The Road to Red Bluff Fest: Ben Benefield of Winston Ramble May 2, 2025 14:59

Interview by Jordan Kirkland: Live & Listen

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Red Bluff Music & Arts Festival represents one of Montgomery, Alabama's latest annual celebrations, and we're counting down the days to the third installment on May 16th - May 18th. The 3rd annual festival will be held at Red Bluff Bar (Friday) and Riverwalk Amphitheater (Saturday & Sunday), featuring a wide variety of national and regional acts across a diverse musical spectrum.

As we prepare for this year's festival, we're catching up with each of this year's performers to gain and share some additional insight for anyone planning to attend the festival. The series continues today with Ben Benefield, the frontman (guitar/vocals) of Winston Ramble. These guys have been crushing the Alabama music scene for over a decade now, and you can always count on a Ramble set to deliver. 

While the band's lineup has evolved over the years, there is no doubt that the current roster is their strongest to date. As anyone who attended their recent WorkPlay show will attest, the is firing on all cylinders (to no one's surprise). Ben Benefield (guitar/vocals), Justin Oliver (mandolin/harmonica), Taylor Goodwin (lead guitar), Ryan Brown (bass), and AJ Covey (drums) continue to prove that Winston Ramble is amongst the all-time great Alabama bands.

Check out our conversation with Ben below, and make sure to head over to your preferred steaming platform for all of the band's latest releases. If you're a fan of good, ole-fashioned rock-n-roll, you will not want to miss the Saturday Ramble at Riverwalk Amphitheater on May 17th.

From what I understand, Winston Ramble originated from the band’s deep roots in Winston County, and ultimately came to life in Birmingham. You guys have been going strong for at least a decade. Can you tell me a little more about how the band came to life?

Ben: Justin and I met and started playing music together in high school. He had already been living in Birmingham for a few years when I came down to try and play some actual paying gigs. We were playing as a duo and had already came up with the name Winston Ramble, but we wanted to expand the sound. We invited the other guys from our high school friend group ,that also played some music to jam. It became what it became. That sound was there from the start. 

Then when COVID shut everything down, touring and shows stopped, everybody kinda started slowing down and getting married or had kids. Things changed. Justin and I knew we wanted to keep going, no matter what, but it had to be with the right people. Somehow, when we would need someone to fill in for a gig, we would have the same name in mind. Then that person ended up in the band. When an original member would start phasing out of the band, the first name on all our lists for replacement wound up being the new member. We got super lucky getting Taylor, AJ and Ryan to join the team.

The band has been a key staple in the Alabama music scene for many years now. At what point did it become apparent that you guys had something really special?

Ben: We just play stuff we like to hear. Pretty much any song is up for grabs with us. I’m honestly amazed people still come out like they do. It’s like a family reunion at this point, a big chunk of people at our shows have been coming for a while so people are hugging and singing, it’s really special to see. When we first started touring out west and to the northeast and these “far-away” places and seeing people from Bham and northwest Alabama, I knew something special was happening then and that we didn’t have just “average” fans. They really make the whole thing special.

Over the past year, you’ve released a series of EPs simply titled ‘Heaters’ (Vol. 1-3). These have featured previously released ramble tunes, as well as covers. What was the general idea behind this concept? Can we expect more Heaters to come in 2025?

Ben: There are some covers that we play that we've done enough times that they can sometimes feel like our own songs in the sense that our sensibilities and camaraderie are on full display. In that spirit we decided to record some of the tunes that have really become quintessential "Ramble" tunes. There are also some Ramble originals that we wanted to re-record with the "new" iteration of the band members and it felt natural to slip those in alongside the Heaters covers that we wanted to record. Certainly more heat to come.

I know the past decade has produced countless epic memories, both in Birmingham and out on the road. Can you share a few of the top highlights that come to mind?

Ben: The last two shows we played in Birmingham were really special. In November, we did an acoustic set that featured some awesome bust-outs, like "Rooster" (Alice in Chains) and "Ooo La La" (The Faces), as well as our version of Don Henley's "Dirty Laundry," which we dovetailed into our song "Dreams". Earlier this year, we did a full Rolling Stones set at Workplay, which was a really fun collection of music to put together for us and was super memorable. 

Sometime in 2022, we were going through some growing pains and had to pare down to a trio for a run of shows through North Carolina and Virginia. We almost canceled the run altogether, but decided to just get out there with an acoustic guitar, a mandolin, and a tiny drum set. Somehow that combination of instruments worked really well together, and it ended up being really special (until our van died in West Virginia).

The Ramble catalog has always been as strong as any Alabama band, in my opinion. Can we expect any new debuts in 2025? Any details you can share?

Ben: Thanks man! We definitely are trying to do something different every time we get to go into the studio. I think we’ve finally got a pretty good handle on what we can do in there in that setting and what kind of sound we really wanna make. Our last few EP releases (“Heaters” 1-3) and single (“Whole New Way”) was some of the easiest and most fun I’ve personally ever had in the studio. We’re really focused now when we’re all together. We are all always sharing new ideas and things with each other for new material so, without giving too much away, we are definitely hoping and shooting for a proper release this year of some new original material.

The band returns to Montgomery for Red Bluff Fest at Riverwalk Amphitheater on Saturday 5/17. What should those in attendance expect to see and hear from Winston Ramble?

Ben: Good, ole-fashioned rock-n-roll!