2026 Summer Fun Guide

Lexington has long been rich with options when it comes to summer entertainment! We’ve put together a comprehensive list of the best summer festivals, concert series and other fabulous cultural events taking place over the next few months.

2026 Recurring Series

A look at various live music, film, theater and other recurring series taking place regularly throughout the warm weather months.  

Big Band & Jazz Series

Tuesdays through Aug. 11, 7-8:30 p.m. • Moondance Amphitheater (through June 30) and Ecton Park (July 7-Aug. 11) • lexingtonky.gov/playing/arts-events/big-band-jazz 

One of Lexington’s longest-running and most beloved concert series returns with a full schedule of free weekly big band and jazz music at Moondance Amphitheater and Ecton Park. Patrons are encouraged to bring a lawn chair or blanket for seating; picnics are also encouraged.

Moondance Amphitheater Schedule:

• June 2: Marlin McKay 12-Piece Big Band
• June 9: Somerset Big Band
• June 16: Lee Carroll Quintet
• June 23: Zach Brock
• June 30: Patriotic Big Band & Jazz: The Lexington Concert Band

Ecton Park Schedule

• July 7: DOJO-DiMartino/Osland Jazz Orchastra
• July 14: Brett Evans Trombone Orchestra
• July 21: Bryson Dunsmore Trio with Kirby Davis
• July 28: Walnut Street Ramblers
• Aug. 4: Miles Osland Little Big Band
• Aug. 11: RPM Quintet

Central Bank Thursday Night Live

Thursdays through Oct. 8, 5-8 p.m.  • Fifth Third Bank Pavilion at Henry A. Tandy Centennial Park, 251 W. Main Street • downtownlex.com/central-bank-thursday-night-live

Central Bank Thursday Night Live is a free, weekly outdoor event featuring live music from local and regional bands, food and beverage vendors and more. Taking place downtown under the Fifth Third Bank Pavilion, the event is held rain or shine, with hundreds of attendees gathering each month.

The summer schedule is below. Visit the event website for the full season line-up and additional details.   

2026 Summer Schedule:

• June 4 – Vinyl Richie
• June 11 – Binders Disco Revolution
• June 18 – TBA
• June 25 – The Ranahans 
• July 2 – Rewind Band
• July 9 – Vanguard Band
• July 16 – Superfecta 
• July 23 – Tahlsound Reggae Night
• July 30 – Dead Air Dennis & Bryan Himes Experience 
• Aug. 6 – TBA
• Aug. 13 – One More Round
• Aug. 20 – Mercy Men 
• Aug. 27 – Kenny Owners & Group Therapy 

Eastside Evenings

July 17-Aug. 28, 6-8 p.m. • Charles Young Park, 215 Midland Ave. • lexingtonky.gov/playing/arts-events/east-end-evenings 

This outdoor concert series brings live music to Lexington’s Eastside neighborhood. Attendees are encouraged to bring lawn chairs and blankets for seating while enjoying live R&B, soul, funk, and dance music.  

2026 Schedule:

• July 17 – Boogie G & the Titanics
• July 31 – VSP Band
• Aug. 14 – Benny J & Friends
• Aug. 28 – Honeychild 

Free Friday Flicks

Fridays in June, activities start at 7 p.m. and the movie starts at dark • Jacobson Park, 4001 Athens-Boonesboro Road • lexingtonky.gov/playing/arts-events/friday-flicks  

This outdoor summer film series features vendors and activities for all ages before the screening of a family-friendly film. Attendees are encouraged to bring lawn chairs or blankets for seating. 

2026 Film Schedule:

• June 5 – “Cars”
• June 12 – “G.O.A.T.”
• June 26 – “Hoppers” 

From the Front Porch Concert Series

June 27, July 25, Aug. 29, Sept. 26, 6-8 p.m. • Isaac Murphy Memorial Art Garden, 577 E. Third St.  • lexingtonky.gov/playing/arts-events/front-porch-concert-series 

Presented by Lexington Parks & Recreation and Phoenix Rising Lex, an organization dedicated to preserving, promoting and honoring the contributions of African Americans to the Bluegrass region’s equestrian history, this free summer jazz series takes place at the footprint of the home where Black jockey Isaac Murphy — considered by many to be the greatest jockey of all time — lived with his wife, Lucy, in the late 1800s. Attendees are encouraged to bring blankets or chairs and a picnic or grab dinner from a food truck on site. Performers were TBA at time of publication but will be posted online upon confirming.

Pioneer Playhouse

Tues.-Sat., June 6-Aug. 15 • Dinner at 7 p.m. and show at 8 p.m. • Pioneer Playhouse, 840 Stanford Road, Danville, Kentucky • pioneerplayhouse.com

This summer, Kentucky’s oldest outdoor theater celebrates its 77th anniversary with four different theatrical productions. On the schedule is “The Play that Goes Wrong,” a zany, award-winning comedy; “The Iron Baby Angel,” a heartwarming story adapted from the novel by Charles R. McDowell; and “Boeing Boeing,” a hilarious madcap comedy. The season will conclude with “Kings and Queens!,” a lively celebration of Elvis, Dolly Parton, and Loretta Lynn. 

2026 Summer Schedule:

• June 5-27 – “The Play that Goes Wrong”
• June 30-July 18 – “The Iron Baby Angel”
• July 21-Aug. 8 – “Boeing Boeing”
• Aug. 13-15 – “Kings and Queens!” 

Shaker Village Music on the Lawn

Fridays & Saturdays, May-Oct. (6:30-9:30 p.m.) • Shaker Village of Pleasant Hill, 3501 Lexington Rd.  • shakervillageky.org/events/music-on-the-lawn-2026/ 

Shaker Village’s Music on the Lawn offers live music, outdoor dining, and specialty cocktails around a fire pit in an idyllic historic farm setting. Outdoor dining is limited and weather-dependent. Attendees are encouraged to bring a chair.

The June and July schedule is below. Visit the event website for the full season schedule and additional details.

June and July Schedule:

• June 5 – Joanah Loomer
• June 6 – Shane White
• June 12 – J.J. Marrs
• June 13 – Andy Branton 
• June 19 – Randy Kaplan 
• June 20 – Dean Phelps (4-6 p.m.); Scott Collins (6:30-9:30 p.m.)
• June 26 – Andrea Gross
• June 27 – Cotter Hill
• July 3 – Ryan Branstetter
• July 4 – J.J. Marrs
• July 10 – Shane White
• July 11 – The Pastime Trio
• July 17 – Chris Weiss
• July 18 – Dean Phelps
• July 25 – Scott Collins
• July 31 – Buckwheat Husk 

Southland Jamboree

Thursdays at 7 p.m. (May-September) • Moondance Amphitheater, 1152 Monarch St. • southlandjamboree.org

This free, family-friendly bluegrass music concert series takes place at Moondance Amphitheater in Beaumont Center. Attendees are encouraged to bring lawn chairs or blankets as well as instruments for casual jam sessions. 

2026 Summer Schedule:

• June 4 – Rounder’s Station
• June 11 – Coaltown Dixie
• June 18 – Lonesome Express 
• June 25 – New Outlook
• July 2 – Six String Soldiers US Army Band 
• July 9 – Dale Ann Bradley 
• July 16 – Timberline Road
• July 23 – Mash Grass & Kids Camp kids 
• July 30 – West Liberty Mountain Boys
• Aug. 6 – Blue Debut
• Aug. 13 – Lincoln Mash & Heather Alley 
• Aug. 20 – Open Highway Band 
• Aug. 27 – CornMaiz String Band 

Summer Classics Film Series

Wednesdays through Sept. 9, 1:30 and 7:15 p.m.  • The Kentucky Theatre, 214 East Main St.  • kentuckytheatre.org 

For almost three decades, this popular series has brought classic films to the big screen with nostalgic lineups featuring something for every kind of film fan. In honor of the industry legends we said goodbye to in 2025, this year’s schedule includes films with Robert Redford, Diane Keaton, Gene Hackman, and Rob Reiner. Visit the website for tickets and additional details. 

2026 Film Series Schedule: 

• June 3 – “The Graduate”
• June 10 – “Spellbound”
• June 17 – “Lady and The Tramp”
• June 24 – “Annie Hall”
• July 1 – “Carmen Jones”
• July 8 – “This Is Spinal Tap”
• July 15 – “Bringing Up Baby”
• July 22 – “Indiana Jones and the Last Crusade”
• July 29 – “Cabaret”
• Aug. 5 – “All the Presidents’ Men”
• Aug. 12 – “The Philadelphia Story”
• Aug. 19 – “Touch of Evil”
• Aug. 26 – “Unforgiven”
• Sept. 2 – “Psycho”
• Sept. 9 – “The Big Lebowski”

Summer Nights in Suburbia

Every other Friday through Sept. 18, 7 p.m. • MoonDance Amphitheater, 1152 Monarch Dr. (Beaumont Circle) • lexingtonky.gov/playing/arts-events/summer-nights-suburbia 

Taking place every other Friday, this summer concert series features live music from a wide variety of genres. Attendees are encouraged to bring lawn chairs and blankets. Food vendors will be on-site. 

2026 Schedule: 

• June 12 – The Other Brothers
• June 26 – Eversett
• July 10 – 64 West
• July 24 – Boogie G and the Titanics
• Aug. 7 – NVRMND
• Aug. 21 – Magnolia Boulevard
• Sept. 4 – Honey Child
• Sept. 18 – TBA

Tahlsound Concert Series

Dates and venues vary • tahlsound.com

What started in 2017 as a full-day outdoor festival celebrating Lexington music has evolved into a series of smaller-scale concerts and pop-up events featuring local and regional acts, taking place throughout the warm-weather season.

Organized by a small collective of longtime friends and local musicians, the event has always focused heavily on the arts and business culture surrounding Southland Drive (the name Tahlsound is an anagram for “Southland”). Its home base is the Oleika Great Lawn, a grassy field behind Oleika Shriners’ Temple, which features a permanent stage and plenty of room for kids and dogs to roam in a contained, fenced-in space.

Times, tickets, and other details are available at the organization’s website. 

2026 Schedule: 

• June 28 – Back to Our Roots: A Celebration of Influential Lexington Musicians, featuring Maggie Lander, Idiot Glee and 10 Foot Pole (Olieka Temple)
• July 22-25 – Lexington Reggae Week, feat. Rik Jam & The Island Federation Band (West Sixth Brewery, Thursday Night Live, Gatton Park, and more)
• Aug. 23 – From the Bayou to the Bluegrass: A Celebration of Louisiana in Kentucky (Olieka Temple)

Tunes in the Vines

Sundays, 2-4:30 p.m. (through Nov. 1) • Equus Run Vineyards, 1280 Moores Mill Rd.  • equusrunvineyards.com/tunes-in-the-vines

Equus Run Vineyards’ “Tunes in the Vines” is a weekly concert series that features a variety of musicians. Wine and local beers are available for purchase and attendees are encouraged to bring lawn chairs and a picnic (no outside alcohol is permitted). 

The summer schedule is below. Visit the event website for the full season schedule and additional details.

Summer Schedule: 

• June 7 – The Strayz
• June 14 – Hole Shot Blues
• June 28 – VSP
• July 5 – Trippin’ Roots
• July 12 – Superfecta
• July 19 – Robert Eskridge and Southern Daze
• July 26 – Frequency 3
• Aug. 2 – Dane Sadler Band
• Aug. 9 – Branded Blue
• Aug. 16 – TBA
• Aug. 23 – Canvas
• Aug. 30 – 5 Below Band 

2026 Festivals & Events

Lexington Porch Fest

June 6-7, 12-6 p.m. • smileypete.com/lexingtonporchfest 

This free, city-wide community event features music performances on dozens of porches and lawns across the city. Attendees can either stay in their own neighborhoods or travel to other parts of town to enjoy live music and mingle with neighbors and community members. A full map and schedule are available on the website.

Lexington Lions Club Bluegrass Fair 

June 4-14 • Bluegrass Fairgrounds at Masterson Station Park • 3051 Leestown Road  • thebluegrassfair.com  

The Lexington Lions Club Bluegrass Fair has been a family tradition for more than 60 years. This annual event, which is a fundraiser for the club’s charitable work, features carnival-style rides, games, and attractions. Visit the event’s website as it nears for additional information and tickets. 

“It’s a Grand Night for Singing!”

June 12-14; 19-21 • Show start times vary • Singletary Center for the Arts, 405 Rose St. • finearts.uky.edu/music/events/its-grand-night-singing-2026 

For more than 30 years, this popular, Emmy-winning music revue has featured the best from Billboard to Broadway, starring UK Opera Theatre and community performers.

Spirit in the Bluegrass Festival

June 10-13 • Kentucky Horse Park, 4089 Iron Works Pkwy. • spiritinthebluegrass.com 

This three-day bluegrass music festival at the Kentucky Horse Park features some of the best pickers in the country. Created by the producers of the Ohio-based bluegrass festival SamJam, the family-friendly festival includes camping, food trucks, informal jam sessions, and performances from Union Town Bluegrass, Lonesome Express, Shadowgrass, The Steeldrivers, and more.

Beer Cheese Festival

June 13, 10 a.m.-5 p.m. • Downtown Winchester, Kentucky • beercheesefestival.com  

The Beer Cheese Festival will once again take over the streets of downtown Winchester with live music, retail vendors, Ale-8-One, and tons of beer cheese samples. Attendees are encouraged to cast their vote for their favorite beer cheese. 

PlayThink Festival

June 17-21 • Barren River Magic, 1696 Edwin Williams Road, Edmonton, Kentucky • playthinkfestival.com

PlayThink is a movement, music, and arts festival featuring “playshops” and entertainment options for a variety of ages, interests and physical ability levels. This unique, family-friendly camping event encourages creativity and playfulness with workshops on “flow” arts like hula hoop and yoga, kid’s arts and crafts, and performance art. Music acts including LIL FISH, Cornflower, Shylah Ray, and ANZA are slated to perform at this year’s event. 

SoulFeast 

June 18-28 • Various locations  • www.soulfeastweek.com

Now in its sixth year, SoulFeast is a joyful, week-long celebration of culture, cuisine, and community. Starting with a kickoff soirée at The Melroy (June 18), other highlights include Cocktails & Cigars, a high-energy block party taking over the new BC Garage on Third Street; SoulTeenth Festival at Gatton Park (June 20); and a Soulful Sunday Gospel Brunch at The V on The Vine, featuring food, fellowship and live music with two different seatings. Visit the event website for details and tickets.  

Great American Brass Band Festival

June 25-27 • Danville, Kentucky  • gabbf.org

Held annually on the campus of Centre College and in downtown Danville, this free, family-friendly event aims to preserve brass band music through a variety of programs, presentations, and performances. The event has moved to a later weekend this year to avoid overlaps with high school graduations, but the format remains the same as in years’ past. Visit the event website for the music line-up and additional details.

Fourth of July Celebration

July 1-5 • Various locations • lexingtonky.gov/playing/arts-events/fourth-july-celebration  

Lexington’s multi-day Fourth of July celebration typically includes an Ice Cream Social at Henry A. Tandy Centennial Park, a Patriotic Concert featuring The Lexington Philharmonic and a downtown parade and street festival that starts in the morning and culminates with a fireworks show at 10 p.m. Full details about this year’s festivities will be announced soon.

Lexington Burger Week

July 6-12 • Various locations • lexingtonburgerweek.com

One of the city’s most anticipated annual culinary events, Lexington Burger Week gives chefs from dozens of participating restaurants the chance to try creating the most unique burgers in town. Each restaurant features a one-of-a-kind burger not on its regular menu for $7-$8 throughout the week, making it easy for patrons to try out tons of new flavors and eateries. Fans can track their progress using the free Lexington Burger Week app. 

For a full list of participating restaurants, featured burgers and recommended pairings, visit the Lexington Burger Week website as the event nears.

Shakespeare in the Park: “Much Ado About Nothing”

July 10-12; 16-19 (Gates at 6:30 p.m.; show at 8 p.m.) • Woodland Park,601 E. High St. • antagonist.productions 

Antagonist Productions presents one of Shakespeare’s most popular comedies. Directed by Drew Davidson, with live music and local vendors enhancing the experience, audiences can expect an unforgettable evening celebrating creativity, connection and community, in an outdoor park setting. Both weekends will feature live music before the play begins.  

Harry Dean Stanton Fest 

July 10-12 • Various venues • harrydeanstantonfest.org

Since 2011, Lexington’s Harry Dean Stanton Festival has paid tribute to the late iconic character actor and Kentucky native who appeared in over 200 films over the course of his prolific career. Spread out over multiple days and venues, the event typically includes film screenings, music performances, and special guest appearances; this year’s event will mark what would have been Stanton’s 100th birthday, and will kick off with a cemetery screening of “Cool Hand Luke” at Blue Grass Memorial Gardens (July 10) and conclude with a 4k restoration screening of “Paris, Texas” at the Kentucky Theatre (July 12). 

The event will also feature film screenings at the Farish Theater (including three festival debuts: “Raffery and the Gold Dust Twins,” “Uforia” and “The Black Marble”); an all-star table read of an un-produced screenplay that Allison Anders wrote for Harry in the 1980s entitled “Lost Highway;” and a show at the Green Lantern featuring former Harry Dean Stanton and the Repo Men bandmates James Intveld and Billy Swan. Full schedule and more details will be posted soon at the event website.

Ballet Under the Stars

July 29-Aug. 2 (8 p.m. pre-show, with main curtain at 9 p.m.) • Woodland Park, 601 East High St. • lexingtonky.gov/playing/arts-events/ballet-under-stars 

Ballet Under the Stars is an outdoor dance celebration featuring a youth production followed by a main show starring professional dancers from Kentucky Ballet Theatre. This year’s pre-show will be “Princess Vignettes,” featuring stories from Rapunzel, Cinderella, Belle, Moana, and Snow White. The main show will follow. Attendees are encouraged to bring lawn chairs or blankets for seating. 

CRAVE food + music festival 

July 31-Aug. 1  • Gatton Park on Town Branch, 3051 Leestown Road  • www.cravelexington.com

This annual, family-friendly food and music festival is produced by Smiley Pete Publishing featuring a curated selection of local and regional food vendors, live music, chefs, special food performances, craft beer and cocktails. This year’s lineup includes Honeychild, Velvet Elvis, Club Dub and more – visit website for more details as the event nears!

Shaker Village Craft Fair

Aug. 1-2, 10 a.m.-5 p.m. • Shaker Village of Pleasant Hill, 3501 Lexington Rd.  • shakervillageky.org/events/craft-fair-2026 

One of Kentucky’s top craft-centric happenings, the Shaker Village Craft Fair attracts elite regional artisans as well as up-and-coming artists. The annual event offers a wide assortment of crafts, from pottery, jewelry, and glassware to woven rugs, needlecraft, basketry, leather goods, floral design, and Shaker reproductions. General admission to Shaker Village — which includes access to historic tours, exhibits, and other Shaker Village experiences — is discounted during this weekend. Attendees can also enjoy the Shaker Village bar, live music, and food trucks.

Picnic with the Pops: “Pops Goes Country! Country Hits – Songs from Nashville”

Aug. 8 • Gates at 4 p.m.; show at dusk • The Meadow at Keeneland, • 4201 Versailles Rd.  • www.lexpops.com 

Picnic with the Pops has long been a favorite summer event in Lexington for over four decades. Each year, The Lexington Philharmonic teams up with a special guest performer to present an evening of popular music with symphonic accompaniment in the idyllic Keene meadow at Keeneland. Attendees can purchase tables of eight (tables and chairs provided) or general admission seating (bring your own chairs/blankets) and bring a picnic dinner to enjoy. Cocktail, costume and table decorating contests add to the festivities.

For this year’s show, a cast of Nashville-based guest artists will join the Lexington Philharmonic for an evening of symphonic renditions of beloved classic country songs like “Folsom Prison Blues,” “Devil Went Down to Georgia,” “Always On My Mind,” “Jolene,” and “Wichita Lineman,” with a few modern country songs mixed in. Expect to hear solid gold hits we know and love, made famous by artists like Johnny Cash, Dolly Parton, Willie Nelson, Alison Krauss and more.

Woodland Art Fair

Aug. 15-16 (10 a.m.-6 p.m. Saturday; 10 a.m.-5 p.m. Sunday) • Woodland Park, 601 E. High St. • woodlandartfair.org

Now in its 50th year, the Woodland Art Fair, produced by the Lexington Art League and Lexington Parks & Recreation, is one of Lexington’s most celebrated cultural events. It features artists and makers selling unique, handcrafted items ranging from ceramics and wood art to jewelry and photographs, along with food and beverage vendors, live music, and more in a relaxed and shaded park setting.

Chevy Chase Street Fair

Aug. 22, 4-10 p.m. • Euclid Avenue, between Ashland Ave. and High St.

The ever-popular block party Chevy Chase Street Fair returns with dozens of local vendors, live music, kids’ activities, street food, craft beer and cocktails and neighborhood camaraderie. Keep an eye on social media for the full list of vendors, bands and other details, as the event nears. Chevy Chase Street Fair is produced by Smiley Pete Publishing in partnership with Chevy Chase Merchants Association.