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Our Saturday Guide To The Must-See Artists At The 2021 Railbird Festival In Lexington!

Back in 2019, the grounds at Keeneland were invaded by music lovers from all over the United States. Their pilgrimage led them to the heart of the Bluegrass where Lexington finally hosted the music festival it deserves. You can read our recap and view our photos here.  There were many highlights that year, and the momentum heading into 2020 was obvious and mighty. Unfortunately, a pandemic interrupted all of our lives, but I’m happy to say that the Railbird Festival at Keeneland is back! After a year off due to the pandemic, live music is finally returning to the beautiful grounds at Keeneland and we’ve put together a list of the artists that you just have to see.

Some tough decisions will definitely have to be made over the two-day festival. There’s just simply too much real estate to cover to see every act on all three stages, but hopefully we can help you sift and sort through the list and help you maximize your dollar.

Railbird is booked and managed by the same production company that is behind The Bonnaroo Festival and the Forecastle Festival in Louisville. AC Entertainment doesn’t have their finger on the pulse of music, they are the pulse. You can trust that any festival or venue that AC Entertainment runs, is worth your efforts to attend.

Let’s kick this list off with a local. Mr. Nicholas Jamerson will be the first notes heard in 2021. He takes the Burl stage at 1:30 and will bring his signature sound to life. Jamerson has recently reunited with his buddy Kris Bentley as Sundy Best, but on Saturday you’ll get the opportunity to hear a lot of Nicholas’s solo work, that I feel is vastly underrated.

At 2:15, grab your kleenex and head over to the Limestone stage where John Moreland will provide one of the more moving performances that Friday will provide. Mr. Moreland is an absolute must for anyone that hasn’t experienced his songs. He will make you feel emotions that you didn’t even realize you needed to experience.

The first, and perhaps the toughest decision of Friday, will be between Sierra Ferrell and Sarah Jarosz. I absolutely adore both young ladies, BUT seeing Sierra Ferrell on the smaller Burl stage at 2:45 wins this one for us. Why? Because The Burl stage is a much more intimate setting, and as the world gets their first taste of the true artist that Sierra is, you’ll be thankful for witnessing her on the smaller stage. No one, and I mean no one, sounds like Sierra Ferrell.

I have recently become quite the fan of Joy Oladokun and I plan on catching the first part of her set on the Limestone stage at 3:45, but on a personal note, Magnolia Boulevard will take the Burl stage at 4 pm. Based here in Lexington, Magnolia Boulevard has drawn comparisons to folks like Bonnie Raitt and Tedeschi Trucks, which is fair, but I say just enjoy Magnolia Boulevard for who they are. You won’t be disappointed.

Next, you’ll want to find yourself at the Elkhorn stage where Margo Price takes the reins at 4:30. Margo is one of the more important voices in music these days. She’s got a lot to say, and you’ll definitely be glad you listened. Price also has a lot of connections to Kentucky music. As Sturgill Simpson was once her guitarist. Margo then brought Tyler Childers to the Ryman in Nashville for his debut there. Then this Fall, Childers is taking Margo for her debut at Red Rocks. Small world huh?

At 5:30, over at the Limestone stage, you do not want to miss Black Pumas. I am a huge fan of the Black Pumas soulful style and their performance is in my personal top three for Saturday’s performances. I’m actually listening to “OCT 33 – A Colors Show” as I’m typing this section of the article, so go ahead and enjoy it yourselves below.

Midland is the one artist, if I’m completely honest here, that really doesn’t seem to fit the crowd that Railbird draws. Well, at least the crowd that came in 2019. Midland plays at 6:30 at the Elkhorn stage. I do enjoy quite a few of their songs, and I’m all about helping folks expand their musical palette, so I’ll definitely be catching a lot of their set, and I will use their set as a barometer for the future.

BUT, by the streaming numbers, Briston Maroney is the most popular artist to take the Burl stage on Friday. So choosing to see his set at 6:30 instead, is a perfectly acceptable option. Maroney’s “Caroline” has been in heavy rotation for me since my first listen. Check it out below!

At 7:15, over on the Limestone stage, one of my personal favorite artists takes the stage. Mr. Leon Bridges is absolutely fantastic and his set is one that I’m anxiously awaiting. I love everything this young man does. If you’re new to his music, he will make you a fan within the first three notes you hear.

The Elkhorn stage at 8:15 will be one of the biggest crowds of Friday. Why? Because Billy Strings will be burning the stage to the ground. Billy is one of the most talented folks on our planet and his collaborations are a testament to that fact. He has songs with Luke Combs, RMR, Sierra Ferrell, Don Julin, Del McCoury and has even been spotted with Post Malone. Having said that, if you miss Billy Strings, you will kick yourself…a lot. Btw, in 2019, Billy played the Burl stage. That’s why you best not overlook any artist playing over there.

Ending Friday night on the Limestone stage at 9:15 is My Morning Jacket. Born and bred in Louisville, Kentucky, MMJ is a global musical juggernaut and is a can’t miss artist. Especially if you’re a Kentuckian. Some artists are incredibly hard to describe, in the case of My Morning Jacket, I have yet to see a truly accurate description in 18-20 years. So there’s no way I’m going to be able to do so here. I will throw out some adjectives to try and help ya out. Trippy, spaced-out, calm, and melodic. Kinda like the Kentucky fried version of Pink Floyd. I suspect Keeneland will have quite the familiar odor after Billy Strings and My Morning Jacket on Saturday night. Lol

The Railbird Festival is officially sold-out, so hopefully, you got your tickets already. There are new rules in place before you’re allowed to enter Railbird. I’ll leave you with the official statement from the Festival’s Facebook.

The safety of our patrons and our staff is our number one priority. As such, a full COVID-19 vaccination or negative COVID-19 test results will be required to attend Railbird 2021.

For patrons who are not fully vaccinated, a negative COVID-19 test result must be obtained within 72 hours (3 days) of first day attending Railbird.