Spotlight of the Week: Orlando Pena

Orlando Pena is a singer-songwriter based in the Milwaukee area. He not only performs solo but also with the Americana-folk band The Midnight Purchase; their EP “The National Sessions” came out in 2019. Think of his music like a warm cup of apple cider next to a fire in a cozy log cabin.

ME: Alright Orlando, first things first. How did you get involved with Wisconsin Music Ventures?

ORLANDO: I had seen when they started doing the open mics at Bottle House 42. Bruce Humphries was the host and I had seen him post around some of the local Wisconsin music group pages on Facebook just looking for people to come out and play it because it was still brand new, so I think I just liked the post he had made and he just messaged me right away and asked me if I wanted to be their first featured artist. It didn’t work out because I think I had a show that day but he told me to come next week. So I was the featured artist the second week and Allison was there, so we just got to talking, and she invited me to apply for Wisconsin Music Ventures after that.

ME: Awesome, really cool! Beyond that, I’ve got some Wisconsin-themed questions for you.

ORLANDO: Oh boy, as I wear my Bears hat (laughs).

ME: What do you think is the most beautiful part of Wisconsin?

ORLANDO: Ah, there’s so many good ones. I honestly need to get out and travel more. But I used to go fishing in Boulder Junction every summer, almost by the UP, back in high school with my friend’s family. It was like a guys’ trip he would go on with his uncles and his grandpa and his cousins, and they’d start inviting me because I was raised by my mother only. So that’s always stuck out to me, just how crystal clear the night sky is up there; we used to sit out on the docks and just stare up at the sky. Otherwise, more recently I played Driftless Books and Music in Viroqua, and I had no idea that western Wisconsin is pretty rocky; it’s a lot different of a landscape from here but it’s beautiful. That whole weekend I had to drive out there by myself and the whole drive in was so weird, like wondering where I was going. The community in Viroqua was so cool; they have a community garden that supplies food for everyone and everyone’s really nice. I’ve always wanted to go back there.

ME: Good places for me to keep in mind! I’m trying to get more out of town too and invest in the beauty of our state, because there’s a lot of it.

ORLANDO: We’re so lucky dude.

ME: Do you like camping?

ORLANDO: Oh I love camping and hiking. I used to go camping a bunch alone; I would just take my dog, and I’m kind of into bushcraft, like wilderness survival stuff. So I’d just go out for weekends at a time and figure it out, like making chairs and tying knots (laughs).

ME: Yeah man, there’s a whole subculture of that.

ORLANDO: It’s so much fun to get back into simple living.

ME: This next one’s a bit of a two-parter. What’s your favorite Wisconsin brewery for the beer?

ORLANDO: Damn, that’s also a tough one. They’re all really good. My go-to beer anywhere is a Riverwest Stein, so that’s Lakefront. I mean all their stuff is pretty good but anywhere I go I just really like that beer. I like MKE Brewing too.

ME: What’s your favorite Wisconsin brewery to play at?

ORLANDO: I really miss the Pabst Taproom. That was just an incredible space for anybody to get to play; it was like an old church and it sounded incredible. I’ve been talking with Central Waters about their plans for music there coming up, so I was excited to hear that they were coming to town and doing something with that space. You just felt so good on that stage with a full light show and smoke.

ME: I do miss that spot. Sadly we lost it to the pandemic. I saw you’ve played that place Raised Grain; what’s that one like?

ORLANDO: Yeah, they’re awesome! Rex is the manager out there. That’s in Waukesha kind of off 164. They actually have some great beers too and they do music every Wednesday and some Saturdays. They had just gotten a patio set up outside for the summer and were hosting full bands. They have a lot of great artists go through there and have a good staff and crew.

ME: Good to know. My last question for you is, what are you working on now?

ORLANDO: Right now we’re going to be slowing down on the gigging a little bit. I still gig solo as my job so I have to keep doing that, but with the band we’re slowing down and actually trying out drummers at the moment. I actually spent most of this morning working on tour for the spring to go down through Tennessee and Asheville. Our goal this winter is to just record so we can shop around that new music on that tour. That’s about it.

ME: Very exciting. What are your next gigs?

ORLANDO: This Saturday I’m at Jose’s Blue Sombrero in Wauwatosa. Then I’ll be at another new spot, Bad Moon Saloon, on Wednesday of next week. That’s right around the corner from my house here in Bay View. It’s a biker bar spot. I was actually in there last night seeing Matt Tyner play and was doing my homework seeing what the room sounded like. It was a lot of fun!

Songwriter | Orlando PeΓ±a (orlandopena.com)


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