Summer Entertainment Guide 2022 – Smiley Pete Publishing

Following a shaky couple of years for events, this year’s schedule of summer fun-time activities is brimming once again. We’ve highlighted some favorite local warm-weather concert series, festivals and other events.

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. 9, 7-8:30 p.m. May and June concerts take place at MoonDance Amphitheater, 1152 Monarch Street. July and August concerts take place at Ecton Park, 956 Turkey Foot Road.

One of Lexington’s longest running and most beloved concert series returns with a full schedule of weekly big band and jazz music planned at Moondance Amphitheater (May and June concerts) or Ecton Park (July and August concerts). Picnics are encouraged and patrons should bring a lawn chair or blanket for seating. 

Moondance Amphitheater schedule:

June 7 – DiMartino/Osland Jazz Orchestra 

June 14 – Walnut Street Ramblers 

June 21 – Brass Impact 

June 28 – Lexington Summer Concert Band

Ecton Park schedule: 

July 5 – Miles Osland Little Big Band w/Vince DiMartino

July 12 – Brett Evans Trombone Jazz Ensemble 

July 19 – Ozmosis 

July 26 – Tim Lake and the Blue Jazz Persuaders 

Aug. 2 – Uncle Sam’s Bait Shop 

Aug. 9 – Osland/Dailey Jazztet 

Friday Flicks

Fridays, June 3-24. Activities start at 7 p.m. and movie starts 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. 

2022 Film Schedule:

June 3 – “Raya and the Last Dragon”

June 10 – “Willy Wonka & the Chocolate Factory”

June 17 – “Sing 2”

June 24 – “Encanto”

Music on the Lawn

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

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 pack a chair.

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

June and July Schedule:

June 3 – Spooky Fox 

June 4 – Randy Kaplan 

June 10 – Josh Mitcham 

June 11 – Chris Weiss 

June 17 – Kylie Miller 

June 18 – New Beckham County Ramblers 

June 24 – Warren Byrom 

June 25 – Carrie Johnson 

July 1 – Be Square 

July 2 – Dean Phelps

July 3 – New Beckham County Ramblers 

July 8 – Alicia Hollingshead 

July 9 – Derek Spencer 

July 15 – Jarrod Stratton 

July 16 – Liz Bowman 

July 22 – Carrie Johnson 

July 23 – Scott Miller

July 29 – Lylak 

July 30 – Chris Weiss

Northside Nights

Every other Friday through September 2, 6:30 p.m. Castlewood Park, 201 Castlewood Drive. 

Northside Nights, which debuted last year, 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. 

2022 Schedule:

June 10 – Positive Movement 

June 24 – Special Sessions 

July 8 – Benny J & Friends 

July 22 – Elite 7 

Aug. 5 – One Sound 

Aug. 19 – The Tim Talbert Project

Sept. 2 –  Rhythm & Soul

Pioneer Playhouse

Tues.-Sat., June 10-Aug. 6. Dinner at 7 p.m.; show at 8:30 p.m. Pioneer Playhouse, 840 Stanford Road, Danville.

For its 73rd season, Kentucky’s oldest outdoor theater features a lineup that includes three hilarious and heartwarming comedies and two special music weekends.

Before the plays, a home-cooked BBQ dinner is available for purchase (reservations required), accompanied by guitar playing by Ms. Charlotte, who has performed at the theater for more than 50 years.

Theatre Schedule:

June 10-July 2 – “Dracula Bites”

July 5-July 23 – “Southern Fried Nuptials”

July 26-Aug. 6 – “Cockeyed”

Music Schedule:

Aug. 12-13 – “Elvis and Patsy Cline Together Under the Stars,” featuring tribute artists Barry Lockard and Nathalie Berry 

Aug. 20 – Latin Night with No Rules Banda (doors at 7 p.m., music at 8 p.m.)

Southland Jamboree

Select Thursdays at 7 p.m. (June-September). MoonDance Amphitheater, 1152 Monarch Street.

While the day and location of the Southland Jamboree (originally taking place Monday nights on Southland Drive) have shifted in recent years, the series’ focus on providing free, outdoor bluegrass music concerts in a family-friendly setting remains. Attendees are encouraged to bring lawn chairs or blankets to the concerts – and instruments, for the jam sessions that often take place afterward.

2022 Summer Schedule

June 2 – Jim Hurst Bluegrass Band

June 9 – Fast Track

June 16 – Blue Eagle Band

June 23 – Custom Made Bluegrass

June 30 – Wolfpen Branch

July 7 – Maddie Murray and Darren Wasson Band

July 14 – Hammertowne

July 21 – Cane Run Bluegrass

July 28 – Alan Bibey & Grasstowne

Aug. 4 – Olde Towne Project 

Aug. 11 – Don Rigsby 

Aug. 18 – Ida Clare

Aug. 25 – New Coon Creek Girls Reunion

Summer Classic Film Series

Wednesdays through September, 1:30 and 7:15 p.m.The Kentucky Theatre, 214 East Main Street. 

For nearly two decades, The Kentucky Theatre has been screening classic films on Wednesdays from late May until early September. While the theater is now under new ownership, the tradition continues this year, with a robust lineup that has something for every film fan. Visit the series website for tickets and details. 

2022 Classic Film Series Schedule: 

June 1 – “Roman Holiday”

June 8 – “Star Wars”

June 15 – “A Patch of Blue”

June 22 – “Goldfinger”

June 29 – “2001: A Space Odyssey”

July 6 – “The Big Sleep”

July 13 – “An American Werewolf in London”

July 20 – “Sleeping Beauty” 

July 27 – “Bonnie and Clyde”

Aug. 3 – “Stand By Me”

Aug. 10 – “The Man Who Knew Too Much”

Aug. 17 – “West Side Story”

Aug. 24 – “Shakespeare in Love”

Aug. 31 – “The Godfather”

Summer Nights in Suburbia

Every other Friday, 7 p.m. (June 3-Aug. 26). 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. 

2022 Schedule:

June 3 – DJ Rice

June 17 – Lauren Mink Band

July 1 – The Bedford Band

July 15 – Brother Smith

July 29 – Honeychild

Aug. 12 – DeeOhGee

Aug. 26 – NVRMND

Tahlsound Concert Series

Fourth Sunday of the Month, 5 p.m. Oleika Temple Lawn, 326 Southland Drive.

Formerly a daylong festival, Tahlsound has reorganized as a regular concert series taking place the fourth Sunday of the month (April-September) on the lawn behind Oleika Temple, featuring food, beer and retail vendors, live music and a family-friendly atmosphere. Gates open at 5 p.m. with music starting at 6.

This year’s summer dates are June 27, July 25, Aug. 22 and Sept. 26. Visit the website for lineups and other details.

Thursday Night Live 

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

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.

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

2022 Summer Schedule:

June 2 – Five Below Band

June 9 – Paul Childers

June 16 – The Johnson Brothers

June 23 – 64West

June 30 – Nightflyer: The Ultimate Eagles Tribute Band

July 7 – Honeychild

July 14 – The Ranahans

July 21 – Boogie G & The Titanics

July 28 – Encore of Lexington

Aug. 4 – The Big Maracas

Aug. 11 – Tim Talbert Project

Aug. 18 – The Twiggenburys

Aug. 25 – Kenny Owens & Group Therapy

Tunes in the Vines

Sundays, 2-4:30 p.m. (through July 10). Equus Run Vineyards, 1280 Moores Mill Road. 

Now in its 24th 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 and attendees are encouraged to bring lawn chairs and a picnic (no outside alcohol is permitted). 

2022 Schedule:

May 22 – The Twiggenburys

May 29 – Bigg Sugg & the Jazz Funkers 

June 5 – Hi-5

June 12 – Rocksteady

June 19 – BeSquare

June 26 – Robert Eskridge

July 3 – Station 22½

July 10 – Ebony and Ivory

2022 Festivals and Events

Great American Brass Band Festival

June 2-5, Danville.

The Great American Brass Band Festival is a free, family-friendly event held annually on and around the campus of Centre College and in downtown Danville. Now in its 32nd year, the festival aims to preserve brass band music through a variety of programs, presentations and performances. This year’s performers include the Walnut Street Ramblers, Mike Wade & the Nasty Nati Brass Band, Southern Stars Symphonic Brass, Boston Brass and more. Visit the event website for the music line-up and additional details.  

Lexington Lions Club Bluegrass Fair

June 9-19. Bluegrass Fairgrounds at Masterson Station Park, 3051 Leestown Road.

The Lexington Lions Club Bluegrass Fair has been a family tradition for 60 years. This annual event features carnival rides, games and enjoyable attractions provided by Kissell Entertainment. All-new entertainment lineup for 2022 features The Rocketman Valencia, a human cannonball who has appeared in some of the world’s biggest events, as well as Live Shark Encounter, pig racing, nightly live music, exhibits and fair food favorites, including funnel cakes, cotton candy, gourmet corndogs, turkey legs, pizza, deep-fried delights and the best Mexican food in central Kentucky. Gates open at 5 p.m. during the week and 3 p.m. on weeknights.

“It’s a Grand Night for Singing!”

10-12; June 17-19. Singletary Center for the Arts, 405 Rose Street. 

This year marks the 30th anniversary for University of Kentucky Opera Theatre’s “It’s a Grand Night for Singing!” The Emmy Award-winning singalong spectacular and music revue features the best from Billboard to Broadway, starring more than 100 UK Opera Theatre and community performers. 

Friday and Saturday performances take place at 8 p.m., Saturday matinees at 2 p.m. and Sunday performances at 6 p.m. Doors open 30 minutes before showtime.

PlayThink Festival

June 15-19. Terrapin Hill Farm, 3696 Mackville Road, Harrodsburg.

PlayThink is an annual grassroots festival focusing on movement, music and arts. Featuring “playshops” and entertainment options for a variety of ages, interests and physical ability levels, this unique, family-friendly camping event encourages creativity, mindfulness and playfulness, with workshops on “flow arts,” such as hula hoop, aerial silks and acro-yoga, as well as kid’s arts and crafts, performance art and more.

Music acts including Desert Dwellers, Autograf and Equanimous are slated to perform at this year’s event. A full schedule of performances and playshops is available at the event website.


June 17-26.

SoulFeast Week is a 10-day celebration of Black culinary culture, highlighting Black restaurateurs, farmers and chefs in central Kentucky. Through educational events, curated experiences and enjoying great food, SoulFeast Week is an opportunity for Kentuckians of all races and backgrounds to support Black businesses by putting their money where their mouths are – literally.

Events include a Kickoff Soiree at the Marriott CityCenter (June 17); SoulTeenth Fest, an outdoor festival featuring live music and food trucks at MoonDance Amphitheater (June 18); a Korbel Hip Hop Brunch with bottomless mimosas (June 19); SoulFeastWeek, a traditional food week where participating Black-owned restaurants will each offer a unique off-menu item for $10 (June 20-26); and lots more.

Lexington Boutique Week

June 20-25. Various locations.

Lexington Boutique Week is designed to provide shoppers a chance to upgrade their wardrobes while supporting the best of the city’s local retail businesses. During the six-day event, more than 20 participating boutiques will offer exclusive “deals and steals” to entice shoppers. Visit the event’s website for a full list of participating stores and promotions. 

Lexington Boutique Week is produced by Smiley Pete Publishing (this magazine’s parent company).

Lexington Pride Festival

June 25, 11 a.m.-10 p.m. Robert F. Stephens Courthouse Plaza, 120 N. Limestone Street.

For more than a decade, this annual celebration has been empowering and bringing awareness to the LGBTQIA+ community. Taking place in a family-friendly environment and attracting thousands of attendees from central Kentucky and the surrounding regions, the festival-style event features live entertainment, speakers, a diverse array of vendors, food trucks, community booths, activities and more.

Lexington Burger Week

July 11-17. Various locations. 

One of the city’s most anticipated annual culinary events, Lexington Burger Week returns in 2022, giving chefs from

dozens of participating restaurants the chance to try once again to create the most unique burgers in town. Each restaurant will feature a one-of-a-kind burger throughout the week that’s not on their regular menu for $7, 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 15-17. Various locations.

Now in its 10th year (not counting a small virtual event that took place early in the pandemic), this annual festival pays tribute to the prolific character actor, singer and songwriter Harry Dean Stanton, a native of Kentucky 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. 

This year’s festival is slated to include appearances from Kentucky-born screenwriter and director Allison Anders, who was a production assistant in the film “Paris, Texas” (a film in which Stanton had a rare lead role); country-rock performer Billy Swan, who will present an evening of music and storytelling where he will recount memories of his decades of friendship with Harry Dean; Kentucky author Silas House, who will present a special screening of “Where the Lilies Bloom”; and biographer Joe Atkins, author of “Harry Dean Stanton, Hollywood’s Zen Rebel.” The festival events will take place at Kentucky Theatre, Base 249, the Farish Theatre and the Green Lantern.

Character Fest

July 22-25. The Kentucky Theatre

A new spin-off of Harry Dean Stanton Fest will continue the spirit of that event by honoring a different character actor or actress every year. The first honoree is writer/director/singer/actor Sy Richardson, who co-starred in “Repo Man” alongside Harry Dean Stanton. The weekend will include a retrospective of some of Richardson’s most notable films, many of which are classics of American independent film. Richardson will participate in Q&A’s following select screenings.

More info and the schedule will soon be available at

Crave Food & Music Festival 

July 30-31 (12-11 p.m. Saturday; 12-7 p.m. Sunday). Bluegrass Fairgrounds at Masterson Station Park, 3051 Leestown Road. 

Featuring 40 local food vendors, live music, special food performances, craft beer and cocktails, kid-friendly activities, a classic car show, corn hole tournament and more, this annual, family-friendly food and music festival is the biggest celebration of Lexington’s culinary culture. Designed for exploration, the festival provides an opportunity for patrons to sample from dozens of food vendors, including local restaurants, food trucks and more. The Crave Kitchen Stage, emceed by celebrity chef “Lord Honey” Jason Smith, will feature a full weekend of culinary programming curated in partnership with Black Soil, including demos, competitions and more. Two full bars will offer special craft cocktails, beer and wine, and can stations throughout the festival will offer quick places to grab a cold beverage of choice. Stay tuned for special culinary pop-up events taking place throughout the weekend.

Another highlight of the festival is a live music lineup ranging from garage rock to Americana, bluegrass, blues and soul. This year’s stage will feature DeeOhGee, Restless Leg String Band, Bee Taylor, Scott T. Smith, The Minks, Hot Brown Smackdown, Champs of the Sun, Girl Tones, DeBraun Thomas and Maggie Lander

Information about participating food vendors, performers, guests, schedule and other details will be posted on the event’s website as it nears.

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

Picnic with the Pops: “Dancing in the Streets: The Music of Motown” 

Aug. 13 • The Meadow at Keeneland, 4201 Versailles Road.

Picnic with the Pops has been a favorite summer event in Lexington for more than 30 years. Each year, the Lexington Philharmonic teams up with a special guest performer to present 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.) A table-decorating contest is an annual highlight of the event.

This year’s show will be “Dancing in the Streets: The Music of Motown,” a celebration of an iconic era of music featuring hits from artists like Marvin Gaye, The Temptations, The Four Tops, Stevie Wonder and more. Tickets will go on sale in July. 

Woodland Art Fair 

Aug. 20-21 (10 a.m.-6 p.m. Saturday; 10 a.m.-5 p.m. Sunday). Woodland Park, 601 E. High Street.

The Woodland Art Fair, produced by the Lexington Art League and Lexington Parks and Recreation, has been one of Lexington’s most celebrated cultural events for more than 40 years. Featuring dozens of artists and makers selling unique, handcrafted items ranging from ceramics and wood art to jewelry and photographs, the event brings thousands of attendees together in the park each year. Food trucks and beer vendors will also be on-site.

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