Milwaukee Summerfest 2026 Kicked This Summer Off With A Bang

milwaukee’s summerfest 2026

Welcome back /CW Fam. You know it wouldn’t be right if I didn’t begin by asking each of you a question. That question being, what comes to mind when you are thinking of the best way to shift your focus to positivity and a good time during challenging times? Is it a vacation? A vibrant party? Or is it a day of rest when you do absolutely, and I mean positively nothing at all? [Could you tell the last one was my favorite answer?] This question instantly clouded my mind when thinking of the current climate of not only our city, Milwaukee, but across the entire nation.

From the skyrocket price increases in essential items such as groceries and gas, the decrease in flexibility in the job market, and the emotional state of our country, much of Milwaukee’s morale has been at one of its lowest points. Luckily, the city can always count on the summer season to bring the heat by opening the doors to innocent family fun and an energetic atmosphere. For nearly sixty years, the city’s lively annual music festival, Summerfest, never fails in kicking off a summer of endless entertainment, community engagement, and a love for food like no other. I knew this year would be no different when it came to the impact it would have on Milwaukee, which is why I made the Summerfest grounds my mission for the past few weekends.

milwaukee’s summerfest 2026

The lively festival made its annual debut on Thursday, June 18th at 6:00 pm as the official opening ceremony began. The theme around the opening ceremony was to celebrate and elevate the visibility and knowledge of the national holiday, Juneteenth. The bold and bright display of colors, patterns, and textures was only the beginning. Many patrons expressed to me that the opening ceremony never fails at making them feel not only heard but seen, most importantly. Summerfest recognized the fabulous recipients of Northcott Neighborhood House’s Juneteenth scholarship pageant. Summerfest is honored to support this program, which showcases leadership and achievement within the Milwaukee community, through a scholarship donation. This year’s recipients were:

Mister Juneteenth: Jace White

Miss.Juneteenth: Gianna Cooks

Little Miss.Juneteenth: Ava Garry

Little Mister Juneteenth: Michael Terry Jr.

The elaborate crowning of these four extraordinary Milwaukee youth laid the perfect velvet red carpet for the night's entertainment. It created a fiery energy that made those in the crowd anticipate how the rest of the night would flow. R&B legend and talented songwriter Charlie Wilson serenaded the crowd, creating a grown and sexy sound that filled the BMO Pavilion stage. The Summerfest grounds became the perfect place to devour your favorite guilty pleasure, relax on a lounge chair, and take in the breathtaking waterfront as Charlie Wilson was bringing down the house. The 3,700-foot-long strip was full of close-knit families, flirty couples, and confident solo adventure seekers who explored the shops, restaurants, and rides throughout the night. Although it seemed like everyone and their mama [and their mama’s mama] was there, everyone on night 1 was on the same accord of being on their best behavior and just enjoying the calmness of Milwaukee while also turning up in their own way.

JUNETEENTH PARADE TALENT DANCING

To be completely honest /CW fam, I didn’t know what to expect as being on the Summerfest grounds several days back-to-back as a journalist, but I was relieved when it clicked that repetition and moments moving in slow-motion would not be a thing. Every day, I was enamored with how interactive and spontaneous each day brought to my attention. Between the 2s, FREEs, and 3s basketball shooting competition, free Latin dance classes along with giveaways presented by Aurora Healthcare, and Potawatomi’s big win raffle, where 5 people were given the chance to win $1 million, I was constantly entertained and shown different sides of the city I had never quite immersed myself in. It was as if everybody in attendance had been in the same group chat prior to Summerfest 2026 starting, and the goal remained the same from start to finish: have a ball and leave all your troubles at the door! Day 1 definitely set the tone for one of the most anticipated, high-volume, and interactive years Summerfest grounds has ever seen!

milwaukee’s summerfest 2026

Not only was this the place to be if you were searching high and low for a jam-packed party with music to the max volume, fresh off the grill barbecue food, and several unique chances to win some BIG items, but it was pivotal for entrepreneurs as well. It didn’t matter if I was walking towards the Miller Lite stage to see the legendary Sean Paul perform or strut to the other side of the grounds to get a hot and sizzling slice of Saz’s pizza; vendors were covering every corner of Summerfest! What surprised me was the versatility of all of the different items that were being sold. From puzzles made of pictures from your camera roll, authentic Puerto Rican jewelry, henna tattoos, personalized and MKE-inspired license plates, to dreamcatchers as big as a beach ball, the creative entrepreneurs were showing up and showing out! Not only did they gain much visibility and business, but the interactions I witnessed them have with patrons were nothing but wholesome and pure appreciation for one another. If you are an entrepreneur yourself, apply next year to be a vendor and witness the magic for yourself.

R&B ARTIST, ELLA MAI PERFORMING AT MILWAUKEE’S SUMMERFEST 2026

Although the sense of community, slammin’ food, and vibrational energy everybody had playing games and exploring the different aspects of Summerfest was refreshing to see, it has remained crystal clear that the #1 thing wanted by patrons is to vibe out to their favorite tunes. BABBBYYYY this year’s lineup had the city [yes, including you too] hyped to be in the crowd of countless performers. Tyrese, Charlie Wilson, Jelly Roll, The Roots, Common, Don Tolliver, Flo Rida, Jeremih, and DJ Jazzy Jeff are just the tip of the iceberg when it comes to the extended list of heavy hitters that were booked to be the highly anticipated lineup for Milwaukee Summerfest 2026! No matter if it was a youngin’ who just hit puberty or one of the aunties whose been here for a while, every crowd was singing the lyrics from the top of their lungs. However, I have to confess that I strongly believe the artist that rocked the house the hardest was Ella Mai on July 2nd at the BMO Pavilion stage! She had everybody in the building boo’d up and trippin’ off each song she performed.

R&B ARTIST, ELLA MAI PERFORMING AT MILWAUKEE’S SUMMERFEST 2026

My girl Ella Mai ate and left not a single crumb left! Her performance stood out to not only to me but to the Summerfest crew and crowd. She did something no other artist had took the risk of doing this year. In between giving us passionate and strong vocals and a boom bow boom on the choreography, the energetic performer invited select fans onto the stage to show out their talents and personalities. This stole the hearts of the crowd and had everybody ready for even more! Many different people in the crowd were singing their hearts out along with Ella all night long but only a few had the courage to confidently walk onto the stage, one of them being Wisconsin artist, Troy Tyler. Check out my interview with him below to get the inside scoop of how he felt right after the moment happened!

MILWAUKEE’S SUMMERFEST 2026

MILWAUKEE’S SUMMERFEST 2026

My first year attending Summerfest as an on-site journalist was eye-opening, educational, and exciting! I learned and witnessed so many of the ins- and outs I never saw going as a patron. Who knew how much logistics, time, and work went into the layout of the grounds as well as the performances. It is definitely worth attending next year if you couldn’t make it this year. Everyone was proud to represent the city of Milwaukee and have a good time while doing so whenever I got into interview mode!Stay tuned for the interviews below I did with DJ Girl Next Door, Troy Tyler, and Lilo Allen to get their take on what it felt like being a part of Milwaukee Summerfest 2026!

Desriana Gilbert/ Entertainment & Social Journalist for CW

Huey V - “After The Deal” [SINGLE + Press Interview w/ CopyWrite Mag]

Milwaukee continues to make its mark in pockets of creative and social niches, whether it be politics or music, our presence is becoming more known to the world. As the wave of the rising talents of Milwaukee continues to flow, more names get added to the list of young people to look out for. Post the drop of his newest single “After The Deal”, Memphis Bleek’s Warehouse Music Group's (WHMG) latest signee Huey V gave us a moment and shared with us his journey leading up to this drop. 

 /CW: What was your upbringing in Milwaukee? What was your family like, where did you go to school?

HV: I'm a North Side baby, low tres, low tres. Most of my family grew up on 32nd and Galena but we spent a whole bunch of time on 33rd too. Outside of that I kinda lowkey moved all around the north side. I lived on 41st and Congress for a good minute, I wanna say like 7 years… I didn’t really fuck with down town until I turned 16. It was just the North Side, the beach and Mayfair.

/CW: So the North Side was just your little world growing up. You didn't know anything outside of that.

HV: …That was my whole world at that time before I got a car: I'm a youngin, youngin still. If I’m not on the city bus I'm walking, if I'm not walkin I’m on the bike..so I was definitely just exploring [the North Side]. That was the biggest shit to me at the time. I was like 13-14, just discovering the world on my own… 

/CW: So anywhere you needed to go you pretty much got there.. What made you get to that point where you're like ‘okay downtown is right there why not just go? Why not see what's over there?’ Was it the music, your artistry? 

HV: ..There was a poetry tournament..if I'm correct it was at The Grand... It was my first year on a poetry team and they ended up taking us down there because we had a [competition] with Ronald Reagan High school. That was my first competition..that was my first time seeing what it looked like; white people in suits and shit like that. That wasn't really a common thing for me.  

/CW: Did you have a lot of mentorship growing up or was it not until you got older and started taking charge of your own life that you decided ‘I need more discipline with whatever I'm doing and need to seek out that mentorship?’

HV: As a youngin you're supposed to have a mentor but the people that you really see as your mentors are just your uncles and older uncles and shit… but if you feel like you can make a path outside of that, if you feel like you can make a path that might take them off of the shit that they are on then you're not gonna take that advice you just gone be raising yourself. I did pretty much raise myself for a point in time. My Pops was there when I was younger but the older I got, I wanna say around 7, he just started to disappear…Moms can only do so much. She did her part to the fullest but you gotta learn how to be a man on your own.

/CW: So do you feel that you can learn as much as you could from someone who has a profession or perspective outside of what you're doing?

HV: I feel that anybody who has a sense of decency has some type of valuable information to give to somebody. I’ll chop it up with a homeless dude on the corner because I might learn something about life. It might not be financial literacy but he sees stuff on a daily basis that I don't see so there's probably things that I can't even comprehend that he sees on a regular basis so I definitely try not to close out every voice because you might miss your blessing but I definitely dont recieve every opinion as a fact because that’s how you fuck your blessing up…you weren’t meant to accomplish what they were supposed to accomplish but they might’ve sparked the idea for you to make it happen and now you get to change the next 30 peoples’ lives..

/CW: That brings me to my next point of that ‘hustler’s phase’; you get to that point where you know what you wanna do, you're willing to be dedicated, go broke for it, all of that, but then a lot of people get to that point of mastering that hustler’s phase but there's a lack of maintenance of it…

Huey V describes the intention that he puts into his artistry and the real life ease that comes with the concept of quality over quantity, while also admitting to sleepless nights for the benefit of meeting deadlines and being thorough with his production.

/CW: You must be really involved in the other elements of making a song or an album; the production…

HV: .. If I can be. I wouldn't say that I'm a producer or anything like that but I record, I mix myself if I can, [Young] Guru masters everything, I can't do that part. That's his bag. But I mix everything, I record everything…I try to be as hands on as possible with absolutely everything..

/CW: The Midwest culture, particularly the Milwaukee culture, is to be so hands-on. Everyone wants to be independent, because most don't understand the true art of collaboration yet, we are starting to but we are not there yet. Is that why [you are hands on] or is it that you do understand that art but you still want to be educated on [the production]?

HV: Imma be honest with you, I like collaboration, I like teamwork; Working with other people and seeing them get their satisfaction out of it and seeing their dreams come true as well as mine means more to me than just seeing my own shit…but at the same time being in Milwaukee, we’re the home of the warehouses so yes of course Imma try to do everything that I can, I don't wanna be a one-trick pony, but I don't wanna be a ‘Jack of all trades and a master of none’ either so I am hyper-focused on music..

With WHMG having had rappers like Casanova on their roster, Huey V feels a sense of pride with the weight of his label. His courage is greatly accredited to the wide range of influence from Kanye West to Amy Winehouse. Growing up, his family, in parallel to living in mIlwaukee as a whole, was a melting pot of musical tastes. Along with having a background in orchestra, the young artist has been fortunate to have an open ear and appreciation for sound. He brings up Frank Ocean as an example of how introducing a new way of approaching music to someone with a more biased ear can leave them in awe.

/CW: Did you always want to be signed? Was that the height, or was it similar to going to a 2 year college, ‘I'll do this for a little while, get the resources, learn the business, and then go back to being in my own lane, independently?’ 

HV: It's a mixture of it all. When I was a kid I thought ‘cool maybe i'll get signed,’ the older that I got the more I understood the importance of independence…I swore I was gonna be independent..and then Corona hit.

/CW: You were signed during the Pandemic right?

HV: Yea, actually during that MF…I left for New York on February 7th and I came back the next day and I think Milwaukee either shut down that same month or in March…after that time passed they flew me out to Miami and that's when we made it happen. But when the Pandemic hit I was like ‘dammmmnn’ because all the jobs were shut down, it was either hustling or signing…

/CW: You speak a lot about Divine Timing using subtle words in your music like ‘divine timing, letting God work,’ even the name of your last EP, “As Above,” and your next one, “So Below.” Those are very spiritual statements…

HV: I call it the Matrix, where I've been able to pinpoint that if certain things didn't happen then other things wouldn't have happened the way that they did. In my head everything is prewritten…

/CW: How has that wisdom played a part in how you've grown as a person? In your song “After The Deal” you spoke a lot about having to leave people behind. That survivor's guilt is very real. How did you handle that ego death? Was it a super low moment or was it gradual?

HV: I am used to it. You lose a lot of people. It's easier when they are still around.. It's by your choice and not by life's timing so it's been a bit easier because I understand the value of having to let certain people go to get to where I gotta get to...

/CW: There was a line in your song where you said “I got the deal after the bill collector called..” Was that a true statement?

HV: Ha ha! Aight so what really happened was the bill collector called..Right after the bill collector called was the first time I spoke to Bleek. I didn't even get the heads up that he was finna be callin. When that  happened he told me “lil nigga you on right now, you just gotta prove to me that you can keep doing this.” That was literally the song that I made after that…it really makes you appreciate the value of your life, the highs and the lows..

Tell me how YOU feel about “ After The Deal ” Milwaukee. And check out his previous works while you're at it:  “As Above” … “So Below” coming soon.

/Naomi-Re’a for CW

Partnership Content - Artist Eats: SistaStrings at Villa Terrace

Partnership Content - Artist Eats

SistaStrings at Villa Terrace

We met in early May 2021 at Villa Terrace. The unusually cold day was even colder as we were situated on Milwaukee’s east side across the street from our lakefront. 

On this particular day, Monique Ross (older by 2 years) and Chauntee Ross are exhausted but ecstatic. Just 2 days prior, they announced their farewell show before moving permanently to Nashville, TN. Their departure is a harsh reminder of the importance of creating and cultivating an arts community that allows artists to flourish and get paid. 

Their farewell show sold out in 72 hours. Another reminder of how incredible their contribution is to Milwaukee’s music scene and how much we’ll miss them. As of today’s writing, they’re doing well in Nashville including recently sharing the stage with Thee Brandi Carlile. 

Not too shabby for the Queens of Strings. Not too shabby at all.

It’s hard to encompass all that is SistaStrings in a 10-minute video. Our conversation over FlourGirl and Flame pizza and drinks from Vibez Creative Arts Space navigated the journey of 2 black women who’ve made a home in classical music with a bit of gospel and a bit of soul. 

Here’s our interview.

Rissa Fam - Eat ft. Munch Lauren

One thing about me is that I love a good ol classic ratchet banger, and that’s what EAT is. Now

this nice little hidden gem came out in 2010, but I recently discovered it last week. The Milwaukee bop by Rissa Fam and Munch Lauren currently has over 1 million streams on the internet, and was released with a colorful hyped music video on Youtube. I’m a firm lover of music, and I will always appreciate party music; it just gets you hype and makes you celebrate yourself. When I hear that I try to activate my Megan knees in the comfort of my home (keyword try). The music video was shot so simple, but it was effective. I mean who wouldn’t wanna see twerking, good vibes, and good food in a music video? Sounds like a good time to me. It’s dope to see more styles of music coming out of artists from Milwaukee, we just need to get everyone connected together. Rissa Fam is definitely an artist who embraces the good vibes in Milwaukee, and puts into her music. She also did a song this year with Milwaukee artist Chicken P called Money. You can check out more of her music on her Youtube.

Adrienne/ For CW

Bay View’s collaborative fall festival, Beet Street, celebrates live music, community building and film with seasonal drinks, foods and an artists market

*Info provided by Julia Bellair

On Saturday, October 9th, 2021, Cactus Club, Palomino Bar and Goodkind will team up to host the 5th annual Beet Street Fall Festival. This family-friendly event runs noon-6pm with an indoor after-party to follow.

Cactus Club has curated a lineup of rising stars: Chicago's modern disco darling, Ric Wilson, will headline with direct support from LA psych-rockers Frankie & The Witch Fingers. Fantastic Milwaukee artists CREDENTIALS and Clayton will also play. CREDENTIALS is a noisy, math rock 4-piece fronted by Cat Ries (No/No, Rio Turbo, Pleasure Thief) with a debut album coming out this November. Clayton continues to turn up the heat into fall. A distinguished vocalist, Clayton crafts a broad range of stylized R&B with lush harmonies. Intergenerational quintet Mariachi Zomara will kick things off complimented by the DJ stylings of Cozmiika between sets. 

This block party celebrates community organizations doing incredible work across the city and state. Teens Grow Greens, Girls Rock Camp, Milwaukee High School of the Arts, Midwest Renewable Energy Association and Bayview Historical Society will all have a presence in addition to several mutual aid groups and health resource centers. Interactive games from our friends at Music Go Round. 

The Beet Street Music Video Showcase highlights a wide-range of filmmakers in Milwaukee and beyond through a curated selection of music videos, documentary shorts and more. This showcase will screen on loop in the live room of Cactus Club throughout the day.  

Honeypie’s Great Midwestern Pie Championship is a crucial part of the festivities. Bake and enter your favorite pie to win prizes! Outstanding seasonal cocktails will be available from all three establishments in addition to caramel apples, roasted corn and food from Frida’s Cocina Taco Truck, Twisted Plants and more. To round out the party, there will be an artists market that includes book/zine vendors, farmers, local honey purveyors, custom clothing and a punk rock rummage sale. 

 Beet Street Fall Festival provides a warm and welcoming atmosphere for all to enjoy. The event aims to connect people, communities and causes in a space that enriches all senses. There will be an emphasis on youth participation and activities. As is the case with all Cactus Club events, eclectic music programming will be at the forefront of this fall party.

Learn more

Website: www.cactusclubmilwaukee.com

Music on the Beerline Trail: /CW Interview w/ Rosalynn Wolfe & Ray Nitti

click here for more information

Mace supreme & YN Jay - Jumanji

We heard word play and beats that crack (no we’re not talking backs) were the new wave, obviously Mace Supreme & YN Jay got the memo. And please don’t even get me started on the song cover, I saw it and was like “yeah I don’t even need to hear the song, I already like it”, I almost made it my screensaver. 

Guys, “Guess the I’m the man of her dreams, call me Fred Krueger” is the bar of the year in my book and no I’m not biased because my favorite horror movie is Nightmare on Elm Street BUT for OTHER reasons :))!! Hey Mace Supreme or maybe even YN Jay, since you guys are so good at making analogies, making things simple and make sense and stuff, I was wondering if you wouldn’t mind giving my English teacher a few lessons. Nah but fr this bar and many others COMBINED with this wild beat are too hot to handle, they’ll make you make that one face and I KNOW y’all know what I'm talkin about.

THIS FACE!

Don’t be lame, give this a listen right fast and let us know if this is making it to your summer playlist. 

Instagram: MaceSupreme

/CW Maxp

B Justice - The Kee [album submission]

Looking for hot new tracks to bump with your hair blowing in the wind while you’re tippin on        I 95? Well, your search ends here because B Justice is determined to gas you TF up with his new and upcoming album ‘THE KEE’. 

The album features artists such as Sawyer Gibson, Ray Justice, Troy Tyler, Destinee Lynn, Young Focus, Richon Martena, Mac Hefner, Baby Drew, Jadakiss and Godxilla. Giving major deja vu moments with the sick lyrics, throwback melodies and flyer than fly a** vocals.  

Sit back, relax and jam as B Justice applies pressure and takes you on a journey of rhythm and base, he’s sure to show you somethin’ you ain’t used to! The hit single of the album ‘Stand in the light’ features vocals by Troy Tyler that gives the summer block party, beaming sun, getting money quickness with a hint of latin spice type vibe that’s for sure easy to get down with. Like ‘In the heights’ if you will. Play this for any little lady you’re with and she’s sure to start shaking her hips in a tango fashion.

Take a listen and let us know if he showed you yet that he’s purely the essence of the best.

Spotify: B. Justice

Instagram: @iambjustice

Youtube: bjusticemusic

Web: Iambjustice.com

/CW Maxp