2023 Summer Fun Guide

We’ve rounded up dozens of live music shows, film screenings, food festivals, dance performances and other fun stuff that only happens as the days get longer and the weather gets warmer. Get out your calendars and plan your summer with our annual summer fun guide!

Recurring Series

A look at various live music, film, theater and other recurring series taking place regularly throughout the warm weather months. Click each event title for a link to more info.

Big Band & Jazz Series

Tuesdays through Aug. 15 (7-8:30 p.m.) • Moondance Amphitheater, 1152 Monarch St. (May-June) and Ecton Park, 956 Turkey Foot Road (July-August)

One of Lexington’s longest running and most beloved concert series returns with a full schedule of free weekly big band and jazz music, with the season split between two popular local parks: Moondance Amphitheater (May-June) and Ecton Park (July-August). Patrons are encouraged to bring a lawn chair or blanket for seating.

Moondance Amphitheater Big Band & Jazz Schedule:

• June 6 – Kentucky Jazz Repertory Orchestra
• June 13 – Tim Lake and the Blue Jazz Persuaders
• June 20 – Brett Evans Trombone Jazz Ensemble
• June 27 – Lexington Summer Concert Band

Ecton Park Big Band & Jazz schedule: 

• July 11 – DiMartino/Osland Jazz Orchestra
• July 18 – Walnut Street Ramblers
• July 25 – Miles Osland Little Big Band with Vince DiMartino
• Aug. 1 – Ross Whitaker Quintet
• Aug. 8 – Marlin McKay Quartet
• Aug. 15 – Osland/Dailey Jazztet

Free Friday Flicks

Fridays in June (Pre-show activities start at 7 p.m.; movies start at dark) • Jacobson Park, 4001 Athens-Boonesboro Road

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

2023 Free Friday Flicks Schedule:

• June 2 – “Turning Red” (pre-show yoga session)
• June 9 – “Lightyear” (pre-show performance from Sora Aerial Arts)
• June 16 – “The Bad Guys” (pre-show karate demonstration)
• June 23 – “Puss In Boots” (pre-show fencing demonstration)
• June 30 – “Minions: The Rise of Gru” (pre-show dance party)

Music on the Lawn at Shaker Village

Fridays and Saturdays through October (6:30 p.m.) • Shaker Village of Pleasant Hill, 3501 Lexington Road

Shaker Village’s Music on the Lawn offers an opportunity to enjoy 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 pack a chair.

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

June and July Shaker Village Music on the Lawn Schedule:

• June 2 – Warren Byrom
• June 3 – Buck the Taxidermist
• June 9 – Venus Lori
• June 10 – Chris Weiss
• June 16 – Carrie Johnson
• June 17 – Greg Schaber
• June 23 – Shane White
• June 24 – Lylak
• June 30 – Buck the Taxidermist
• July 1 – Warren Byrom
• July 7 – Spooky Fox
• July 8 – Scott  Collins
• July 14 – Shane White
• July 15 – Randy Kaplan
• July 21 – Carrie Johnson
• July 22 – Joanah Loomer
• July 28 – Matt Green
• July 29 – Chris Weiss

Northside Nights

July 14, 28; Aug. 11, 25 (6-9 p.m.) • Castlewood Park, 201 Castlewood Drive

Northside Nights is an outdoor concert series that takes place every other Friday. Attendees are encouraged to bring lawn chairs and blankets for seating while enjoying R&B, soul, funk and dance music. Check the website for the schedule.

Pioneer Playhouse

Tues.-Sat., June 9-Aug. 12 (dinner at 7 p.m.; show at 8:30 p.m.) • Pioneer Playhouse, 840 Stanford Road, Danville

In celebration of its 74th season, Kentucky’s oldest outdoor theater will feature three different theater performances as well as a stand-up comedy weekend. All performances are held outside, and attendees are encouraged to make advance dinner reservations for a farm-fresh meal at the theater as well.

2023 Pioneer Playhouse Schedule:

• June 9-July 1 – “Blue Suede Shoes: A Sergeant Elvis Presley Murder Mystery”
• July 4-22 – “Farce of Nature”
• July 25-Aug. 12 – “Kosher Lutherans”
• Aug. 18-19 – Stand-Up Comedy Weekend with Lee Cruse

Southland Jamboree

Thursdays through Sept. (7 p.m.)  • Moondance Amphitheater, 1152 Monarch St.

This long-running series, which originally took place on Southland Drive in its early years, presents free, outdoor bluegrass music concerts in a family-friendly setting. Attendees are encouraged to bring lawn chairs or blankets to the concerts – and instruments for the casual jam sessions that often take place following the show. Check the website for the listing of food trucks that will be present for each week’s event.

2023 Southland Jamboree Schedule

• June 1 – Fast Track
• June 8 – Ida Clare
• June 15 – Wildfire
• June 22 – The Daltons
• June 29 – Branchwater Kin
• July 6 – Gibson Davis & Copper Valley
• July 13 – Hancock & Shouse
• July 20 – Dove Creek
• July 27 – Kentucky Just Us
• Aug. 3 – Rickey Wasson Band
• Aug. 10 – Old Towne Project
• Aug. 17 – Hammertowne
• Aug. 24 – Fenced In
• Aug. 31 – EKU Bluegrass Band

Summer Classic Film Series

Wednesdays through Aug. 30 (1:30 and 7:15 p.m.)  • The Kentucky Theatre, 214 East Main St.

For nearly two decades, The Kentucky Theatre has been screening classic films on Wednesdays from late May until early September. As usual, this year’s robust lineup features something for every film fan. Visit the series’ website for tickets and additional details.

2023 Summer Classic Film Series Schedule: 

• June 7 – “Raging Bull”
• June 14 – “Fiddler on the Roof”
• June 21 – “The Empire Strikes Back”
• June 28 – “His Girl Friday”
• July 5 – “Rebel Without a Cause”
• July 12 – “Jaws”
• July 19 – “The Maltese Falcon”
• July 26 – “Pinocchio”
• Aug. 2 – “The Princess Bride”
• Aug. 9 – “Adam’s Rib”
• Aug. 16 – “Goodfellas”
• Aug. 23 – “The Last Picture Show”
• Aug. 30 – “Monty Python and the Holy Grail”

Summer Nights in Suburbia

Every other Friday through Sept. (7-9 p.m.) • Moondance Amphitheater, 1152 Monarch Drive (Beaumont Circle)

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 and beer vendors will be on-site.

2023 Summer Nights in Suburbia Schedule:

• June 9 – Bedford
• June 23 – Run Katie Run
• July 7 – The Minks
• July 21 – Born Cross Eyed
• Aug. 2 – Milenio Salsa Band & The Salsa Center
• Aug. 18 – Honeychild
• Sept. 1 – Baja Yetis

Tahlsound Concert Series

Fourth Sunday of the month, 5 p.m. • 302 Southland Drive

Formerly a single day festival, Tahlsound reorganized as a regular concert series that takes place monthly (April-September), featuring food, beer and retail vendors, live music and a family-friendly atmosphere. Gates open at 5 p.m. with music starting at 6 p.m.

This year’s summer dates are June 10, July 23, Aug. 27 and Sept. 24. Visit the website for info about the monthly lineups and additional details.

Thursday Night Live 

Thursdays through Oct. (5-8 p.m.) • Fifth Third Bank Pavilion at Tandy Park, 251 W. Main St.

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 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.   

2023 Thursday Night Live Summer Schedule:

• June 1 – Five Below Band
• June 8 – Positive Movement Band
• June 15 – Paul Childers
• June 22 – The Johnson Brothers
• June 29 – Vanguard
• July 6 – Lauren Mink Band
• July 13 – The BANdj Experience
• July 20 – Kimberly Carter & Carryin’ On
• July 27 – Nightflyer: the Ultimate Eagles Tribute Band
• Aug. 3 – 64west
• Aug. 10 – Tim Talbert Project
• Aug. 17 – The Twiggenburys
• Aug. 24 – Kenny Owens & Group Therapy
• Aug. 31 – Mercy Men

Tunes in the Vines

Sundays through Nov. (2-4:30 p.m.) • Equus Run Vineyards, 1280 Moores Mill Road

Now in its 25th year, 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.

Visit the event website for the full season lineup.

2023 Tunes in the Vine Summer Schedule:

• June 4 – Station 22 ½
• June  11 – Rock Steady
• June  18 – Steve Dooley
• June 25 – Bigg Sugg & the Jazz Funkers
• July 2 – Bootsie Heart and Soul
• July 9 – Matthew Castle
• July 16 –  Chris Carpenter
• July 23 – Logan Leet
• July 30 – Mid Life Harmony
• Aug. 6 – The Hazlett Brothers Band
• Aug. 13 – Whiskey River
• Aug. 20 – Superfecta Band
• Aug. 27 – Lee Carroll Trio

Festivals & Events

Great American Brass Band Festival

June 1-4 • Danville

The Great American Brass Band Festival is a free, family-friendly event held annually on the campus of Centre College and in downtown Danville. Now in its 33rd year, the festival aims to preserve brass band music through a variety of programs, presentations and performances. Visit the event website for the music line-up and additional details.  

Railbird

June 3-4 • The Infield at Red Mile,1200 Red Mile Road

After taking place at Keeneland for its first two years – and taking a hiatus in 2022 – Lexington’s largest music festival returns in 2023 albeit at a new venue. Performers at the festival are primarily of the country/Americana variety, including Tyler Childers, Zach Bryan, Jenny Lewis, Weezer, Marcus Mumford, Nathaniel Rateliff and more. Tickets sold out the first day they were available; while resale tickets may be available as the event nears, patrons are urged to use caution and only purchase from reputable resale sites.

Lexington Lions Club Bluegrass Fair

June 8-18 • Bluegrass Fairgrounds at Masterson Station Park, 3051 Leestown Road 

Presented by the Lexington Lions Club, the Bluegrass Fair has been an annual family tradition for more than 60 years, with carnival-style rides and attractions provided by Kissell Entertainment, and a variety of agricultural events as well. For additional information and tickets, visit the event’s website as it nears.

‘It’s a Grand Night for Singing!’

June 9-18 • Singletary Center for the Arts, 405 Rose St.

This year marks the 31st anniversary for University of Kentucky Opera Theatre’s “It’s a Grand Night for Singing!” Starring more than 100 UK Opera Theatre and community performers, this popular music revue features the best from Billboard to Broadway.

Southland Street Fair

June 10 (3-8 p.m.) • Southland Drive (near the corner of Rosemont Garden)

With food, vendors and music entertainment (curated by the organizers of Tahlsound Concert Series), this annual outdoor festival-style event offers fun for the whole family.

PlayThink Festival

June 14-18 • Terrapin Hill Farm, 3696 Mackville Road, Harrodsburg

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 focusing on “flow arts” and other mind- and heart-opening exercises, from hula hoop and yoga to ecstatic dance and aerial arts. The festival also features kids’ arts and crafts, and live music from Equanimous, Toni Jones and Ruby Chase and many more.

SoulFeast

June 17-25 • Various venues

SoulFeast is a festival featuring many events celebrating local Black culture, with a special focus on the food and beverage industry. On June 17, SoulFeast will present SoulTeenth Fest, a Juneteenth Festival celebrating Black liberation and culture through live music, art, agriculture and food, at Moondance Amphitheater. During Black Restaurant Week (June 19-25), presented in partnership with Black Soil KY, participating restaurants will create a unique, off-menu food entrée for $10, with each entree featuring at least one ingredient sourced from a Black farmer or producer in Kentucky. Additional events include a Diaspora Dinner highlighting dishes from Western Africa, the Caribbean and America (June 16 at Harper Hill), a Cocktails & Cigars event at Jack’s Sandbar (June 17), a Hip Hop Brunch at The Grove (June 18), a Black History Walking Tour presented in conjunction with Bites of the Bluegrass (June 19) and a Soulful Sunday Gospel Brunch (June 25).

Lexington PRIDE Festival

June 24, 11 a.m.-10 p.m. • Central Bank Center, 430 W. Vine St.

Formerly taking place on the courthouse plaza, PRIDE now takes place indoors but still focuses on empowering and bringing awareness to the LGBTQIA+ community. Attracting thousands of attendees from central Kentucky and the surrounding regions, the family-friendly event features live entertainment, speakers, a diverse array of vendors, food trucks, community booths and activities.

Lexington Fourth of July Celebration

July 1-4

The city of Lexington will celebrate July 4, starting with a Red, White & Blues concert at 5:30 p.m. on Sat., July 1 at Moondance Amphitheater, featuring local musicians Tee Dee Young and Willie Eames. The city will host an Ice Cream Social on July 2 at Henry A. Tandy Centennial Park (2-4 p.m.) and a Patriotic Concert with the Lexington Philharmonic on the steps of Transylvania University’s Old Morrison building on July 3 (pre-show starts at 5:30 p.m.; main show at 8 p.m.). On Tues., July 4, the city will host the Fourth of July Festival and Market, taking place at the Courthouse Plaza and Henry A. Tandy Centennial Park from 10 a.m.-3 p.m., with the Fourth of July Parade taking place downtown at noon and a Fireworks Spectacular starting at 10 p.m. that evening.

Lexington Burger Week

July 10-16 • Various locations

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

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

Lexington Burger Week is produced by Smiley Pete Publishing, this magazine’s parent company.

Harry Dean Stanton Fest

July 14-16 • Various venues

This annual film festival pays tribute to the prolific late character actor Harry Dean Stanton, a Kentucky native who appeared in nearly 200 films and television episodes over his illustrious six-decade career. Specifics will be announced as the event nears, but the festival typically features a handful of special film screenings, guest appearances, Q&As and other special events. 

Chevy Chase Street Fair

July 22 (4-10 p.m.) • Euclid Avenue

The ever-popular block party Chevy Chase Street Fair returns with more than 30 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, this magazine’s parent company, in partnership with Chevy Chase Merchants Association.

Ballet Under the Stars 

Aug. 2-6 (8 p.m. pre-show with main curtain at 9 p.m.) • Woodland Park, 601 East High St.

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. Attendees are encouraged to bring lawn chairs or blankets for seating.

Picnic with the Pops: An Evening of  Symphonic Disco with Boogie Wonder Band 

Aug. 12 • The Meadow at Keeneland, 4201 Versailles Road

Picnic with the Pops has been a favorite summer event in Lexington for more than three decades. Each year, The Lexington Philharmonic teams up with a special guest to perform an evening on popular music in the idyllic meadow at Keeneland near Keene Barn. 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. (Table holders from previous years are allowed the first opportunity to renew their tables.)

This year’s show will be An Evening of Symphonic Disco with Boogie Wonder Band. Dressed in eye-popping Las Vegas-inspired costumes, the 10-piece band will play a set of funk-a-liscious, disco-strutting jams from the ’70s. Patrons are encouraged to dress their tables – and themselves! – in theme.

Woodland Art Fair 

Aug. 19-20  (10 a.m.-6 p.m. Saturday; 10 a.m.-5 p.m. Sunday) • Woodland Park, 601 E. High St.

The Woodland Art Fair, produced by the Lexington Art League and Lexington Parks and Recreation, is a highly anticipated, family-friendly event designed to celebrate art in a leisurely setting while enjoying the great outdoors. Featuring artists and makers selling unique, handcrafted items, ranging from ceramics and wood art to jewelry and photographs, the event has been one of Lexington’s most celebrated cultural events for more than 40 years.

Crave Food & Music Festival 

Aug. 26-27 (11 a.m.-10 p.m. Saturday; 11 a.m.-7 p.m. Sunday)

Bluegrass Fairgrounds at Masterson Station Park, 3051 Leestown Road

This annual, family-friendly festival celebrating Lexington-area food and music celebrates its 10th installment this year. Designed to encourage culinary exploration, the event features dozens of food vendors offering a variety of different-sized portions, as well as demos from food and beverage experts throughout the weekend. With live music from local and regional bands, as well as craft beer and cocktails, kid-friendly activities, retail vendors and a classic car show, the event features something for everyone.

This year’s music lineup includes performances from 10 Foot Pole, Ernie Johnson From Detroit, Bee Taylor, Big Maracas, The Jesse Lees, Club Dub, Devine Carama, FrigidKitty, New Beckham County Ramblers and more – visit the website as the event nears for more info.

Crave Food & Music Festival is produced by Smiley Pete Publishing, this magazine’s parent company.

Expansion: Lexington’s Psychedelic Experience & Music Festival 

Aug. 24-26 • The Burl (475 Thompson Road), Kentucky Theatre, 21c Museum Hotel

Now in its fifth year, this local celebration of psychedelic and experimental music and art has moved to a new date and expanded its format to include a Thursday night film screening at the Kentucky Theatre (a retrospective of local artist Robert Beatty, followed by a screening of “Chunky Shrapnel,” a documentary about the Australian psych band King Gizzard and the Lizard Wizard), as well as a pre-party at 21c Museum Hotel on Friday.

For the main event, a full-day of mind-bending music and art will take place at The Burl on Saturday, Aug. 26, utilizing that venue’s outdoor stage. This year’s music lineup will be headlined by experimental, beat-centric artist TOBACCO, with support from King Buffalo, Hooveriii, Liz Cooper, Sweet Country Meat Boys and more, with visual artists who specialize in analog liquid light, video synthesis and projection-mapping providing visuals via LED screens. More details and a schedule of events will be unveiled in the coming weeks.