Michael Holloway
Entertainment

On Your Marks, Get Set, Beer Run!

Plus: Bay View Gallery Night and Downtown Dining Week.

By - May 29th, 2025 03:27 pm
Runners prepare for the 2019 Beer Run. Photo by Jeramey Jannene.

Runners prepare for the 2019 Beer Run. Photo by Jeramey Jannene.

Street festival season is upon us!

Kicking off a Milwaukee summer filled with festivals is Locust Street Festival, a free to attend event featuring four live music stages and the famous Beer Run. Bay View Gallery Night and Bay View Jazz Festival will turn various businesses around the neighborhood into art venues and Festa Italiana will celebrate Italian food, music, art and more at the Henry Maier Festival Park.

May 29-June 5: Downtown Dining Week

Enjoy some of the best food that Milwaukee has to offer throughout Downtown Dining Week, an event that offers multi-course deals at over 25 restaurants. Offers include $15 or $25 lunch deals or $35, $45 or $55 dinner deals. Participating restaurants include Bacchus, Tupelo Honey, Flourchild Pizza and more. For more information, including a full list of participating restaurants, visit the Milwaukee Downtown website.

May 30: Bay View Gallery Night & Bay View Jazz Festival

Over 70 businesses located throughout the Bay View neighborhood will transform their spaces into miniature galleries and venues – welcoming artists, performers and vendors to show off their work while business carries on as usual. Running in conjunction with Bay View Gallery Night is the Bay View Jazz Festival, where businesses such as Cache Cider and 1840 Brewing Co. will host varying lineups of jazz musicians throughout the evening. Both events are free to attend. For more information on participating venues, visit the Bay View Gallery Night’s website.

May 30-June 1: Festa Italiana

A bocce tournament, singing competition and best sauce competition are just a few of the experiences available to guests at Festa Italiana, a celebration of Italian culture hosted at the Henry Maier Festival Park. Dozens of vendors will serve classic Italian fare while acts like the Milwaukee Mandolin Orchestra and Frank Lamphere & His Rat Pack Jazz Quintet perform on two different stages. Italian Idol will pit aspiring singers against one another for the chance to win $1000, and guests can enjoy some of the first fireworks of Milwaukee’s festival season on May 31 at 10:30 p.m. Festa Italiana will run from 5 p.m. to 10 p.m. on Friday, from 11 a.m. to 11 p.m. on Saturday and 12 p.m. to 9 p.m. on Sunday. For more information, visit the Festa Italiana website.

May 31: The Great Riverwest Rummage Sale

Over 200 vendors will set up shop at the Riverwest neighborhood’s largest rummage sale. Located outside of Art Bar and Wonderland, The Great Riverwest Rummage Sale will offer anything from vintage clothing, comic books, home decor and more. A lineup of live performers will provide ambience while you shop, and a lineup of food trucks will provide snacks. Art Bar and Wonderland will both be open as well, and Art Bar’s patio Satellite Bar will offer a quick way to grab a Bloody Mary while you shop. The Great Riverwest Rummage Sale is free to attend and will run from 9 a.m. to 5 p.m.

June 1: Locust Street Festival

The first street festival of the summer is here! The 46th Annual Locust Street Festival will feature four live music stages from 12 p.m. to 8 p.m. as well as vendors, food trucks and more. The Locust Street Beer Run is back and participants will either run or walk a 1.6-mile route with four beer stops along the way. Locust Street Festival is free to attend. For more information, visit the Locust Street Festival website.

June 1: UPAF Ride for the Arts

Hop on your bike and ride for a good cause as part of the UPAF Ride for the Arts. This fundraising bike ride takes participants through a unique route that utilizes Interstate 794, taking riders from downtown Milwaukee to Cudahy and back. So far, the 20-mile ride has raised over $300,000 for local art. For more information, to register or to donate, visit the UPAF website.

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