Your Guide To Lexington's Upcoming Cultural Festivals

Peter Chawaga


Lexington is renowned for its diverse range of residents, who have found ways to express their unique perspectives and celebrate their communities through the city’s array of infamous cultural festivals.

But as the spread of COVID-19 forced the cancellation and rescheduling of many of these annual favorites, residents have been participating virtually or keeping their excitement at bay until live events returned. With fall around the corner, TOPS is pleased to report that many of Lexington’s most engaging cultural events are expecting to come back, with a renewed appreciation for the importance of live celebration and lessons learned during the hiatus.

Below, we’ve rounded up the latest plans for the city’s most popular festivals and gathered firsthand perspectives on how organizers were able to remain optimistic, flexible, and committed to celebrating culture.


Though organizers warn that the 45th annual Woodland Art Fair could be cancelled at any point between this writing and its planned date, the event is scheduled to take place from August 21 to August 22.

“In the hope of hosting a scaled-down, socially-distanced version of the Woodland Art Fair we are making tentative preparations,” the event website reads. “We have developed a plan that honors the spirit and tradition of the Woodland Art Fair, but allows us to provide artist opportunities and community participation in a safe, COVID-19 friendly way.”

Among those potential changes to the event could be a reduced number of booths, safety guidelines for vendors and patrons, controlled access with health screenings, staggered attendance, a mask requirement, and additional handwashing and sanitation stations.

One thing that would not change is the event’s award-winning celebrations of artists and the unique creative culture of Central Kentucky.


For the 32nd year, Lexington’s annual Roots & Heritage Festival will be held to celebrate African-American culture and achievement. Despite initially planning to hold the event virtually, organizers have determined that it can and will be held in person, from September 10 to 12, on Elm Tree Lane between Short Street and Fourth Street, with two stages of entertainment; information, food and commercial vendors; a parade; and a gospel program.

“The festival began in 1989 [and is] held in the historic East End-Deweese Street corridor, which was a thriving area of black-owned businesses,” Kimberly H. Baird, the festival chair since 2005, told TOPS. “People from around the country come together to enjoy the events of the festival, and families plan reunions around it.”

But, like the city’s other annual live events, festival organizers were forced to reconsider how the Roots & Heritage Festival could take place in 2021. Baird said that the group was inundated with requests for dates and vendor information from people assuming the festival would be held live, making it clear that the organizers had to find a way to host an in-person, yet safe, festival for the community.

“Having a live festival for any group is important right now as people are struggling with isolation and loneliness, depression, lack of social interaction, modified activities and trying to find a new normal,” Baird said. “Equally as

important is the need for cultural festivals. In the current climate on race relations in the country, and particularly in Lexington, providing as many cultural and celebratory events to educate the community about each other will serve to foster inclusion and understanding and strengthen relationships.”

A silver lining among that uncertainty is that the festival committee now hopes to include some of the virtual offerings it had planned, expanding its programming during the month and providing new avenues for those in Lexington and beyond to participate.


After having little choice but to cancel its annual St. Patrick’s Day celebrations in 2020 and 2021, the Bluegrass Irish Society has announced that it will be hosting a Halfway To St. Patrick’s Day mini-festival on September 19 at the Moondance Amphitheater at 1152 Monarch Street. This celebration will host bands, Irish dance schools, and other performances to spotlight Irish culture as the group prepares for a hopeful return of the full-fledged St. Patrick’s Parade And Festival on March 12, 2022.

“The Lexington St. Patrick’s Parade is one of the longest-running civic events in the City of Lexington, and we’re eager to bring it back,” said Megan Moloney, the president of the Bluegrass Irish Society. “We’re hopeful that 2022 will be when we can resume.”

The St. Patrick’s Parade And Festival was one of the first major events in Lexington to cancel in 2020 because of the COVID-19 pandemic, and it was disappointing to many, but the organizers remain steadfast that protecting the community is the number one priority.

“While holding our event is something to which we all look forward, keeping our community safe and making decisions that protect our fellow Lexingtonians is much more important,” Moloney said.

With the upcoming Halfway event, it appears the organizers have found a way to continue cultural celebration while maintaining that safety at the same time.


After hosting a “LexPride Live” event broadcasted live from the Kentucky Theater last year, the Lexington Pride Festival is scheduled to return on September 25 at the Robert F. Stephens Courthouse Plaza at 120 North Limestone.

“Attendees should expect a fun, meaningful community event that empowers and celebrates the intersectional lives of LGBTQIA+ Kentuckians,” explained Carmen Wampler-Collins, the executive director of festival organizer Pride Community Services Organization. “There will be music and performances, speakers, diverse vendors, and food and drink. The hallmark of the festival will be an accepting, diverse atmosphere where LGBTQIA+ people are safe to be who they are and love who they love.”

The Lexington Pride Festival is critical in providing visibility for the LGBTQIA+ community and the issues it faces, for giving its community members a feeling of comfort in public to express themselves and for providing a positive financial impact to local LGBTQIA+-owned businesses as well as the Pride Community Services Organization’s Pride Center in Lexington.

While many of these crucial services were provided remotely last year, the return of the in-person event is certainly something worth celebrating.

“There was a lot of sadness and grief about not being able to hold our traditional festival,” Wampler-Collins said. “Hearing from multiple people about what the festival means to them has underlined the importance of the event for us, and the need to get back to it as soon as possible. Lexington’s festivals seem to be a tradition for folks — an important way of marking time and celebrating and making connections.”

The festival will also be incorporating some of the lessons learned from its pivot last year. Organizers have a goal of broadcasting a portion of the festival live, so that more people can participate virtually. They are also working to make the layout of the in-person festival more accessible and less crowded, and to incorporate a more streamlined approach to buying drinks. And finally, moving the celebration from June to September should offer more comfortable temperatures for attendees.


Festival Latino De Lexington, an annual celebration of Latinx culture presented by the Foundation for Latin American and [email protected] Culture and Arts (FLACA), has announced that its 2021 edition will be held from October 15 to October 16 at the Robert F. Stephens Courthouse Plaza at 120 North Limestone.

Over two decades, the festival has welcomed thousands of attendees, featuring authentic cuisine, art vendors, youth activities, and cultural expression unique to many of the countries of Latin America. It has been the annual focal point for FLACA’s mission to encourage public awareness, education, and participation around Latin American culture.

“For FLACA, it is fundamental to promote, foster and preserve the culture, traditions, and languages of our Latin American and [email protected] heritage,” according to the FLACA website. “The highlight of FLACA’s collaboration with the community, the local government ... and other organizations is the Festival Latino of Lexington. With the motto, ‘many cultures ... one city,’ this festival represents the spirit of FLACA’s mission.”

Check Out...

This is by no means a definitive guide to the vibrant culture that will be celebrated around town in coming months!

Check out the TOPS Community Calendar for the latest events happening around town:


Two days of music, Bourbon, and Kentucky food at Keeneland. August 28-29


Head to Woodland Park for an enchanting evening of entertainment. August 5-8


Live music and awesome mingling in Tandy Park. Thursdays through October


Tuesday evenings in Ecton Park get jazzy. Through August 17


Watch Honeychild live at Moondance Amphitheater. August 27


Enjoy live music on Southland Drive. August 19 & 26


Celebrate live music with the Lexington Philharmonic. August 14-15