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Lexington, Kentucky Summer Guide 2021: Fests, Music, Movies and More


Did someone say staycation?

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.




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.

At Moondance Ampitheater

JUN 1       DiMartino, Osland Little Big Band

JUN 8       Marlin McKay Quintet

JUN 15     Tim Lake and the Jazz Blues Persuaders

JUN 22     Ross Whitaker Jazz Trio

JUN 29     Lexington Summer Concert Band *patriotic concert*

JUL 2       The Metrognomes *patriotic concert, special Friday show*

At Ecton Park

JUL 6       Dan Brock & Friends

JUL 13     Walnut Street Ramblers

JUL 20     Osland/Dailey Jazztet

JUL 27     Ozone

AUG 3      Brass Impact

AUG 10    DiMartino/Osland Jazz Orchestra (DOJO)

AUG 17    Young at Heart Big Band


The Front Porch Jazz series at the Isaac Murphy Memorial Art Garden on the corner of 3rd St. and Midland Ave.

JUL 10    From the Front Porch Jazz, 6 pm

AUG 28   From the Front Porch Jazz 


June’s new Northside Nights concerts are Thursdays at 7 pm on the lawn of the Loudoun House at Castlewood Park.

JUN 3      Seven Shades of Soul

JUN 10    Rae Camp Band

JUN 17    Band New

JUN 24    Miss Tina Fondren & Big Chill

July’s Northside Nights concerts are Thursdays at 7 pm at Douglass Park.

JUL 1        Tim Talbert Project

JUL 8        Honeychild

JUL 15      Benny J & Friends

JUL 29      One Sound Band


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

JUN 17    Kenny and Amanda Smith      

JUN 24    Ida Clare

JUL 8       Alan Bibey and Grasstowne

JUL 15     Blind Ricky

JUL 22     Hammertowne

AUG 19    Custom Made Bluegrass    

AUG 26    Blue Eagle Band 

SEP 16     Fenced In    

SEP 23     Kentucky Wild Horse


The Springhouse Music Series at Castle & Key Distillery on the first Wednesday of the month from June through October. Gates open at 5 pm, live music at 6 pm.

JUL 7       Brett Higgins & Donnie Bowling

AUG 4      Lauren Mink

SEP 1       Jordan English

OCT 6       TBA


Summer Nights in Suburbia at Moondance Amphitheater. Gates open at 5:30 pm, show is from 7 – 9 pm.

JUN 25    Second Hand News

JUL 23    The Other Brothers

AUG 27   Honeychild

SEP 24    C the Beat


Each Tahlsound Music Festival event is the fourth Sunday of each month from April through September, held in the parking lot of a business on Southland at 5 pm.

JUN 27     The Wooks, Oleika Temple Great Lawn on Southland Drive

JUL 25      Johnson Brothers & The Bats, Oleika Temple Great Lawn on Southland Drive

AUG 22     Ben Sollee, Oleika Temple Great Lawn on Southland Drive


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

JUL 1             Nightflyer: The Ultimate Eagles Tribute Band

JUL 8             Sixtyfourwest – Bill & Aaron

JUL 15           The Tim Talbert Project

JUL 22           Lauren Mink

JUL 29           Paul Childers

AUG 5            The Big Maracas

AUG 12          The Ranahans

AUG 19          Honeychild

AUG 26          Kenny Owens & Group Therapy

SEP 2             Mercy Men

SEP 9             Five Below Band

SEP 16           The Twiggenburys

SEP 23           The Johnson Brothers

SEP 30           Rebel Without A Cause

OCT 7             Kimberly Carter & Carrying On


JUL 31      Riders in the Sky, 7 pm

SEP 8        John McEuen and the Mclain Family Band, 6:30 pm


WoodSongs Old-Time Radio Hour returns to the Lyric Theatre in August. Mondays at 6:45 pm, watch live-as-it-happens via Woodssongs YouTube Channel.

AUG 16       Rhonda Vincent and the Rage


The inaugural Midway Music Festival: Off the Rails is on Saturday, July 24.

Railbird Festival returns to Keeneland for its second festival on Saturday, August 28 and Sunday, August 29.



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

JUN 4       Frozen 2

JUN 11     The Croods 2

JUN 18     Trolls World Tour

JUN 25     Iron Giant


THU JUN 3     The first official funnelcake of the season must traditionally be consumed at the St. Elizabeth Ann Seton Country Fair

THU JUN 10    The Bluegrass Fair is June 10 through June 20 at Masterson Station Park. Gates open 5 pm on weekdays & 3 pm on weekends

SAT JUN 12    Francisco’s Farm Art Fair in Midway, 10 am 

SUN JUN 13    Francisco’s Farm Art Fair in Midway, 10 am 

CANCELED: Festival of the Bluegrass 2021

JUL 3    There’s no Fourth of July Festival and Parade this year but Lexington’s Fourth of July celebration for this year includes fireworks at 10 pm and a twist on the Patriotic Concert

JUL 9-11   Berea Craft Festival in downtown Berea. Friday/Saturday 10am-6pm; Sunday 10am-5pm

JUL 16-18  BreyerFest 2021 (virtual event, no in-person event/activities at Kentucky Horse Park)

JUL 17    Keeneland Concours d’Elegance, 9 am – 4:30 pm

JUL 18        Diamond Rings & Pretty Things Wedding Show, 11am-4pm, Central Bank Center

JUL 24         Hops & Vine Festival, 2-10 pm, downtown Richmond, KY

AUG 14         Small Town America Festival, 10 am, Mt. Sterling

AUG 20-22     Natural Bridge Artisan Festival

AUG 21 & 22   Woodland Art Fair, Woodland Park

SEP 10-12    Festival of the Horse, downtown Georgetown. Fri 4pm‑10pm; Sat 11am‑10pm, Sun 11am‑5pm

SEP 11-12    Waveland Art Fair, Sat 10am-5pm; Sun 11am-5 pm

SEP 25          Phoenix Festival

SEP 26          Southland Street Fair, Southland Drive



The perennially popular Down to Earth Plant sale hosted in May by the Down to Earth Garden Club at the Woodland Christian Church, was CANCELED for 2021 and hopes to return in May of 2022


CANCELED: Kenwick Bungalow Tour

JUN 3   Lexington’s Chapter of Wild Ones presents Hummingbirds at Pollinators, 6:30 pm, St. Michael’s Church at Bellefonte

JUN 22    Fayette County Extension Office Gardening Workshops hosts Fall Blooming Perennials. Check ahead to see if the workshop is virtual or in-person. Visit fayette.ca.uky.edu and click the “Upcoming Events” tab

JUN 26 AND JUN 27   For the 2021 Open Gates to Bluegrass Living Garden Tour, Lexington Council Garden Clubs will host a self-guided tour of eight carefully curated Lexington gardens. This year’s participants include gardens on Sallee Drive, Meadowbrook Drive, Blenheim Drive, Kingsway, Hart Road, and Walton Avenue. Attendees may also tour the community garden at Ashland Terrace, located at 475 S. Ashland Ave. 1-5 pm both days

JULY 31  The Bluegrass Iris Society hosts their annual club fundraiser Iris Sale, 10 am, the lower level of Lexington Green (They always sell out early. Trust us.) 

AUG 5    Wild Ones Picnic, 6:30 pm, Unitarian Universalist Church at 3564 Clays Mill Road


JUN 26    Paint the Town 2021. Artists will spend the day painting cityscapes throughout downtown Lexington

JUN 27 – JUL 17    Kentucky Performing Arts announced Governor’s School for the Arts (GSA) returns to in-person and traditional instruction at the University of Kentucky this summer

AUG 3-8    Ballet Under the Stars, Woodland Park

AUG 14   Picnic with the Pops

SEP 16-19   An abbreviated version of the typical 10-day Chamber Music Festival of Lexington returns 


JUN 5       Lexington Humane Society’s Mutt Strut, 8 am, Keeneland

JUN 5       North Lime Donut Dash 3K, 8 am, Wellington Park

JUN 12     Run for the Nun, 8 am, St. Elizabeth Ann Seton

JUN 19 – 27   The Hundred Acre 5K (virtual)

JUN 19     Wild Hearts Fun Run Superhero 5K & 10K, 8 am, Keeneland

JUN 26     No Greater Honor 5K, 8 am, Keeneland 

JUN 26     RJ Corman 5K, 8 am, Wilmore downtown

JUL 2-4     Virtual Great Buffalo Chase 5K

JUL 3        Bluegrass 10,000, 8 am, downtown Lexington

JUL 9        Distillery Dash 5k/10k, 7 pm, Masterson Station Park

JUL 16     Crank & Boom Sprint for Scoops 3K, 7:30 pm, Wellington Park

JUL 16-18   BreyerFest 5K Virtual Run/Walk

JUL 24      Christmas in July 6K, 8 am, Coldstream Research Park

JUL 24      Shepherd’s House Run For Recovery, 8 am, Keeneland

JUL 30      Radler Rush Cross Country 5k/10k, 7 pm, Masterson Station Park

AUG 14     Midsummer Night’s Run, 7:30 pm, downtown Lexington

AUG 21     DV8K Life Changing Run, 8 am, Keeneland

AUG 22     Kids Triathlon, 7:30 am, Beaumont YMCA

AUG 27     Cabernet Canter Cross Country 5k/10k, 7 pm, Talon Winery

AUG 27     Cupcake Classic 3K, 7:30pm, Wellington Park


MAY 29    Aquatic Centers at Southland, Tates Creek, Woodland, and Castlewood open

JUN 5       Pools at Shillito and Douglass open

The spraygrounds at Masterson Station Park and Jacobson Park are already open daily, and the Jacobson boat dock is open on the weekends


THU JUN 17 – SUN JUN 27     SoulFest Week

THU JUL 22 – SUN AUG 1    Lexington Restaurant Week 

SAT AUG 7        Kentucky Wine & Vine Festival, 1-9 pm, Nicholasville


JUL 1, 15, 22    Thirsty Thursdays + Bark in the Park, Lexington Legends, 6 pm

JUL 12-17        Lexington Junior League Charity Horse Show, Kentucky Horse Park

JUL 15-18        Barbasol Championships, Keene Trace

AUG 5               Thirsty Thursdays + Bark in the Park, Lexington Legends, 6 pm

SEP 2, 9, 23, 30  Thirsty Thursdays + Bark in the Park, Lexington Legends, 6 pm



This summer guide also appears on page 8, 9, and 10 of the June 2021 print edition of ace magazine.

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