A comprehensive look at upcoming festivals and other big cultural events, as featured in our 2025 Fall Arts Issue.
Click the following links for more 2025 Fall Arts listings: Visual Arts • Theatre & Performance • Dance • Literary & Film Events
Lexington Roots & Heritage Festival
Sept. 5-7 • Elm Tree Lane • www.rootsfestky.com
For over 30 years the Roots and Heritage Festival has been a pinnacle of regional diversity providing entertainment and education for all ages. Multiple blocks along Elm Tree Lane between Fourth and Short Streets are blocked off for the annual event that celebrates cultural diversity in Lexington with food and retail vendors, live music, parades and family activities.
St. Andrew Orthodox Church Annual Heritage Festival
Sept. 6-7 (Sat., 12-8 p.m.; Sun., 12-5 p.m.) St. Andrew Orthodox Church, 1136 Higbee Mill Road • www.standrewlexington.org
For more than 30 years, St. Andrew Orthodox Church has celebrated the rich and widely varied cultural heritage of its parish community with this two-day event, which features an assortment of international foods like falafel, gyros and baklava, as well as entertainment and church tours.
National Endowment for the Arts Jazz Master first-year Kenny Garrett is among the performers for Equinox Jazz Festival, a first-year event taking place Sept. 17-22. Photo furnished
Equinox Jazz Festival
Sept. 17-22 • The Kentucky Theatre, 200 Main St. • www.originsjazz.org/equinox-jazz-festival
Presented by Origins Jazz Series, this five-day celebration will join tradition and innovation, honoring jazz’s rich legacy and its boundless future. From intimate showcases to electrifying headliner performances, this festival will embody the spirit that has driven the genre forward for over a century.
The curated lineup includes a mix of legends and rising stars, from National Endowment for the Arts Jazz Master Kenny Garrett and Jazz at Lincoln Center Orchestra veteran Camille Thurman to Rose Colella with the Osland-Dailey Jazztet and Kandace Springs. Visit the event website for the full lineup and other details.
Christ the King Oktoberfest
Sept. 19-20 • Cathedral of Christ the King, 299 Colony Blvd. • www.ctkoktoberfest.com
This annual Oktoberfest celebration features fun for all ages including live music, German food, kids’ games, arts and crafts, inflatables and bingo.
Festival Latino de Lexington
Sept. 19-20 • Robert F. Stephens Courthouse Plaza, 120 N. Limestone • lexingtonky.gov/festival-latino-de-lexington
Celebrate Latin American art and culture in the heart of downtown Lexington at this two-day festival, presented by Lexington Parks & Recreation and the Foundation for Latin American and Latino Culture and Arts. Attendees can enjoy live music, dance, visual arts and authentic cuisine.
Lexington Pizza Week
Sept. 22-25 • www.lexingtonpizzaweek.com
Brought to you by Smiley Pete Publishing — the same folks behind Lexington Burger Week, Lexington Taco Week and this very publication — Lexington’s biggest pizza party will feature dozens of participating restaurants, each offering special pies for $10 (either a 10-inch pie or two extra-large slices). Participants are encouraged to check out as many locations as their heart desires throughout the week, checking in with the Lexington Pizza Week app to be eligible for prizes. See the website (or insert in this magazine!) as the event nears for more details on participating locations and featured pizzas.
Bourbon & Belonging
Oct. 3-5 • Various locations • www.bourbonandbelonging.com
For the second year in a row, Queer Kentucky, a Louisville-founded nonprofit focused on uplifting LGBTQ+ lives through storytelling, culture and action, is presenting “Bourbon & Belonging: Kentucky’s Queer Bourbon Week,” the first LGBTQ+ inclusive bourbon festival in the country. The three-day event will include tastings, tours, pool parties, drag brunches and art events within several cities across the state.
Tree Week
Oct. 10-19 • Various locations • ufi.ca.uky.edu/treeweek
Produced by The Urban Forest Initiative, this annual celebration is designed to foster an appreciation of trees and green spaces in Lexington and other communities throughout Kentucky. Participants can enjoy tree walks, tours and hikes, educational programming for youth and adults, art projects and exhibitions, and yoga.
Scarefest Horror & Paranormal Convention
Oct. 17-19 • Central Bank Center, 430 West Vine St. • www.thescarefest.com
The nation’s largest horror and paranormal convention, Scarefest celebrates its 16th installment this year with dozens of exhibits, vendors, seminars, and meet-and-greets and photo-ops with celebrities from the horror, sci-fi or paranormal genre. This year, special guests include actors from “A Nightmare on Elm Street,” “Scream,” and “Halloween.” Visit the event website for the full lineup, event times and other details.
Lexington Bourbon Week
Nov. 6-15 • www.lexingtonbourbonweek.com
For Lexington Bourbon Week dozens of participating restaurants and bars will offer special bourbon-centric cocktails that aren’t normally on the menu, utilizing creative ingredients designed to impress any palate. See the website as the event nears for more details on participating locations, the featured cocktails, and ways to participate. Lexington Bourbon Week is produced by Smiley Pete Publishing, the producers of Lexington Burger Week, Lexington Pizza Week, Lexington Taco Week, and this very publication.
WORTH THE DRIVE
Bourbon & Beyond
Sept. 11-14 • Highland Festival Grounds at Kentucky Expo Center, Louisville • bourbonandbeyond.com
This large-scale music festival returns to Louisville with an extensive and eclectic lineup straddling genres from pop and indie to jam and Americana, as well as a bevy of experiences that highlight Kentucky’s signature bourbon and culinary culture. Headlining artists for this four-day festival include Noah Kahan, Phish, Jack White and The Lumineers, with over 100 additional acts. Now in its seventh year, this year's event features a handful of changes – click here to read more!
Louder Than Life
Sept 18-21 • Highland Festival Grounds at Kentucky Expo Center, Louisville • louderthanlifefestival.com
At this four-day rock and metal festival, fans can expect 160+ bands across six stages featuring heavy hitters like Slayer, Deftones, Avenged Sevenfold, Bring Me the Horizon, Rob Zombie, Sleep Token and Bad Omens. Now in its seventh year, this year's event features a handful of changes – click here to read more!
Black Mountain Jamboree
Oct. 3-4 • Hidden Ridge Camping, Monticello • www.blackmountainjamboree.com
Located on a private property-turned campground near Lake Cumberland, Black Mountain Jamboree is campout music festival highlighting 14 local and regional bands. This year’s lineup includes Magnolia Boulevard, Paul McDonald & the Morning Doves, Dee oh Gee and Ruen Brothers. Additional festival experiences include yoga, live painting, a cold plunge and bonfire experience.
The Afro-Cuban funk band Cimafunk is among the headliners at this year’s Moonshiner’s Ball, taking place Oct. 9-12 in Livingston, Ky. Photo furnished
The Moonshiner’s Ball
Oct. 9-12 • Rockcastle Riverside, Livingston, Kentucky • www.themoonshinersball.com
Now in its eleventh year, regional music festival The Moonshiner’s Ball returns to the Rockcastle County venue Rockcastle Riverside for a weekend of music, camping and fun for all ages this fall. Following the unofficial tagline “folk by day, funk by night,” the festival features a diverse and robust music lineup with headliners like Margo Price, Cimafunk and The Brothers Comatose. Tickets, the full line-up, and more information is available at the event website.