10 The Positive Movement Band

JUN 24 Special Sessions

JUL 8 Benny J & Friends

JUL 22 Elite 7 Band

AUG 5 1SoundBand

AUG 19 The Tim Talbert Project

SEP 2 Rhythm & Soul

Southland Jamboree at Beaumont Center’s Moondance Amphitheatre are on Thursdays at 7 pm.

JUN 2 Jim Hurst Bluegrass Band

JUN 9 Fast Track

JUN 16 Blue Eagle Band

JUN 23 Custom Made Bluegrass

JUN 30 Wolfpen Branch

JUL 7 Maddie Murray and Darren Wasson Band

JUL 14 Hammertowne

JUL 21 Cane Run Bluegrass

JUL 28 Alan Bibey & Grasstowne

AUG 4 Olde Towne Project

AUG 11 Don Rigsby

AUG 18 Ida Clare

AUG 25 New Coon Creek Girls Reunion

SEP 1 Fenced In

Summer Nights in Suburbia are at Moondance Amphitheater, 7 pm. 

JUN 3 DJ Rice Band

JUN 17 Lauren Mink Band

JUL 1 Bedford Band

JUL 15 Brother Smith

JUL 29 Honeychild

AUG 12 DeeOhGee



Central Bank Thursday Night Live returns to Fifth Third Bank Pavilion in downtown Lexington on Thursday evenings from 5-8 pm.

JUN 2 Five Below Band

JUN 9 Paul Childers

JUN 16 The Johnson Brothers

JUN 23 64West

JUN 30 Eagles Tribute Band

JUL 7 Honeychild

JUL 14 The Ranahans

JUL 21 Boogie G & The Titanics

JUL 28 Encore of Lexington

AUG 4 The Big Maracas

AUG 11 Tim Talbert Project

AUG 18 The Twiggenburys

AUG 25 Kenny Owens & Group Therapy

SEP 1 Mercy Men

SEP 8 The Binders

SEP 15 Canvas

SEP 22 Rebel Without A Cause

SEP 29 Superfecta

OCT 6 Mojo Tones


JUN 2 The Great American Brass Band Festival, Danville

JUN 3 Kentucky R&B Fest, KFC Yum (Louisville)

JUN 21 The Chicks Tour, Riverbend (Cinci)

JUN 23 Kenny Chesney, Riverbend (Cinci)

JUN 26 New Kids on the Block, Rupp Arena

JUL 12 Rod Stewart, Riverbend (Cinci)

JUL 14 The Cult, Riverbend (Cinci)

JUL 15 Master Musicians Festival, Somerset

JUL 21 Jimmy Buffett, Riverbend (Cinci)

JUL 23 Steve Earle and the Dukes, The Burl

JUL 30 Outlaw Music Festival, Riverbend (Cinci)

AUG 25 Jason Aldean, Riverbend (Cinci)

SEP 3 The Black Keys, Riverbend (Cinci)

SEP 6 Backstreet Boys, Rupp Arena

SEP 9 Alan Jackson, Rupp

SEP 15-18 Bourbon & Beyond, Louisville

SEP 17 Kentucky Heritage Jazz Festival, Harrodsburg 

SEP 22-25 Louder than Life, Louisville

Railbird Festival is sitting out 2022, and will return in 2023 with a new location at Red Mile. 


Free Friday Flicks at Jacobson Park

Friday Flicks offers an evening of activities and a movie beginning Fridays in June. Movies don’t start til dusk.

JUN 3 Raya and the Last Dragon

JUN 10 Willy Wonka and the Chocolate Factory

JUN 17 Sing 2

JUN 24 Encanto 

Hollywood Classics

The Hollywood Classics series returns to the Kentucky Theatre this summer after a pandemic-paused hiatus. 

JUN 1 Roman Holiday, 1953

JUN 8 Star Wars, 1977

JUN 15 A Patch of Blue, 1965

JUN 22 Goldfinger, 1964

JUN 29 2001: A Space Odyssey, 1968

JUL 6 The Big Sleep, 1946

JUL 13 An American Werewolf in London, 1981

JUL 20 Sleeping Beauty, 1959

JUL 27 Bonnie and Clyde, 1967

AUG 3 Stand By Me, 1986

AUG 10 The Man Who Knew Too Much, 1956

AUG 17 West Side Story, 1961

AUG 24 Shakespeare in Love, 1998

AUG 31 The Godfather, 1972

SEP 7 The Big Lebowski, 1998

Harry Dean Stanton Fest 

Lexington’s Harry Dean Stanton Fest is July 15 – 17 and will feature special guest Allison Anders. Before she directed American independent classics like GAS FOOD LODGING and MI VIDA LOCA, one of Anders’ first film jobs was on the set of Paris, Texas where a right place/right time encounter with Harry Dean Stanton helped him connect to the character of Travis and helped her unlock her talent in working with actors. It was the beginning of a beautiful friendship. 


JUN 4 Run for the Nun 5k, St. Elizabeth Ann Seton

JUN 11 Donut Dash 3k

JUN 18 Wild Hearts Superhero 5k

JUL 4 Bluegrass 10,000

AUG 13 Midsummer Night’s Run 5kgroup of people running

AUG 20 DV8K Life Changing Run

AUG 26 Cupcake Classic 3k

SEP 30 Bourbon Chase Relay 


JUL 7 PGA Barbasol Championship (thru Jul 11), Nicholasville

AUG 1 Lexington Challenger Tennis Tourney, Boone Tennis Complex