Entertainment: Juneteenth, Summerfest and a Weekend of Fun » Urban Milwaukee

Summerfest is finally here! The world’s largest music festival is back and will bring hundreds of performers and thousands of fans to the city. But if navigating crowds and bouncing from stage to stage isn’t your thing, there’s still plenty of other events to check out. Pet Walk MKE will raise funds for the Wisconsin Humane Society’s programming down by the lake with live music, food, and activities like face painting, runs, talent shows and more. Milwaukee will also throw its annual Juneteenth Day Celebration on Martin Luther King Drive, a block party featuring live music, food, activities and more that will coincide with the annual Jubilee Parade.

June 18-20: Summerfest Weekend One

The Big Gig has arrived! Summerfest, the world’s largest music festival, is here and will once again take place over three weekends at Henry Maier Festival Park. Each weekend will be packed full of live music on both free and ticketed stages, entertainment such as skateboarding and BMX demonstrations, vendors and more. Music highlights for weekend one include Third Eye Blind, Styx, Braid and more. Be sure to catch featured local acts like Tiny Voices, Trapper Schoepp and Barely Civil and don’t forget to check the Summerfest website to find out about admission promotions like the Neighborhood House Food Drive on Friday, where guests who bring three shelf-stable food items for donation between noon and 3 p.m. will be admitted for free.

June 19: Juneteenth Day Celebration

Milwaukee’s annual celebration of African American freedom and achievement will bring games, soul food, live music and more to several blocks on N. Martin Luther King Drive from 9 a.m. to 4 p.m. The celebration will also feature a parade with floats, dance teams, marching bands and more, kicking off at 9 a.m. The parade will start at 8th Street and travel southeast on Atkinson Avenue and then south down Martin Luther King Drive. For more information, visit the Juneteenth Milwaukee website.

June 20: Pet Walk MKE

The Wisconsin Humane Society’s largest run/walk and outdoor celebration will bring pets and their owners to Veterans Park for an event that helps fund the organization’s programming. On top of the timed 5k run/walk and the one-mile stroll, guests can enjoy live music, family-friendly activities, food vendors and more. Guests can also participate in raffles and enter their furry friends into costume contests and talent shows. Pet Walk MKE is free to attend and 8:30 a.m. to 12 p.m. For more info, visit the Wisconsin Humane Society’s website.

June 21: Milwaukee Makers Market

Over 40 small local businesses will set up shop at the American Family Field as part of the Milwaukee Makers Market. From 10 a.m. to 4 p.m., guests can shop handmade goods, furniture, vintage clothing and more at the Brewers’ stadium. For more information, visit the Milwaukee Makers Market website.

June 21: Keg Stand Up

Lakefront Brewery will transform into a comedy club for the evening as part of the brewery’s recurring Keg Stand Up event series. A lineup of comedians will take to the stage from 7 p.m. to 8:30 p.m., delivering laughs while guests can order from the brewery’s full lineup of craft beverages. And while the brewery’s kitchen will be closed, those who get hungry can still order snacks from the bar. For more information and to purchase tickets, visit Lakefront Brewery’s website.

June 21: Cafe Sopra Sare

If at this point you haven’t had your fill of live music outdoors, the Villa Terrace’s Sopra Mare daytime concert series is back, bringing live music performances to the museum’s courtyard. The free concert series will kick off with a performance by classical guitarist Louis Cucunato. During the concert, the museum and gardens will be free to access. Villa Terrace will also offer complimentary coffee and encourages guests to bring their own coffee, if preferred. Sopra Mare will run from 10:30 a.m. to 12:30 a.m.